Structure

Physi-Chem Properties

Molecular Weight:  432.14
Volume:  440.338
LogP:  6.348
LogD:  4.807
LogS:  -7.103
# Rotatable Bonds:  11
TPSA:  52.6
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.281
Synthetic Accessibility Score:  2.909
Fsp3:  0.478
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.333
MDCK Permeability:  1.940579568326939e-05
Pgp-inhibitor:  0.974
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.012
30% Bioavailability (F30%):  0.748

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.006
Plasma Protein Binding (PPB):  101.20073699951172%
Volume Distribution (VD):  0.991
Pgp-substrate:  0.8284972906112671%

ADMET: Metabolism

CYP1A2-inhibitor:  0.739
CYP1A2-substrate:  0.145
CYP2C19-inhibitor:  0.912
CYP2C19-substrate:  0.139
CYP2C9-inhibitor:  0.953
CYP2C9-substrate:  0.884
CYP2D6-inhibitor:  0.152
CYP2D6-substrate:  0.101
CYP3A4-inhibitor:  0.8
CYP3A4-substrate:  0.668

ADMET: Excretion

Clearance (CL):  5.903
Half-life (T1/2):  0.008

ADMET: Toxicity

hERG Blockers:  0.012
Human Hepatotoxicity (H-HT):  0.775
Drug-inuced Liver Injury (DILI):  0.948
AMES Toxicity:  0.064
Rat Oral Acute Toxicity:  0.692
Maximum Recommended Daily Dose:  0.018
Skin Sensitization:  0.936
Carcinogencity:  0.815
Eye Corrosion:  0.006
Eye Irritation:  0.089
Respiratory Toxicity:  0.083

Download Data

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

  Natural Product: NPC32356

Natural Product ID:  NPC32356
Common Name*:   KWTCTHJCQNSERL-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  KWTCTHJCQNSERL-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C23H28O4S2/c1-16(2)13-22(24)26-12-6-5-7-18-8-10-20(28-18)21-11-9-19(29-21)15-27-23(25)14-17(3)4/h8-11,16-17H,6,12-15H2,1-4H3
SMILES:  CC(C)CC(=O)OCCC#Cc1ccc(c2ccc(COC(=O)CC(C)C)s2)s1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3343901
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002021] Bi- and oligothiophenes

*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
NPO33375 eclipata prostrata Species n.a. n.a. aerial parts n.a. n.a. PMID[25443644]

☑ 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
NPT1592 Individual Protein Dipeptidyl peptidase IV Homo sapiens IC50 = 750.0 nM PMID[545402]

