Structure

Physi-Chem Properties

Molecular Weight:  1220.62
Volume:  1166.728
LogP:  2.153
LogD:  1.429
LogS:  -3.078
# Rotatable Bonds:  13
TPSA:  412.82
# H-Bond Aceptor:  26
# H-Bond Donor:  15
# Rings:  10
# Heavy Atoms:  26

MedChem Properties

QED Drug-Likeness Score:  0.054
Synthetic Accessibility Score:  7.267
Fsp3:  0.949
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:  -5.957
MDCK Permeability:  0.00031608197605237365
Pgp-inhibitor:  0.036
Pgp-substrate:  0.937
Human Intestinal Absorption (HIA):  0.987
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.057
Plasma Protein Binding (PPB):  60.804073333740234%
Volume Distribution (VD):  -0.209
Pgp-substrate:  19.918745040893555%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.067
CYP2C19-inhibitor:  0.001
CYP2C19-substrate:  0.072
CYP2C9-inhibitor:  0.0
CYP2C9-substrate:  0.003
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.044
CYP3A4-inhibitor:  0.034
CYP3A4-substrate:  0.001

ADMET: Excretion

Clearance (CL):  -0.285
Half-life (T1/2):  0.636

ADMET: Toxicity

hERG Blockers:  0.22
Human Hepatotoxicity (H-HT):  0.11
Drug-inuced Liver Injury (DILI):  0.02
AMES Toxicity:  0.093
Rat Oral Acute Toxicity:  0.138
Maximum Recommended Daily Dose:  0.969
Skin Sensitization:  0.278
Carcinogencity:  0.012
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.907

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

  Natural Product: NPC3853

Natural Product ID:  NPC3853
Common Name*:   PVNXMFDNBHBTQH-WZJLZQBYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  PVNXMFDNBHBTQH-WZJLZQBYSA-N
Standard InCHI:  InChI=1S/C59H96O26/c1-23-34(63)38(67)42(71)49(78-23)83-46-28(20-60)80-48(45(74)41(46)70)77-22-29-37(66)40(69)44(73)51(81-29)85-53(75)59-17-16-54(3,4)18-26(59)25-10-11-31-56(7)14-13-33(55(5,6)30(56)12-15-57(31,8)58(25,9)19-32(59)62)82-52-47(36(65)27(61)21-76-52)84-50-43(72)39(68)35(64)24(2)79-50/h10,23-24,26-52,60-74H,11-22H2,1-9H3/t23-,24-,26-,27-,28+,29+,30-,31+,32+,33-,34-,35-,36-,37+,38+,39+,40-,41+,42+,43+,44+,45+,46+,47+,48+,49-,50-,51-,52-,56-,57+,58+,59+/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=O)[C@]12CCC(C)(C)C[C@H]1C1=CC[C@@H]3[C@@]4(C)CC[C@@H](C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)C[C@H]2O)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O)O)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   21627942
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0001580] Triterpene glycosides
            • [CHEMONTID:0002358] Triterpene 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
NPO22109 Streptomyces clavuligerus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18450406]
NPO22109 Streptomyces clavuligerus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19941870]
NPO22554 Eunicea laciniata Species Plexauridae Eukaryota n.a. Caribbean n.a. PMID[7769391]
NPO22494 Thalictrum rugosum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21909 Alkanna tinctoria Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22494 Thalictrum rugosum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22494 Thalictrum rugosum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22750 Resseliella theobaldi Species Cecidomyiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22494 Thalictrum rugosum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22109 Streptomyces clavuligerus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO27908 Bathynella natans n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO21909 Alkanna tinctoria Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO231 Phanera vahlii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22367 Strychnos hirsuta Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20517 Seseli elatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22554 Eunicea laciniata Species Plexauridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5093 Centaurea hermannii Species Asteraceae 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

☑ 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 NPC3853 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

  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 NPC3853 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

  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