Structure

Physi-Chem Properties

Molecular Weight:  238.19
Volume:  259.907
LogP:  2.573
LogD:  2.846
LogS:  -3.246
# Rotatable Bonds:  0
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.681
Synthetic Accessibility Score:  5.577
Fsp3:  1.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.83
MDCK Permeability:  1.3507595213013701e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.291
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.092
30% Bioavailability (F30%):  0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.249
Plasma Protein Binding (PPB):  82.31017303466797%
Volume Distribution (VD):  1.08
Pgp-substrate:  26.33618927001953%

ADMET: Metabolism

CYP1A2-inhibitor:  0.02
CYP1A2-substrate:  0.267
CYP2C19-inhibitor:  0.02
CYP2C19-substrate:  0.849
CYP2C9-inhibitor:  0.052
CYP2C9-substrate:  0.648
CYP2D6-inhibitor:  0.011
CYP2D6-substrate:  0.496
CYP3A4-inhibitor:  0.167
CYP3A4-substrate:  0.156

ADMET: Excretion

Clearance (CL):  7.125
Half-life (T1/2):  0.513

ADMET: Toxicity

hERG Blockers:  0.03
Human Hepatotoxicity (H-HT):  0.309
Drug-inuced Liver Injury (DILI):  0.02
AMES Toxicity:  0.017
Rat Oral Acute Toxicity:  0.957
Maximum Recommended Daily Dose:  0.92
Skin Sensitization:  0.452
Carcinogencity:  0.157
Eye Corrosion:  0.264
Eye Irritation:  0.538
Respiratory Toxicity:  0.965

Download Data

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

  Natural Product: NPC142167

Natural Product ID:  NPC142167
Common Name*:   BWXJQHJHGMZLBT-AMVBZWJASA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  BWXJQHJHGMZLBT-AMVBZWJASA-N
Standard InCHI:  InChI=1S/C15H26O2/c1-13(2)8-12(17)15-7-5-11(16)14(3,9-15)6-4-10(13)15/h10-12,16-17H,4-9H2,1-3H3/t10-,11-,12+,14-,15+/m1/s1
SMILES:  CC1(C)C[C@@H]([C@@]23CC[C@H]([C@](C)(CC[C@H]13)C2)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO17119 Dalea versicolor Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[15043439]
NPO18606 Achyrocline bogotensis Species Asteraceae Eukaryota n.a. Colombian n.a. PMID[15844937]
NPO3291 Cynanchum auriculatum Species Apocynaceae Eukaryota n.a. root n.a. PMID[18401845]
NPO17362 Alstonia yunnanensis Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[19775092]
NPO18055 Isodon adenolomus Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[21534539]
NPO18055 Isodon adenolomus Species Lamiaceae Eukaryota aerial parts Shangrila, Yunnan Province, China 2008-AUG PMID[21534539]
NPO17376 Bacillus amyloliquefaciens Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[23265519]
NPO17376 Bacillus amyloliquefaciens Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[24698790]
NPO17376 Bacillus amyloliquefaciens Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[27934031]
NPO12148.2 Acer pictum subsp. okamotoanum Subspecies Sapindaceae Eukaryota n.a. n.a. n.a. PMID[9461665]
NPO17362 Alstonia yunnanensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18356 Stachys tuberifera Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3291 Cynanchum auriculatum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18435 Tylophora atrofolliculata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18435 Tylophora atrofolliculata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18356 Stachys tuberifera Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3291 Cynanchum auriculatum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17362 Alstonia yunnanensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17362 Alstonia yunnanensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3291 Cynanchum auriculatum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18435 Tylophora atrofolliculata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4984 Salvia cana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16803 Libanothamnus occultus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19638 Scutellaria albida Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18606 Achyrocline bogotensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4230 Protoparmeliopsis peltata Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19777 Pholiota adiposa Species Strophariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19522 Arthropsis truncata Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17376 Bacillus amyloliquefaciens Species Bacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26131 Cliona chilensis Species Clionaidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10852 Felimare midatlantica Species Chromodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1826 Teucrium barbeyanum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19311 Dasymaschalon blumei Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18055 Isodon adenolomus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3291 Cynanchum auriculatum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12148.2 Acer pictum subsp. okamotoanum Subspecies Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17783 Sideritis cystosiphon Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17119 Dalea versicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17362 Alstonia yunnanensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17911 Blepharisma japonicum Species Blepharismidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13832 Aspilia hispida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16997 Talaromyces aculeatus Species Trichocomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15497 Caria ino Species Riodinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17643 Penicillium pedemontanum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14262 Eucalyptus polyanthemos Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16990 Verbesina virgata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2377 Cetraria ciliaris Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13974 Hygrophorus pustulatus Species Hygrophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19778 Streptomyces flaveus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18356 Stachys tuberifera Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13414 Senecio fuertesii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16567 Doriopsilla areolata Species Dendrodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19580 Chamaemelum fuscatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19118 Hippeastrum vittatum Species Amaryllidaceae 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 NPC142167 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 NPC142167 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