☑ 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 NPC32356 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
0.8545 High Similarity NPC475086
0.7946 Intermediate Similarity NPC472172
0.7857 Intermediate Similarity NPC472171
0.7565 Intermediate Similarity NPC472170
0.7154 Intermediate Similarity NPC475082
0.7094 Intermediate Similarity NPC173019
0.7043 Intermediate Similarity NPC474934
0.7027 Intermediate Similarity NPC2751
0.6967 Remote Similarity NPC190955
0.696 Remote Similarity NPC221877
0.6875 Remote Similarity NPC220893
0.6696 Remote Similarity NPC89377
0.6574 Remote Similarity NPC8981
0.6529 Remote Similarity NPC475115
0.6518 Remote Similarity NPC58616
0.6491 Remote Similarity NPC304760
0.6435 Remote Similarity NPC173443
0.6434 Remote Similarity NPC210092
0.6387 Remote Similarity NPC175376
0.6379 Remote Similarity NPC185501
0.6364 Remote Similarity NPC146351
0.6341 Remote Similarity NPC301943
0.6341 Remote Similarity NPC474365
0.6339 Remote Similarity NPC270507
0.6325 Remote Similarity NPC119631
0.6299 Remote Similarity NPC214067
0.6299 Remote Similarity NPC196246
0.6281 Remote Similarity NPC35448
0.6281 Remote Similarity NPC225060
0.6281 Remote Similarity NPC78701
0.626 Remote Similarity NPC24122
0.625 Remote Similarity NPC1082
0.625 Remote Similarity NPC103387
0.625 Remote Similarity NPC323103
0.625 Remote Similarity NPC305912
0.625 Remote Similarity NPC476003
0.624 Remote Similarity NPC269457
0.6239 Remote Similarity NPC240108
0.6239 Remote Similarity NPC213156
0.6231 Remote Similarity NPC307651
0.622 Remote Similarity NPC17417
0.622 Remote Similarity NPC10251
0.622 Remote Similarity NPC469636
0.621 Remote Similarity NPC234305
0.6202 Remote Similarity NPC270699
0.6202 Remote Similarity NPC82899
0.6198 Remote Similarity NPC276775
0.6198 Remote Similarity NPC249912
0.6198 Remote Similarity NPC92754
0.6198 Remote Similarity NPC270654
0.6182 Remote Similarity NPC299367
0.6179 Remote Similarity NPC42211
0.6172 Remote Similarity NPC93084
0.6172 Remote Similarity NPC251854
0.6148 Remote Similarity NPC475954
0.6142 Remote Similarity NPC56493
0.6111 Remote Similarity NPC472919
0.6107 Remote Similarity NPC153053
0.6098 Remote Similarity NPC325497
0.6098 Remote Similarity NPC118343
0.6094 Remote Similarity NPC474364
0.6094 Remote Similarity NPC83628
0.6094 Remote Similarity NPC469511
0.6094 Remote Similarity NPC265407
0.609 Remote Similarity NPC476014
0.609 Remote Similarity NPC476031
0.608 Remote Similarity NPC89886
0.6071 Remote Similarity NPC121800
0.6071 Remote Similarity NPC195713
0.6066 Remote Similarity NPC325499
0.6063 Remote Similarity NPC119271
0.6053 Remote Similarity NPC472169
0.6048 Remote Similarity NPC70624
0.6047 Remote Similarity NPC174099
0.6033 Remote Similarity NPC130398
0.6031 Remote Similarity NPC128368
0.6017 Remote Similarity NPC9822
0.6015 Remote Similarity NPC216387
0.6 Remote Similarity NPC293424
0.5982 Remote Similarity NPC170484
0.597 Remote Similarity NPC190298
0.5969 Remote Similarity NPC269023
0.5969 Remote Similarity NPC99846
0.5968 Remote Similarity NPC203925
0.5954 Remote Similarity NPC321852
0.5948 Remote Similarity NPC294134
0.594 Remote Similarity NPC474685
0.5938 Remote Similarity NPC472315
0.5938 Remote Similarity NPC472316
0.5938 Remote Similarity NPC37622
0.5938 Remote Similarity NPC30594
0.5938 Remote Similarity NPC474376
0.5938 Remote Similarity NPC475203
0.5923 Remote Similarity NPC273837
0.5906 Remote Similarity NPC269644
0.5906 Remote Similarity NPC85977
0.5906 Remote Similarity NPC31786
0.5903 Remote Similarity NPC23908
