Structure

Physi-Chem Properties

Molecular Weight:  174.12
Volume:  193.147
LogP:  1.943
LogD:  1.531
LogS:  -1.178
# Rotatable Bonds:  2
TPSA:  19.03
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.739
Synthetic Accessibility Score:  1.837
Fsp3:  0.273
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.44
MDCK Permeability:  1.1245942005189136e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.009
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.988
Plasma Protein Binding (PPB):  26.952922821044922%
Volume Distribution (VD):  2.704
Pgp-substrate:  67.87498474121094%

ADMET: Metabolism

CYP1A2-inhibitor:  0.446
CYP1A2-substrate:  0.95
CYP2C19-inhibitor:  0.049
CYP2C19-substrate:  0.936
CYP2C9-inhibitor:  0.011
CYP2C9-substrate:  0.648
CYP2D6-inhibitor:  0.963
CYP2D6-substrate:  0.93
CYP3A4-inhibitor:  0.012
CYP3A4-substrate:  0.291

ADMET: Excretion

Clearance (CL):  10.459
Half-life (T1/2):  0.76

ADMET: Toxicity

hERG Blockers:  0.082
Human Hepatotoxicity (H-HT):  0.433
Drug-inuced Liver Injury (DILI):  0.822
AMES Toxicity:  0.038
Rat Oral Acute Toxicity:  0.944
Maximum Recommended Daily Dose:  0.869
Skin Sensitization:  0.862
Carcinogencity:  0.059
Eye Corrosion:  0.757
Eye Irritation:  0.382
Respiratory Toxicity:  0.98

Download Data

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General Info & Identifiers & Properties  
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  Natural Product: NPC52197

Natural Product ID:  NPC52197
Common Name*:   OCDGBSUVYYVKQZ-UHFFFAOYSA-O
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  OCDGBSUVYYVKQZ-UHFFFAOYSA-O
Standard InCHI:  InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3/p+1
SMILES:  CN(C)CC1=C[NH2+]c2ccccc12
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   3480616
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0002497] Indoles
          • [CHEMONTID:0004196] 3-alkylindoles

*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
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota Fruits n.a. n.a. PMID[11141122]
NPO25611 Smilax china Species Smilacaceae Eukaryota stems n.a. n.a. PMID[16252910]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. PMID[18270436]
NPO28946 Acer rubrum Species Sapindaceae Eukaryota Stems n.a. n.a. PMID[22079755]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. PMID[23793896]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. seed n.a. PMID[24967651]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO28946 Acer rubrum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14297 Dioscorea gracillima Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9436 Dioscorea parviflora Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18881 Loropetalum chinense Species Hamamelidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18498 Arundo donax Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30073 Costus speciosus Species Costaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19287 Phalaris arundinacea Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27509 Dioscorea zingiberensis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23313 Dioscorea althaeoides Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17650 Dioscorea septemloba Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4863 Dioscorea futschauensis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21943 Acer saccharinum Species Aceraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27509 Dioscorea zingiberensis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4863 Dioscorea futschauensis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18881 Loropetalum chinense Species Hamamelidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19287 Phalaris arundinacea Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28946 Acer rubrum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21651 Cheilocostus speciosus Species Costaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23313 Dioscorea althaeoides Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18498 Arundo donax Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21943 Acer saccharinum Species Aceraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14297 Dioscorea gracillima Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17650 Dioscorea septemloba Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9436 Dioscorea parviflora Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17650 Dioscorea septemloba Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30073 Costus speciosus Species Costaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18498 Arundo donax Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4863 Dioscorea futschauensis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14297 Dioscorea gracillima Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18881 Loropetalum chinense Species Hamamelidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19287 Phalaris arundinacea Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27509 Dioscorea zingiberensis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21943 Acer saccharinum Species Aceraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28946 Acer rubrum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23313 Dioscorea althaeoides Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17650 Dioscorea septemloba Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4863 Dioscorea futschauensis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21943 Acer saccharinum Species Aceraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19287 Phalaris arundinacea Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27509 Dioscorea zingiberensis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18881 Loropetalum chinense Species Hamamelidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4863 Dioscorea futschauensis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18498 Arundo donax Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14297 Dioscorea gracillima Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28946 Acer rubrum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7395 Tribulus terrestris Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21651 Cheilocostus speciosus Species Costaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23313 Dioscorea althaeoides Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17650 Dioscorea septemloba Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22132 Hordeum vulgare Species Poaceae 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 NPC52197 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 NPC52197 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