Structure

Physi-Chem Properties

Molecular Weight:  578.14
Volume:  555.862
LogP:  3.549
LogD:  2.529
LogS:  -4.497
# Rotatable Bonds:  8
TPSA:  196.35
# H-Bond Aceptor:  12
# H-Bond Donor:  6
# Rings:  5
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.138
Synthetic Accessibility Score:  4.127
Fsp3:  0.2
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.296
MDCK Permeability:  1.5503990653087385e-05
Pgp-inhibitor:  0.015
Pgp-substrate:  0.866
Human Intestinal Absorption (HIA):  0.549
20% Bioavailability (F20%):  0.693
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.011
Plasma Protein Binding (PPB):  100.44757843017578%
Volume Distribution (VD):  0.64
Pgp-substrate:  2.3091769218444824%

ADMET: Metabolism

CYP1A2-inhibitor:  0.655
CYP1A2-substrate:  0.024
CYP2C19-inhibitor:  0.306
CYP2C19-substrate:  0.052
CYP2C9-inhibitor:  0.548
CYP2C9-substrate:  0.866
CYP2D6-inhibitor:  0.781
CYP2D6-substrate:  0.309
CYP3A4-inhibitor:  0.461
CYP3A4-substrate:  0.082

ADMET: Excretion

Clearance (CL):  3.816
Half-life (T1/2):  0.574

ADMET: Toxicity

hERG Blockers:  0.352
Human Hepatotoxicity (H-HT):  0.421
Drug-inuced Liver Injury (DILI):  0.95
AMES Toxicity:  0.656
Rat Oral Acute Toxicity:  0.03
Maximum Recommended Daily Dose:  0.053
Skin Sensitization:  0.951
Carcinogencity:  0.088
Eye Corrosion:  0.003
Eye Irritation:  0.043
Respiratory Toxicity:  0.035

Download Data

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

  Natural Product: NPC156851

Natural Product ID:  NPC156851
Common Name*:   UTUISHMYVAZILQ-NBJODKRESA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  UTUISHMYVAZILQ-NBJODKRESA-N
Standard InCHI:  InChI=1S/C30H26O12/c31-14-24-29(42-25(36)10-3-15-1-6-17(32)7-2-15)27(37)28(38)30(41-24)39-19-11-20(34)26-21(35)13-22(40-23(26)12-19)16-4-8-18(33)9-5-16/h1-13,24,27-34,37-38H,14H2/b10-3-/t24-,27-,28-,29-,30-/m1/s1
SMILES:  c1cc(ccc1/C=CC(=O)O[C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)Oc1cc(c2c(=O)cc(c3ccc(cc3)O)oc2c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   16109840
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0003533] Flavonoid-7-O-glycosides

*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
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[15678383]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[16045947]
NPO8764 Laurencia decumbens Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[17711344]
NPO8653 Leuconostoc mesenteroides Species Leuconostocaceae Bacteria n.a. n.a. n.a. PMID[19025748]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. PMID[19245240]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. stem n.a. PMID[20188156]
NPO3123 Anthemis cretica Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[22351977]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. Malaysian n.a. PMID[7506311]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3123 Anthemis cretica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28741 Afrocarpus gracilior Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6766 Antiphiona pinnatisecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9567 Enicosanthum cupulare Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8653 Leuconostoc mesenteroides Species Leuconostocaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10991 Maackia tashiroi Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8764 Laurencia decumbens Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2012 Turnera diffusa Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9136 Pseudocyclosorus subochthodes Species Thelypteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28741 Afrocarpus gracilior Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3123 Anthemis cretica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2495 Agave xylonacantha Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19826 Helicoverpa armigera Species 0ctuidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26103 Streptomyces bobili Species Streptomycetaceae Bacteria 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 NPC156851 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 NPC156851 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