0.5896 Remote Similarity NPC149691
0.5891 Remote Similarity NPC277788
0.5887 Remote Similarity NPC476033
0.5882 Remote Similarity NPC254958
0.5882 Remote Similarity NPC254233
0.5882 Remote Similarity NPC291619
0.5878 Remote Similarity NPC474157
0.5878 Remote Similarity NPC260818
0.5877 Remote Similarity NPC165212
0.5873 Remote Similarity NPC188895
0.5873 Remote Similarity NPC45613
0.587 Remote Similarity NPC50872
0.5864 Remote Similarity NPC145990
0.5862 Remote Similarity NPC470794
0.5859 Remote Similarity NPC473855
0.5846 Remote Similarity NPC281604
0.584 Remote Similarity NPC98911
0.584 Remote Similarity NPC472318
0.5839 Remote Similarity NPC4898
0.5833 Remote Similarity NPC185840
0.5833 Remote Similarity NPC105991
0.5833 Remote Similarity NPC84288
0.5827 Remote Similarity NPC91820
0.5827 Remote Similarity NPC82426
0.5826 Remote Similarity NPC106313
0.582 Remote Similarity NPC23453
0.5814 Remote Similarity NPC136962
0.5814 Remote Similarity NPC477251
0.5814 Remote Similarity NPC326447
0.5812 Remote Similarity NPC475710
0.5809 Remote Similarity NPC76308
0.5809 Remote Similarity NPC325295
0.5809 Remote Similarity NPC45794
0.5804 Remote Similarity NPC223807
0.5797 Remote Similarity NPC473243
0.5789 Remote Similarity NPC161611
0.5789 Remote Similarity NPC265002
0.5789 Remote Similarity NPC474176
0.5782 Remote Similarity NPC205915
0.5778 Remote Similarity NPC100353
0.5776 Remote Similarity NPC288903
0.5775 Remote Similarity NPC9180
0.5775 Remote Similarity NPC79608
0.5775 Remote Similarity NPC121272
0.5775 Remote Similarity NPC100402
0.5772 Remote Similarity NPC5472
0.5758 Remote Similarity NPC210089
0.5758 Remote Similarity NPC183700
0.5753 Remote Similarity NPC469499
0.5746 Remote Similarity NPC474363
0.5746 Remote Similarity NPC190212
0.5739 Remote Similarity NPC303245
0.5736 Remote Similarity NPC238115
0.5736 Remote Similarity NPC209632
0.5735 Remote Similarity NPC128249
0.5734 Remote Similarity NPC51292
0.5725 Remote Similarity NPC234956
0.5725 Remote Similarity NPC31274
0.5725 Remote Similarity NPC85493
0.5724 Remote Similarity NPC475508
0.5724 Remote Similarity NPC476748
0.5714 Remote Similarity NPC96625
0.5714 Remote Similarity NPC158282
0.5714 Remote Similarity NPC474314
0.5714 Remote Similarity NPC79496
0.5714 Remote Similarity NPC234376
0.5714 Remote Similarity NPC175393
0.5704 Remote Similarity NPC470008
0.5704 Remote Similarity NPC469509
0.5704 Remote Similarity NPC246166
0.5704 Remote Similarity NPC221275
0.5703 Remote Similarity NPC60679
0.5703 Remote Similarity NPC160382
0.5693 Remote Similarity NPC469574
0.5692 Remote Similarity NPC1065
0.5692 Remote Similarity NPC51174
0.5691 Remote Similarity NPC300455
0.5685 Remote Similarity NPC470278
0.5683 Remote Similarity NPC476183
0.5674 Remote Similarity NPC472703
0.5674 Remote Similarity NPC477151
0.5674 Remote Similarity NPC132518
0.5672 Remote Similarity NPC272524
0.5672 Remote Similarity NPC26615
0.5672 Remote Similarity NPC17693
0.5669 Remote Similarity NPC469481
0.5664 Remote Similarity NPC476599
0.5662 Remote Similarity NPC473507
0.5662 Remote Similarity NPC51345
0.5662 Remote Similarity NPC296526
0.5662 Remote Similarity NPC210531
0.5659 Remote Similarity NPC280616
0.5659 Remote Similarity NPC114594
0.5659 Remote Similarity NPC242913
0.5659 Remote Similarity NPC283546
0.5659 Remote Similarity NPC171831
0.5652 Remote Similarity NPC159916
0.5649 Remote Similarity NPC151530
0.5649 Remote Similarity NPC157473
0.5649 Remote Similarity NPC156648
0.5643 Remote Similarity NPC322569
0.5643 Remote Similarity NPC476281

