Structure

Physi-Chem Properties

Molecular Weight:  592.22
Volume:  545.415
LogP:  0.635
LogD:  -0.209
LogS:  -3.745
# Rotatable Bonds:  1
TPSA:  195.35
# H-Bond Aceptor:  13
# H-Bond Donor:  4
# Rings:  8
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.207
Synthetic Accessibility Score:  7.858
Fsp3:  0.862
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.387
MDCK Permeability:  4.736915434477851e-05
Pgp-inhibitor:  0.201
Pgp-substrate:  0.869
Human Intestinal Absorption (HIA):  0.852
20% Bioavailability (F20%):  0.998
30% Bioavailability (F30%):  0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.137
Plasma Protein Binding (PPB):  42.6890983581543%
Volume Distribution (VD):  0.583
Pgp-substrate:  50.458518981933594%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.977
CYP2C19-inhibitor:  0.007
CYP2C19-substrate:  0.489
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.008
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.052
CYP3A4-inhibitor:  0.476
CYP3A4-substrate:  0.215

ADMET: Excretion

Clearance (CL):  1.995
Half-life (T1/2):  0.488

ADMET: Toxicity

hERG Blockers:  0.072
Human Hepatotoxicity (H-HT):  0.993
Drug-inuced Liver Injury (DILI):  0.977
AMES Toxicity:  0.078
Rat Oral Acute Toxicity:  0.921
Maximum Recommended Daily Dose:  0.835
Skin Sensitization:  0.586
Carcinogencity:  0.141
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.932

Download Data

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

  Natural Product: NPC167044

Natural Product ID:  NPC167044
Common Name*:   Schisandilactone H
IUPAC Name:   n.a.
Synonyms:   Schisandilactone H
Standard InCHIKey:  QJLSZCHBNGDYBO-JVWCCWGQSA-N
Standard InCHI:  InChI=1S/C29H36O13/c1-11-17-19(38-20(11)34)28(37)21-24(3,22(35)25(28,4)36)14(31)8-26-9-27-13(6-5-12(26)18(33)29(21,41-17)42-26)23(2,10-30)39-15(27)7-16(32)40-27/h11-13,15,17-19,21,30,33,36-37H,5-10H2,1-4H3/t11-,12+,13-,15+,17+,18+,19-,21+,23-,24-,25-,26-,27+,28-,29+/m0/s1
SMILES:  C[C@H]1[C@@H]2[C@@H]([C@@]3([C@H]4[C@](C)(C(=O)C[C@]56C[C@@]78[C@@H](CC[C@@H]5[C@H]([C@@]4(O2)O6)O)[C@](C)(CO)O[C@@H]7CC(=O)O8)C(=O)[C@]3(C)O)O)OC1=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1215357
PubChem CID:   46918833
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000513] Eicosanoids
          • [CHEMONTID:0000514] Prostaglandins and related compounds

*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
NPO7850 Schisandra propinqua Species Schisandraceae Eukaryota n.a. stem n.a. DOI[10.1002/cjoc.20010190319]
NPO7850 Schisandra propinqua Species Schisandraceae Eukaryota n.a. stem n.a. DOI[10.1016/j.tet.2008.10.079]
NPO7850 Schisandra propinqua Species Schisandraceae Eukaryota n.a. stem n.a. PMID[11395273]
NPO7850 Schisandra propinqua Species Schisandraceae Eukaryota n.a. stem n.a. PMID[18536373]
NPO7850 Schisandra propinqua Species Schisandraceae Eukaryota aerial parts Erlang Mountain area of Sichuan Province, China 2007-SEP PMID[19413342]
NPO7850 Schisandra propinqua Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[20681569]
NPO7850 Schisandra propinqua Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9834 Veronica austriaca Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6903 Lecanora straminea Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7128 Cynthia savignyi n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO7374 Seseli montanum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7850 Schisandra propinqua Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11167 Prunus ssiori Species Rosaceae 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 IC50 > 100000.0 nM PMID[527274]
NPT139 Cell Line HT-29 Homo sapiens IC50 > 100000.0 nM PMID[527274]
NPT111 Cell Line K562 Homo sapiens IC50 > 100000.0 nM PMID[527274]

