Structure

Physi-Chem Properties

Molecular Weight:  190.11
Volume:  196.017
LogP:  0.421
LogD:  0.701
LogS:  0.572
# Rotatable Bonds:  0
TPSA:  34.03
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.648
Synthetic Accessibility Score:  4.046
Fsp3:  0.545
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:  -5.177
MDCK Permeability:  3.79873040401435e-06
Pgp-inhibitor:  0.002
Pgp-substrate:  0.025
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.028
30% Bioavailability (F30%):  0.812

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.948
Plasma Protein Binding (PPB):  15.949216842651367%
Volume Distribution (VD):  1.951
Pgp-substrate:  81.4118423461914%

ADMET: Metabolism

CYP1A2-inhibitor:  0.102
CYP1A2-substrate:  0.254
CYP2C19-inhibitor:  0.044
CYP2C19-substrate:  0.704
CYP2C9-inhibitor:  0.01
CYP2C9-substrate:  0.08
CYP2D6-inhibitor:  0.722
CYP2D6-substrate:  0.591
CYP3A4-inhibitor:  0.075
CYP3A4-substrate:  0.322

ADMET: Excretion

Clearance (CL):  6.318
Half-life (T1/2):  0.3

ADMET: Toxicity

hERG Blockers:  0.235
Human Hepatotoxicity (H-HT):  0.617
Drug-inuced Liver Injury (DILI):  0.134
AMES Toxicity:  0.825
Rat Oral Acute Toxicity:  0.889
Maximum Recommended Daily Dose:  0.958
Skin Sensitization:  0.265
Carcinogencity:  0.581
Eye Corrosion:  0.006
Eye Irritation:  0.056
Respiratory Toxicity:  0.833

Download Data

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

  Natural Product: NPC132858

Natural Product ID:  NPC132858
Common Name*:   ANJTVLIZGCUXLD-RKDXNWHRSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  ANJTVLIZGCUXLD-RKDXNWHRSA-N
Standard InCHI:  InChI=1S/C11H14N2O/c14-11-3-1-2-10-9-4-8(5-12-6-9)7-13(10)11/h1-3,8-9,12H,4-7H2/t8-,9-/m1/s1
SMILES:  O=c1cccc2n1C[C@H]1CNC[C@H]2C1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2374256
PubChem CID:   1549781
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002719] Lupin alkaloids
        • [CHEMONTID:0002722] Cytisine 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
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10654410]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[10843587]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[15568770]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16392664]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16933887]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota roots Hualien Hsien, Taiwan 2003-JUL PMID[16933887]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[17951038]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[18175961]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24295087]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[27575476]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[30298740]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[9868163]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. Database[Article]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19231 Sophora flavescens Species Fabaceae 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
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 31622.8 nM PMID[502120]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 28183.8 nM PMID[502121]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 31622.8 nM PMID[502121]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 31622.8 nM PMID[502120]
NPT63 Individual Protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 89125.1 nM PMID[502122]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 100000.0 nM PMID[502122]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 46989.41 nM PMID[502123]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[502123]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 316.2 nM PMID[502122]
NPT161 Individual Protein Rap guanine nucleotide exchange factor 4 Homo sapiens Potency n.a. 3162.3 nM PMID[502122]
NPT2 Others Unspecified Potency = 163.6 nM PMID[502122]
NPT533 Protein-Protein Interaction Runt-related transcription factor 1/Core-binding factor subunit beta Homo sapiens Potency n.a. 2238.7 nM PMID[502121]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 16.5 nM PMID[502122]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 4213.5 nM PMID[502124]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 149.5 nM PMID[502124]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 1.5 nM PMID[502124]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 7492.9 nM PMID[502124]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 4.51 % PMID[502125]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae Inhibition = 2.72 % PMID[502125]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 4.01 % PMID[502125]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans Inhibition = -10.24 % PMID[502125]
NPT2922 Organism Staphylococcus aureus subsp. aureus Staphylococcus aureus subsp. aureus Inhibition = 0.43 % PMID[502125]
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii Inhibition = -9.28 % PMID[502125]
NPT20 Organism Candida albicans Candida albicans Inhibition = 0.25 % PMID[502125]

☑ 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 NPC132858 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
1.0 High Similarity NPC267203
1.0 High Similarity NPC77890
0.9189 High Similarity NPC63284
0.9067 High Similarity NPC320667
0.9067 High Similarity NPC214125
0.8947 High Similarity NPC244256
0.8947 High Similarity NPC86452
0.8193 Intermediate Similarity NPC143344
0.8193 Intermediate Similarity NPC135639
0.8193 Intermediate Similarity NPC234822
0.8193 Intermediate Similarity NPC78058
0.8193 Intermediate Similarity NPC61321
0.8 Intermediate Similarity NPC25513
0.759 Intermediate Similarity NPC120699
0.759 Intermediate Similarity NPC127430
0.7159 Intermediate Similarity NPC207048
0.7143 Intermediate Similarity NPC308050
0.6753 Remote Similarity NPC42477
0.6667 Remote Similarity NPC477460
0.6667 Remote Similarity NPC76869
0.6632 Remote Similarity NPC145707
0.6591 Remote Similarity NPC268580
0.6538 Remote Similarity NPC470738
0.65 Remote Similarity NPC206660
0.63 Remote Similarity NPC91036
0.6237 Remote Similarity NPC116881
0.6237 Remote Similarity NPC57163
0.6222 Remote Similarity NPC472194
0.6117 Remote Similarity NPC100810
0.6117 Remote Similarity NPC144714
0.6111 Remote Similarity NPC28529
0.6105 Remote Similarity NPC476141
0.6076 Remote Similarity NPC385
0.6049 Remote Similarity NPC477461
0.6049 Remote Similarity NPC477459
0.6 Remote Similarity NPC133923
0.5888 Remote Similarity NPC472856
0.5854 Remote Similarity NPC252684
0.5851 Remote Similarity NPC255430
0.5778 Remote Similarity NPC34672
0.5766 Remote Similarity NPC143173
0.5714 Remote Similarity NPC17497
0.5714 Remote Similarity NPC476559
0.5714 Remote Similarity NPC305602

  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 NPC132858 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
1.0 High Similarity NPD529 Approved
0.6353 Remote Similarity NPD816 Approved
0.6353 Remote Similarity NPD815 Approved
0.5849 Remote Similarity NPD2905 Discontinued
0.5818 Remote Similarity NPD4063 Clinical (unspecified phase)
0.5726 Remote Similarity NPD1306 Clinical (unspecified phase)
0.57 Remote Similarity NPD1691 Clinical (unspecified phase)

  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