  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 NPC32356 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
0.75 Intermediate Similarity NPD446 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD1877 Discontinued
0.7073 Intermediate Similarity NPD1279 Clinical (unspecified phase)
0.6857 Remote Similarity NPD7137 Phase 2
0.6829 Remote Similarity NPD5278 Discontinued
0.6797 Remote Similarity NPD2347 Approved
0.6746 Remote Similarity NPD1280 Clinical (unspecified phase)
0.6738 Remote Similarity NPD2862 Discontinued
0.6693 Remote Similarity NPD1246 Approved
0.6439 Remote Similarity NPD1245 Approved
0.6429 Remote Similarity NPD4404 Approved
0.6418 Remote Similarity NPD4480 Approved
0.6387 Remote Similarity NPD3493 Approved
0.6387 Remote Similarity NPD3494 Approved
0.6387 Remote Similarity NPD3492 Approved
0.6364 Remote Similarity NPD41 Approved
0.6364 Remote Similarity NPD5886 Approved
0.635 Remote Similarity NPD4100 Approved
0.635 Remote Similarity NPD4099 Approved
0.6304 Remote Similarity NPD6085 Phase 2
0.6304 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6279 Remote Similarity NPD5277 Phase 2
0.625 Remote Similarity NPD2181 Clinical (unspecified phase)
0.622 Remote Similarity NPD2182 Approved
0.6209 Remote Similarity NPD6813 Clinical (unspecified phase)
0.6207 Remote Similarity NPD5580 Discontinued
0.6159 Remote Similarity NPD6598 Approved
0.6159 Remote Similarity NPD6597 Approved
0.6107 Remote Similarity NPD7976 Clinical (unspecified phase)
0.6098 Remote Similarity NPD1238 Approved
0.6096 Remote Similarity NPD7305 Phase 1
0.6074 Remote Similarity NPD3535 Clinical (unspecified phase)
0.6056 Remote Similarity NPD6966 Discovery
0.6051 Remote Similarity NPD1006 Clinical (unspecified phase)
0.6014 Remote Similarity NPD4232 Approved
0.6 Remote Similarity NPD2202 Clinical (unspecified phase)
0.5988 Remote Similarity NPD5668 Clinical (unspecified phase)
0.5984 Remote Similarity NPD5206 Clinical (unspecified phase)
0.5923 Remote Similarity NPD5236 Approved
0.5923 Remote Similarity NPD5235 Approved
0.5923 Remote Similarity NPD2067 Discontinued
0.5923 Remote Similarity NPD5239 Approved
0.5923 Remote Similarity NPD5240 Approved
0.5923 Remote Similarity NPD5237 Approved
0.5921 Remote Similarity NPD7440 Discontinued
0.5915 Remote Similarity NPD4006 Discontinued
0.5909 Remote Similarity NPD6890 Discontinued
0.5906 Remote Similarity NPD164 Approved
0.5906 Remote Similarity NPD6800 Clinical (unspecified phase)
0.5897 Remote Similarity NPD2512 Phase 3
0.5887 Remote Similarity NPD5926 Approved
0.5864 Remote Similarity NPD3862 Approved
0.5864 Remote Similarity NPD3861 Approved
0.5854 Remote Similarity NPD1989 Approved
0.5833 Remote Similarity NPD3672 Approved
0.5833 Remote Similarity NPD3673 Approved
0.5827 Remote Similarity NPD6647 Phase 2
0.5818 Remote Similarity NPD1194 Discontinued
0.5817 Remote Similarity NPD1979 Approved
0.5814 Remote Similarity NPD6891 Phase 2
0.5814 Remote Similarity NPD3134 Approved
0.5806 Remote Similarity NPD5638 Approved
0.5789 Remote Similarity NPD1978 Approved
0.5778 Remote Similarity NPD4198 Discontinued
0.5772 Remote Similarity NPD9260 Approved
0.5769 Remote Similarity NPD8012 Clinical (unspecified phase)
0.5766 Remote Similarity NPD3798 Phase 3
0.5764 Remote Similarity NPD7055 Discontinued
0.5762 Remote Similarity NPD7974 Phase 3
0.5758 Remote Similarity NPD2201 Approved
0.5753 Remote Similarity NPD4248 Discontinued
0.5735 Remote Similarity NPD3797 Approved
0.5734 Remote Similarity NPD2788 Approved
0.5733 Remote Similarity NPD2531 Phase 2
0.5725 Remote Similarity NPD5585 Approved
0.5725 Remote Similarity NPD4209 Clinical (unspecified phase)
0.5714 Remote Similarity NPD6659 Phase 2
0.5714 Remote Similarity NPD969 Suspended
0.5695 Remote Similarity NPD6005 Phase 3
0.5695 Remote Similarity NPD6002 Phase 3
0.5695 Remote Similarity NPD6006 Clinical (unspecified phase)
0.5695 Remote Similarity NPD6003 Clinical (unspecified phase)
0.5695 Remote Similarity NPD6004 Phase 3
0.5694 Remote Similarity NPD2158 Clinical (unspecified phase)
0.5686 Remote Similarity NPD7835 Discontinued
0.5683 Remote Similarity NPD2345 Approved
0.568 Remote Similarity NPD1672 Phase 2
0.5676 Remote Similarity NPD4340 Discontinued
0.5674 Remote Similarity NPD5702 Clinical (unspecified phase)
0.5674 Remote Similarity NPD6624 Discontinued
0.5672 Remote Similarity NPD5535 Approved
0.5669 Remote Similarity NPD2900 Approved
0.5669 Remote Similarity NPD2901 Approved
0.5669 Remote Similarity NPD3135 Clinical (unspecified phase)
0.5664 Remote Similarity NPD6362 Approved
0.5659 Remote Similarity NPD5909 Discontinued
0.5649 Remote Similarity NPD1358 Approved
0.5641 Remote Similarity NPD1970 Approved
0.5641 Remote Similarity NPD1971 Approved
0.5616 Remote Similarity NPD5952 Clinical (unspecified phase)
0.5605 Remote Similarity NPD6390 Discontinued
0.5605 Remote Similarity NPD5049 Phase 3
0.5603 Remote Similarity NPD6287 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