Structure

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Physi-Chem Properties

Molecular Weight:  324.26
Volume:  366.29
LogP:  5.247
LogD:  5.17
LogS:  -5.158
# Rotatable Bonds:  0
TPSA:  8.72
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.505
Synthetic Accessibility Score:  5.57
Fsp3:  0.909
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.717
MDCK Permeability:  7.266795000759885e-05
Pgp-inhibitor:  0.997
Pgp-substrate:  0.833
Human Intestinal Absorption (HIA):  0.051
20% Bioavailability (F20%):  0.713
30% Bioavailability (F30%):  0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.935
Plasma Protein Binding (PPB):  70.70086669921875%
Volume Distribution (VD):  0.926
Pgp-substrate:  16.356416702270508%

ADMET: Metabolism

CYP1A2-inhibitor:  0.124
CYP1A2-substrate:  0.967
CYP2C19-inhibitor:  0.01
CYP2C19-substrate:  0.514
CYP2C9-inhibitor:  0.009
CYP2C9-substrate:  0.038
CYP2D6-inhibitor:  0.059
CYP2D6-substrate:  0.037
CYP3A4-inhibitor:  0.637
CYP3A4-substrate:  0.303

ADMET: Excretion

Clearance (CL):  12.968
Half-life (T1/2):  0.717

ADMET: Toxicity

hERG Blockers:  0.264
Human Hepatotoxicity (H-HT):  0.594
Drug-inuced Liver Injury (DILI):  0.888
AMES Toxicity:  0.021
Rat Oral Acute Toxicity:  0.973
Maximum Recommended Daily Dose:  0.92
Skin Sensitization:  0.928
Carcinogencity:  0.163
Eye Corrosion:  0.992
Eye Irritation:  0.768
Respiratory Toxicity:  0.986

Download Data

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

  Natural Product: NPC212905

Natural Product ID:  NPC212905
Common Name*:   Diisocyanoadociane
IUPAC Name:   (2R,3R,3aS,5aS,6S,8aR,9S,10aS,10bS,10cS)-3,6-diisocyano-2,3,6,9-tetramethyl-1,2,3a,4,5,5a,7,8,8a,9,10,10a,10b,10c-tetradecahydropyrene
Synonyms:   Diisocyanoadociane
Standard InCHIKey:  XLVAONKBFLGZSE-OXEUSEQRSA-N
Standard InCHI:  InChI=1S/C22H32N2/c1-13-11-15-12-14(2)22(4,24-6)18-8-7-17-20(19(15)18)16(13)9-10-21(17,3)23-5/h13-20H,7-12H2,1-4H3/t13-,14+,15-,16+,17-,18-,19+,20+,21-,22+/m0/s1
SMILES:  C[C@H]1C[C@H]2C[C@@H](C)[C@](C)([C@H]3CC[C@H]4[C@@H]([C@@H]1CC[C@]4(C)[N+]#[C-])[C@H]23)[N+]#[C-]
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL353048
PubChem CID:   194103
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0003398] Amphilectane, neoamphilectane, cycloamphilectane, and adociane diterpenoids

*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

☑ 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

☑ 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

☑ 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 NPC212905 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

  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 NPC212905 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

  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