Structure

Physi-Chem Properties

Molecular Weight:  190.17
Volume:  222.394
LogP:  4.239
LogD:  4.558
LogS:  -5.073
# Rotatable Bonds:  1
TPSA:  0.0
# H-Bond Aceptor:  0
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  0

MedChem Properties

QED Drug-Likeness Score:  0.55
Synthetic Accessibility Score:  4.3
Fsp3:  0.857
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.469
MDCK Permeability:  8.505211735609919e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.014
30% Bioavailability (F30%):  0.197

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.127
Plasma Protein Binding (PPB):  91.36286163330078%
Volume Distribution (VD):  2.336
Pgp-substrate:  5.222633361816406%

ADMET: Metabolism

CYP1A2-inhibitor:  0.835
CYP1A2-substrate:  0.869
CYP2C19-inhibitor:  0.114
CYP2C19-substrate:  0.942
CYP2C9-inhibitor:  0.043
CYP2C9-substrate:  0.498
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.846
CYP3A4-inhibitor:  0.114
CYP3A4-substrate:  0.441

ADMET: Excretion

Clearance (CL):  13.992
Half-life (T1/2):  0.242

ADMET: Toxicity

hERG Blockers:  0.05
Human Hepatotoxicity (H-HT):  0.355
Drug-inuced Liver Injury (DILI):  0.503
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.08
Maximum Recommended Daily Dose:  0.089
Skin Sensitization:  0.045
Carcinogencity:  0.03
Eye Corrosion:  0.926
Eye Irritation:  0.829
Respiratory Toxicity:  0.452

Download Data

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

  Natural Product: NPC473614

Natural Product ID:  NPC473614
Common Name*:   NEADJUFZWWJHJS-LWENGXMVSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  NEADJUFZWWJHJS-LWENGXMVSA-N
Standard InCHI:  InChI=1S/C14H22/c1-8(2)10-6-7-12-11-5-4-9(3)13(11)14(10)12/h9-14H,1,4-7H2,2-3H3/t9?,10?,11-,12-,13-,14-/m1/s1
SMILES:  CC1CC[C@H]2[C@@H]1[C@H]1[C@@H]2CCC1C(=C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL447205
PubChem CID:   44566865
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001565] Iridoids and derivatives

*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
NPO30160 Cymbastela hooperi Species Axinellidae Eukaryota n.a. n.a. n.a. PMID[19199790]
NPO30160 Cymbastela hooperi Species Axinellidae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO30160 Cymbastela hooperi Species Axinellidae Eukaryota n.a. n.a. n.a. PMID[8759172]

☑ 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
NPT91 Cell Line KB Homo sapiens IC50 > 20.0 ug.mL-1 PMID[465151]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 10.0 ug.mL-1 PMID[465151]

☑ 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 NPC473614 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
0.95 High Similarity NPC474118
0.95 High Similarity NPC51762
0.8571 High Similarity NPC227670
0.8571 High Similarity NPC166362
0.8571 High Similarity NPC141777
0.8182 Intermediate Similarity NPC229403
0.7857 Intermediate Similarity NPC246165
0.7727 Intermediate Similarity NPC90506
0.7727 Intermediate Similarity NPC90803
0.7727 Intermediate Similarity NPC23145
0.75 Intermediate Similarity NPC473912
0.7447 Intermediate Similarity NPC178644
0.7442 Intermediate Similarity NPC227632
0.7442 Intermediate Similarity NPC62086
0.7442 Intermediate Similarity NPC78551
0.7391 Intermediate Similarity NPC49088
0.7347 Intermediate Similarity NPC471681
0.7234 Intermediate Similarity NPC323445
0.7143 Intermediate Similarity NPC200129
0.6957 Remote Similarity NPC109813
0.6957 Remote Similarity NPC60556
0.6786 Remote Similarity NPC162109
0.6667 Remote Similarity NPC15152
0.6522 Remote Similarity NPC103290
0.6415 Remote Similarity NPC127944
0.6383 Remote Similarity NPC177470
0.6383 Remote Similarity NPC193180
0.6383 Remote Similarity NPC190232
0.6383 Remote Similarity NPC105246
0.6327 Remote Similarity NPC241784
0.6327 Remote Similarity NPC114239
0.6327 Remote Similarity NPC13991
0.625 Remote Similarity NPC86538
0.6222 Remote Similarity NPC229262
0.6222 Remote Similarity NPC297643
0.6222 Remote Similarity NPC139717
0.6207 Remote Similarity NPC47840
0.6207 Remote Similarity NPC234264
0.6182 Remote Similarity NPC123194
0.617 Remote Similarity NPC218918
0.617 Remote Similarity NPC120926
0.617 Remote Similarity NPC144023
0.6136 Remote Similarity NPC92224
0.6122 Remote Similarity NPC202189
0.6122 Remote Similarity NPC248411
0.6102 Remote Similarity NPC147524
0.6 Remote Similarity NPC86683
0.6 Remote Similarity NPC190810
0.6 Remote Similarity NPC124112
0.6 Remote Similarity NPC296337
0.6 Remote Similarity NPC76145
0.6 Remote Similarity NPC34764
0.5965 Remote Similarity NPC49575
0.5965 Remote Similarity NPC278550
0.5965 Remote Similarity NPC55004
0.5965 Remote Similarity NPC267626
0.5957 Remote Similarity NPC183670
0.5932 Remote Similarity NPC270042
0.5902 Remote Similarity NPC475704
0.5893 Remote Similarity NPC470893
0.587 Remote Similarity NPC239039
0.587 Remote Similarity NPC266298
0.5862 Remote Similarity NPC469769
0.5862 Remote Similarity NPC472830
0.5778 Remote Similarity NPC282119
0.5769 Remote Similarity NPC124851
0.5763 Remote Similarity NPC309825
0.5763 Remote Similarity NPC184049
0.5763 Remote Similarity NPC5698
0.5763 Remote Similarity NPC99480
0.5763 Remote Similarity NPC469321
0.5763 Remote Similarity NPC52431
0.5763 Remote Similarity NPC310228
0.575 Remote Similarity NPC10183
0.5714 Remote Similarity NPC162309
0.5714 Remote Similarity NPC286752
0.5714 Remote Similarity NPC176171
0.5714 Remote Similarity NPC135650
0.569 Remote Similarity NPC230823
0.5686 Remote Similarity NPC87439
0.5667 Remote Similarity NPC323153
0.5667 Remote Similarity NPC25853
0.5667 Remote Similarity NPC252809
0.566 Remote Similarity NPC22765
0.566 Remote Similarity NPC17518
0.5625 Remote Similarity NPC74885
0.5625 Remote Similarity NPC308522
0.56 Remote Similarity NPC192529

  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 NPC473614 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
0.6383 Remote Similarity NPD1799 Clinical (unspecified phase)
0.6 Remote Similarity NPD319 Phase 1

  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