☑ 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 NPC167044 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
0.9899 High Similarity NPC176756
0.9608 High Similarity NPC182185
0.951 High Similarity NPC217041
0.9423 High Similarity NPC98870
0.9406 High Similarity NPC168890
0.9314 High Similarity NPC469787
0.9314 High Similarity NPC290247
0.9314 High Similarity NPC469788
0.9223 High Similarity NPC278693
0.9223 High Similarity NPC220773
0.9029 High Similarity NPC41674
0.9029 High Similarity NPC228311
0.9029 High Similarity NPC469441
0.8857 High Similarity NPC329876
0.8654 High Similarity NPC469350
0.8627 High Similarity NPC274695
0.8571 High Similarity NPC177518
0.8571 High Similarity NPC154962
0.8571 High Similarity NPC18044
0.8571 High Similarity NPC169089
0.8571 High Similarity NPC132304
0.8571 High Similarity NPC114365
0.8571 High Similarity NPC123070
0.8571 High Similarity NPC18433
0.8571 High Similarity NPC88890
0.8462 Intermediate Similarity NPC162024
0.8381 Intermediate Similarity NPC292803
0.8173 Intermediate Similarity NPC328180
0.8173 Intermediate Similarity NPC278028
0.8056 Intermediate Similarity NPC473526
0.8056 Intermediate Similarity NPC473701
0.7921 Intermediate Similarity NPC470009
0.7899 Intermediate Similarity NPC144625
0.7886 Intermediate Similarity NPC224623
0.7869 Intermediate Similarity NPC469351
0.7826 Intermediate Similarity NPC475490
0.7815 Intermediate Similarity NPC186339
0.7658 Intermediate Similarity NPC166079
0.7647 Intermediate Similarity NPC314364
0.7642 Intermediate Similarity NPC13071
0.7623 Intermediate Similarity NPC11732
0.7593 Intermediate Similarity NPC211087
0.7568 Intermediate Similarity NPC100078
0.7545 Intermediate Similarity NPC213528
0.7545 Intermediate Similarity NPC244969
0.75 Intermediate Similarity NPC306776
0.7477 Intermediate Similarity NPC470191
0.7476 Intermediate Similarity NPC31349
0.7455 Intermediate Similarity NPC178853
0.7453 Intermediate Similarity NPC472237
0.7453 Intermediate Similarity NPC472238
0.7436 Intermediate Similarity NPC470115
0.7436 Intermediate Similarity NPC470116
0.7426 Intermediate Similarity NPC157328
0.7419 Intermediate Similarity NPC172823
0.7411 Intermediate Similarity NPC88469
0.7391 Intermediate Similarity NPC475463
0.7379 Intermediate Similarity NPC470657
0.7377 Intermediate Similarity NPC1538
0.7353 Intermediate Similarity NPC473791
0.7328 Intermediate Similarity NPC473062
0.7308 Intermediate Similarity NPC51662
0.7295 Intermediate Similarity NPC192309
0.7288 Intermediate Similarity NPC79193
0.7273 Intermediate Similarity NPC253995
0.7232 Intermediate Similarity NPC470172
0.7222 Intermediate Similarity NPC217567
0.7222 Intermediate Similarity NPC470424
0.7222 Intermediate Similarity NPC76136
0.7222 Intermediate Similarity NPC329713
0.7196 Intermediate Similarity NPC474699
0.7182 Intermediate Similarity NPC263674
0.7182 Intermediate Similarity NPC58267
0.7182 Intermediate Similarity NPC261372
0.7172 Intermediate Similarity NPC214030
0.7172 Intermediate Similarity NPC83108
0.7168 Intermediate Similarity NPC471253
0.7168 Intermediate Similarity NPC473406
0.7167 Intermediate Similarity NPC179429
0.7157 Intermediate Similarity NPC212340
0.7143 Intermediate Similarity NPC298266
0.7143 Intermediate Similarity NPC259654
0.7097 Intermediate Similarity NPC42747
0.7091 Intermediate Similarity NPC476728
0.7087 Intermediate Similarity NPC474266
0.7083 Intermediate Similarity NPC277583
0.7064 Intermediate Similarity NPC206878
0.7059 Intermediate Similarity NPC97002
0.7037 Intermediate Similarity NPC474065
0.7 Intermediate Similarity NPC215570
0.6992 Remote Similarity NPC163693
0.6992 Remote Similarity NPC147635
0.6991 Remote Similarity NPC478181
