Structure

Physi-Chem Properties

Molecular Weight:  156.03
Volume:  128.996
LogP:  -1.17
LogD:  -0.984
LogS:  -1.316
# Rotatable Bonds:  1
TPSA:  113.65
# H-Bond Aceptor:  7
# H-Bond Donor:  4
# Rings:  1
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.363
Synthetic Accessibility Score:  3.556
Fsp3:  0.0
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:  -5.796
MDCK Permeability:  8.363013876078185e-06
Pgp-inhibitor:  0.001
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.999
Plasma Protein Binding (PPB):  4.911197662353516%
Volume Distribution (VD):  0.546
Pgp-substrate:  75.31423950195312%

ADMET: Metabolism

CYP1A2-inhibitor:  0.031
CYP1A2-substrate:  0.11
CYP2C19-inhibitor:  0.056
CYP2C19-substrate:  0.06
CYP2C9-inhibitor:  0.009
CYP2C9-substrate:  0.651
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.175
CYP3A4-inhibitor:  0.005
CYP3A4-substrate:  0.037

ADMET: Excretion

Clearance (CL):  2.847
Half-life (T1/2):  0.665

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.067
Drug-inuced Liver Injury (DILI):  0.937
AMES Toxicity:  0.195
Rat Oral Acute Toxicity:  0.073
Maximum Recommended Daily Dose:  0.012
Skin Sensitization:  0.774
Carcinogencity:  0.009
Eye Corrosion:  0.003
Eye Irritation:  0.288
Respiratory Toxicity:  0.008

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  Natural Product: NPC264726

Natural Product ID:  NPC264726
Common Name*:   MFAONEQLPARJAO-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  MFAONEQLPARJAO-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C4H4N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h(H4,5,6,7,8,9,10,11)
SMILES:  C1(=NC(=O)N=C1O)NC(=N)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   6852197
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0000013] Amino acids, peptides, and analogues
          • [CHEMONTID:0000347] Amino acids and derivatives
            • [CHEMONTID:0000060] Alpha amino acids 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
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. PMID[10993146]
NPO30067.1 Polyalthia longifolia var. pendula Varieties Annonaceae Eukaryota n.a. n.a. n.a. PMID[11087586]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. Tsukuba, Japan 1998-JUN PMID[12381108]
NPO14814 Aristolochia contorta Species Aristolochiaceae Eukaryota n.a. n.a. n.a. PMID[1431939]
NPO30067.1 Polyalthia longifolia var. pendula Varieties Annonaceae Eukaryota n.a. n.a. n.a. PMID[19860383]
NPO882 Trogopterus xanthipes Species Sciuridae Eukaryota feces n.a. n.a. PMID[20402524]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. leaf n.a. PMID[24197199]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. PMID[24254087]
NPO24833 Dioscorea polystachya Species Dioscoreaceae Eukaryota n.a. bark n.a. PMID[24689699]
NPO30303 Pueraria lobata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25679337]
NPO30067.1 Polyalthia longifolia var. pendula Varieties Annonaceae Eukaryota n.a. n.a. n.a. PMID[25747495]
NPO10680 Cistanche deserticola Species Orobanchaceae Eukaryota n.a. n.a. n.a. PMID[25900014]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. PMID[31861466]
NPO7557 Aristolochia mollissima Species Aristolochiaceae Eukaryota n.a. amniotic fluid n.a. Database[Article]
NPO8589 Triticum aestivum Species Poaceae Eukaryota Oil n.a. n.a. Database[FooDB]
NPO8589 Triticum aestivum Species Poaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO8589 Triticum aestivum Species Poaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO8589 Triticum aestivum Species Poaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO8589 Triticum aestivum Species Poaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO30067.1 Polyalthia longifolia var. pendula Varieties Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24916 Aristolochia debilis Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19228 Rhus typhina Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31003 Moschus sifanicus Species Moschidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30479 Dioscorea batatas Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23020 Aristolochia fangchi Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30303 Pueraria lobata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2341 Fibraurea recisa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14814 Aristolochia contorta Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10680 Cistanche deserticola Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5243 Typha angustata Species Typhaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28397 Wisteria sinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7557 Aristolochia mollissima Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25275 Cynoglossum officinale Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO882 Trogopterus xanthipes Species Sciuridae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO19228 Rhus typhina Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23298 Rhizoma dioscoreae nipponicae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO8111 Rhizoma bolbostemmae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO12246 Moschus chrysogaster Species Moschidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28397 Wisteria sinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4773 Pteromys volans Species Sciuridae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10680 Cistanche deserticola Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO882 Trogopterus xanthipes Species Sciuridae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7557 Aristolochia mollissima Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO463 Moschus berezovskii Species Moschidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24833 Dioscorea polystachya Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23020 Aristolochia fangchi Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25275 Cynoglossum officinale Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14814 Aristolochia contorta Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8707.1 Pueraria montana var. lobata Varieties Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24916 Aristolochia debilis Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2341 Fibraurea recisa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2646 Moschus moschiferus Species Moschidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5243 Typha angustata Species Typhaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30303 Pueraria lobata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO882 Trogopterus xanthipes Species Sciuridae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14814 Aristolochia contorta Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30479 Dioscorea batatas Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4773 Pteromys volans Species Sciuridae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2646 Moschus moschiferus Species Moschidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31003 Moschus sifanicus Species Moschidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7557 Aristolochia mollissima Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28397 Wisteria sinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO463 Moschus berezovskii Species Moschidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19228 Rhus typhina Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24916 Aristolochia debilis Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23020 Aristolochia fangchi Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10680 Cistanche deserticola Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25275 Cynoglossum officinale Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5243 Typha angustata Species Typhaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2341 Fibraurea recisa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8707.1 Pueraria montana var. lobata Varieties Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24833 Dioscorea polystachya Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14814 Aristolochia contorta Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24916 Aristolochia debilis Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10680 Cistanche deserticola Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2646 Moschus moschiferus Species Moschidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO882 Trogopterus xanthipes Species Sciuridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19228 Rhus typhina Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4773 Pteromys volans Species Sciuridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8589 Triticum aestivum Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8707.1 Pueraria montana var. lobata Varieties Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO463 Moschus berezovskii Species Moschidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5243 Typha angustata Species Typhaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24833 Dioscorea polystachya Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28397 Wisteria sinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25275 Cynoglossum officinale Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10680 Cistanche deserticola Species Orobanchaceae 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 NPC264726 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 NPC264726 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