Structure

Physi-Chem Properties

Molecular Weight:  546.17
Volume:  523.077
LogP:  3.032
LogD:  1.541
LogS:  -4.358
# Rotatable Bonds:  8
TPSA:  207.35
# H-Bond Aceptor:  12
# H-Bond Donor:  7
# Rings:  4
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.157
Synthetic Accessibility Score:  4.388
Fsp3:  0.407
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.164
MDCK Permeability:  1.0777946954476647e-05
Pgp-inhibitor:  0.011
Pgp-substrate:  0.942
Human Intestinal Absorption (HIA):  0.565
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.01
Plasma Protein Binding (PPB):  97.41226959228516%
Volume Distribution (VD):  0.868
Pgp-substrate:  2.944603443145752%

ADMET: Metabolism

CYP1A2-inhibitor:  0.212
CYP1A2-substrate:  0.036
CYP2C19-inhibitor:  0.021
CYP2C19-substrate:  0.057
CYP2C9-inhibitor:  0.285
CYP2C9-substrate:  0.126
CYP2D6-inhibitor:  0.378
CYP2D6-substrate:  0.148
CYP3A4-inhibitor:  0.067
CYP3A4-substrate:  0.021

ADMET: Excretion

Clearance (CL):  1.828
Half-life (T1/2):  0.745

ADMET: Toxicity

hERG Blockers:  0.036
Human Hepatotoxicity (H-HT):  0.179
Drug-inuced Liver Injury (DILI):  0.951
AMES Toxicity:  0.769
Rat Oral Acute Toxicity:  0.013
Maximum Recommended Daily Dose:  0.027
Skin Sensitization:  0.677
Carcinogencity:  0.077
Eye Corrosion:  0.003
Eye Irritation:  0.235
Respiratory Toxicity:  0.109

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  Natural Product: NPC284339

Natural Product ID:  NPC284339
Common Name*:   SHZOHJDZQPQBSW-JTQLQIEISA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  SHZOHJDZQPQBSW-JTQLQIEISA-N
Standard InCHI:  InChI=1S/C17H16O6/c1-21-16-13(19)7-12(15(20)17(16)22-2)10-5-9-3-4-11(18)6-14(9)23-8-10/h3-4,6-7,10,18H,5,8H2,1-2H3/t10-/m0/s1
SMILES:  COC1=C(C(=O)C(=CC1=O)[C@H]1Cc2ccc(cc2OC1)O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   10403457
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0002523] Isoflavanquinones

*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
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. seed n.a. DOI[10.1007/s11418-005-0009-z]
NPO1086 Botrytis cinerea Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. PMID[10691704]
NPO1086 Botrytis cinerea Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. PMID[16378371]
NPO1086 Botrytis cinerea Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. PMID[16643065]
NPO23848 Podophyllum peltatum Species Berberidaceae Eukaryota n.a. n.a. n.a. PMID[16933860]
NPO8025 Aaptos ciliata Species Suberitidae Eukaryota n.a. n.a. n.a. PMID[18257536]
NPO5325 Lobophytum durum Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[19177635]
NPO5325 Lobophytum durum Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[19433363]
NPO2765 Oxytropis falcata Species Fabaceae Eukaryota n.a. Sunan County, Gansu Province, China 2006-JUN PMID[20684529]
NPO5608 Croton gratissimus Species Euphorbiaceae Eukaryota n.a. stem n.a. PMID[22032651]
NPO5608 Croton gratissimus Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[22032651]
NPO2765 Oxytropis falcata Species Fabaceae Eukaryota whole plant Guide County, Qinghai Province, China 2008-AUG PMID[22775441]
NPO8257 Carpha glomerata Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[30219526]
NPO1086 Botrytis cinerea Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. PMID[32705864]
NPO23848 Podophyllum peltatum Species Berberidaceae Eukaryota n.a. root n.a. Database[Article]
NPO784 Sinapis alba Species Brassicaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2340 Caulis spatholobi n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO3344 Bryonia alba Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1473 Xanthorhiza simplicissima Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30663 Millettia dielsiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6859 Eurycoma harmandiana Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23848 Podophyllum peltatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3344 Bryonia alba Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2039 Callerya cinerea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO373 Viburnum erubescens Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23848 Podophyllum peltatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8790 Cyanostegia angustifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2340 Caulis spatholobi n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO1473 Xanthorhiza simplicissima Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2131 Dactylorhiza viridis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6859 Eurycoma harmandiana Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO277 Caulis millettiae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23848 Podophyllum peltatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30663 Millettia dielsiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1473 Xanthorhiza simplicissima Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2765 Oxytropis falcata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8938 Halobacillus litoralis Species Bacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5086 Alternaria macrospora Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3344 Bryonia alba Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1086 Botrytis cinerea Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2039 Callerya cinerea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13474 Euphrasia genargentea Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7032 Marasmiellus troyanus Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO593 Wikstroemia viridiflora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4536 Remirea maritima Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8025 Aaptos ciliata Species Suberitidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21472 Pterolobium hexapetalum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10132 Schizophyllum lobatum Species Schizophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3838 Chrysosporum ovalisporum Species Aphanizomenonaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6807 Ranunculus asiaticus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9998 Abies excelsa Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7418 Eucalyptus resinifera Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5325 Lobophytum durum Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5608 Croton gratissimus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4123 Trididemnum cyanophorum Species Didemnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1293 Streptomyces matensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2670 Maytenus chuchuhuasha Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO373 Viburnum erubescens Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5857 Achlya heterosexualis Species Saprolegniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4901 Arnica mollis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9594 Lysimachia fordiana Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9091 Orthosiphon spicatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2439 Diplopterygium glaucum Species Gleicheniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3151 Solanum lanceolatum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2131 Dactylorhiza viridis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1473 Xanthorhiza simplicissima Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10038.1 Abies pinsapo var. marocana Varieties Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6065 Brassica carinata Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6859 Eurycoma harmandiana Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8790 Cyanostegia angustifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23848 Podophyllum peltatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9737 Ampelocera edentula Species Ulmaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9867 Ixeris debilis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8257 Carpha glomerata Species Cyperaceae 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 NPC284339 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 NPC284339 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