0.699 Remote Similarity NPC475849
0.697 Remote Similarity NPC179922
0.6957 Remote Similarity NPC470167
0.6952 Remote Similarity NPC478111
0.6937 Remote Similarity NPC116683
0.6937 Remote Similarity NPC193785
0.6931 Remote Similarity NPC475616
0.693 Remote Similarity NPC471254
0.6897 Remote Similarity NPC215408
0.6893 Remote Similarity NPC216941
0.6891 Remote Similarity NPC469824
0.6887 Remote Similarity NPC476717
0.687 Remote Similarity NPC475376
0.687 Remote Similarity NPC470117
0.687 Remote Similarity NPC473148
0.6869 Remote Similarity NPC215030
0.6869 Remote Similarity NPC125164
0.6869 Remote Similarity NPC477867
0.6864 Remote Similarity NPC208333
0.6864 Remote Similarity NPC227879
0.6855 Remote Similarity NPC142882
0.6852 Remote Similarity NPC200580
0.6847 Remote Similarity NPC305808
0.6842 Remote Similarity NPC67296
0.6838 Remote Similarity NPC203974
0.6832 Remote Similarity NPC70996
0.6832 Remote Similarity NPC474003
0.6818 Remote Similarity NPC161035
0.6818 Remote Similarity NPC219058
0.6818 Remote Similarity NPC256618
0.6818 Remote Similarity NPC475788
0.6807 Remote Similarity NPC106760
0.68 Remote Similarity NPC228411
0.6797 Remote Similarity NPC2757
0.6786 Remote Similarity NPC474297
0.678 Remote Similarity NPC202898
0.678 Remote Similarity NPC475319
0.678 Remote Similarity NPC92890
0.6759 Remote Similarity NPC33398
0.6757 Remote Similarity NPC470423
0.6748 Remote Similarity NPC475238
0.6729 Remote Similarity NPC92139
0.6726 Remote Similarity NPC74466
0.6726 Remote Similarity NPC304445
0.6726 Remote Similarity NPC472273
0.6726 Remote Similarity NPC311904
0.6726 Remote Similarity NPC236580
0.6726 Remote Similarity NPC471241
0.6724 Remote Similarity NPC107385
0.6723 Remote Similarity NPC220836
0.6723 Remote Similarity NPC92297
0.6723 Remote Similarity NPC233433
0.6723 Remote Similarity NPC228190
0.6723 Remote Similarity NPC94086
0.6723 Remote Similarity NPC273002
0.6723 Remote Similarity NPC236753
0.6723 Remote Similarity NPC473817
0.6721 Remote Similarity NPC308858
0.6721 Remote Similarity NPC475537
0.672 Remote Similarity NPC329008
0.672 Remote Similarity NPC317635
0.6718 Remote Similarity NPC42206
0.6698 Remote Similarity NPC291310
0.6697 Remote Similarity NPC477443
0.6697 Remote Similarity NPC477440
0.6696 Remote Similarity NPC287354
0.6696 Remote Similarity NPC62407
0.6696 Remote Similarity NPC21897
0.6694 Remote Similarity NPC477489
0.6693 Remote Similarity NPC129992
0.6667 Remote Similarity NPC122083
0.6667 Remote Similarity NPC102156
0.6667 Remote Similarity NPC182740
0.6667 Remote Similarity NPC148740
0.6667 Remote Similarity NPC476189
0.6667 Remote Similarity NPC256104
0.6667 Remote Similarity NPC211845
0.6667 Remote Similarity NPC292775
0.6667 Remote Similarity NPC470243
0.6667 Remote Similarity NPC239938
0.6641 Remote Similarity NPC475389
0.6641 Remote Similarity NPC473838
0.664 Remote Similarity NPC319570
0.6639 Remote Similarity NPC472079
0.6639 Remote Similarity NPC469826
0.6639 Remote Similarity NPC110701
0.6639 Remote Similarity NPC102619
0.6639 Remote Similarity NPC224414
0.6638 Remote Similarity NPC80144
0.6637 Remote Similarity NPC91771
0.6637 Remote Similarity NPC476009
0.6637 Remote Similarity NPC475785
0.6637 Remote Similarity NPC475765
0.6637 Remote Similarity NPC142529
0.6637 Remote Similarity NPC126156
0.6636 Remote Similarity NPC246173
0.6636 Remote Similarity NPC51267
0.6636 Remote Similarity NPC477442
0.6636 Remote Similarity NPC477444
0.6636 Remote Similarity NPC477433
0.6612 Remote Similarity NPC474750
0.6612 Remote Similarity NPC472003
0.661 Remote Similarity NPC291643
0.661 Remote Similarity NPC44004
0.661 Remote Similarity NPC474101
0.6609 Remote Similarity NPC20028
0.6606 Remote Similarity NPC53158

  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 NPC167044 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
0.8571 High Similarity NPD4056 Clinical (unspecified phase)
0.8571 High Similarity NPD4057 Clinical (unspecified phase)
0.6991 Remote Similarity NPD1700 Approved
0.681 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6602 Remote Similarity NPD4802 Phase 2
0.6602 Remote Similarity NPD4238 Approved
0.6538 Remote Similarity NPD7078 Approved
0.6512 Remote Similarity NPD7492 Approved
0.6462 Remote Similarity NPD6616 Approved
0.6457 Remote Similarity NPD6059 Approved
0.6457 Remote Similarity NPD6054 Approved
0.6412 Remote Similarity NPD8293 Discontinued
0.6364 Remote Similarity NPD7736 Approved
0.6357 Remote Similarity NPD6370 Approved
0.6281 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6279 Remote Similarity NPD6016 Approved
0.6279 Remote Similarity NPD6015 Approved
0.6231 Remote Similarity NPD5988 Approved
0.6218 Remote Similarity NPD8139 Approved
0.6218 Remote Similarity NPD8084 Approved
0.6218 Remote Similarity NPD8083 Approved
0.6218 Remote Similarity NPD8085 Approved
0.6218 Remote Similarity NPD8138 Approved
0.6218 Remote Similarity NPD8086 Approved
0.6218 Remote Similarity NPD8082 Approved
0.6202 Remote Similarity NPD6319 Approved
0.6167 Remote Similarity NPD8275 Approved
0.6167 Remote Similarity NPD8276 Approved
0.6154 Remote Similarity NPD8267 Approved
0.6154 Remote Similarity NPD8268 Approved
0.6154 Remote Similarity NPD8266 Approved
0.6154 Remote Similarity NPD8269 Approved
0.6129 Remote Similarity NPD6371 Approved
0.6116 Remote Similarity NPD8081 Approved
0.6098 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6074 Remote Similarity NPD7319 Approved
0.6066 Remote Similarity NPD8393 Approved
0.6 Remote Similarity NPD6033 Approved
0.597 Remote Similarity NPD7507 Approved
0.5969 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5948 Remote Similarity NPD8171 Discontinued
0.5941 Remote Similarity NPD896 Approved
0.5941 Remote Similarity NPD898 Approved
0.5941 Remote Similarity NPD897 Approved
0.5906 Remote Similarity NPD6882 Approved
0.5887 Remote Similarity NPD6412 Phase 2
0.5859 Remote Similarity NPD8133 Approved
0.5849 Remote Similarity NPD3702 Approved
0.5846 Remote Similarity NPD6009 Approved
0.5821 Remote Similarity NPD8328 Phase 3
0.5794 Remote Similarity NPD6373 Approved
0.5794 Remote Similarity NPD6372 Approved
0.5781 Remote Similarity NPD8297 Approved
0.578 Remote Similarity NPD7329 Approved
0.5763 Remote Similarity NPD5282 Discontinued
0.576 Remote Similarity NPD8307 Discontinued
0.576 Remote Similarity NPD8140 Approved
0.5736 Remote Similarity NPD4632 Approved
0.5728 Remote Similarity NPD229 Approved
0.5727 Remote Similarity NPD6928 Phase 2
0.5714 Remote Similarity NPD7320 Approved
0.5714 Remote Similarity NPD3670 Clinical (unspecified phase)
0.5714 Remote Similarity NPD3669 Approved
0.5703 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5703 Remote Similarity NPD6649 Approved
0.5703 Remote Similarity NPD6650 Approved
0.5691 Remote Similarity NPD8300 Approved
0.5691 Remote Similarity NPD8301 Approved
0.5683 Remote Similarity NPD5956 Approved
0.568 Remote Similarity NPD6402 Approved
0.568 Remote Similarity NPD6675 Approved
0.568 Remote Similarity NPD5739 Approved
0.568 Remote Similarity NPD7128 Approved
0.5676 Remote Similarity NPD1780 Approved
0.5676 Remote Similarity NPD1779 Approved
0.5672 Remote Similarity NPD6921 Approved
0.5672 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5669 Remote Similarity NPD8305 Approved
0.5669 Remote Similarity NPD8306 Approved
0.5669 Remote Similarity NPD8132 Clinical (unspecified phase)
0.566 Remote Similarity NPD3181 Approved
0.563 Remote Similarity NPD8080 Discontinued
0.5625 Remote Similarity NPD8087 Discontinued
0.5625 Remote Similarity NPD6435 Approved
0.5625 Remote Similarity NPD4634 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