Structure

Physi-Chem Properties

Molecular Weight:  334.21
Volume:  356.058
LogP:  2.831
LogD:  2.437
LogS:  -4.155
# Rotatable Bonds:  1
TPSA:  74.6
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.773
Synthetic Accessibility Score:  4.891
Fsp3:  0.8
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:  -5.054
MDCK Permeability:  1.6685919035808183e-05
Pgp-inhibitor:  0.474
Pgp-substrate:  0.882
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.23
30% Bioavailability (F30%):  0.701

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.964
Plasma Protein Binding (PPB):  68.18037414550781%
Volume Distribution (VD):  0.551
Pgp-substrate:  28.44167709350586%

ADMET: Metabolism

CYP1A2-inhibitor:  0.018
CYP1A2-substrate:  0.62
CYP2C19-inhibitor:  0.044
CYP2C19-substrate:  0.813
CYP2C9-inhibitor:  0.053
CYP2C9-substrate:  0.046
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.078
CYP3A4-inhibitor:  0.379
CYP3A4-substrate:  0.458

ADMET: Excretion

Clearance (CL):  7.546
Half-life (T1/2):  0.075

ADMET: Toxicity

hERG Blockers:  0.018
Human Hepatotoxicity (H-HT):  0.541
Drug-inuced Liver Injury (DILI):  0.038
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.112
Maximum Recommended Daily Dose:  0.355
Skin Sensitization:  0.1
Carcinogencity:  0.183
Eye Corrosion:  0.007
Eye Irritation:  0.025
Respiratory Toxicity:  0.963

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

  Natural Product: NPC303409

Natural Product ID:  NPC303409
Common Name*:   GUBGYTABKSRVRQ-TYAPZPMWSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  GUBGYTABKSRVRQ-TYAPZPMWSA-N
Standard InCHI:  InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8+,9+,10-,11+,12+/m1/s1
SMILES:  C([C@@H]1[C@H]([C@@H]([C@@H]([C@@H](O1)O[C@@H]1[C@@H](CO)O[C@@H]([C@H]([C@H]1O)O)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   5288769
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO7019 Hypericum sampsonii Species Hypericaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.phytochem.2004.08.014]
NPO17509 Gentiana bellidifolia Species Gentianaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4020(01)98434-0]
NPO12113 Aconitum forrestii Species Ranunculaceae Eukaryota n.a. root n.a. DOI[10.1021/np50033a013]
NPO17406 Calophyllum lanigerum Species Calophyllaceae Eukaryota n.a. Sarawak, Malaysia n.a. PMID[11430019]
NPO17406 Calophyllum lanigerum Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[1379639]
NPO12900 Sarcococca hookeriana Species Buxaceae Eukaryota n.a. whole plant n.a. PMID[17827771]
NPO7019 Hypericum sampsonii Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[18038963]
NPO14832 Calocedrus macrolepis Species Cupressaceae Eukaryota n.a. leaf n.a. PMID[18206367]
NPO2421 Picea glauca Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[18636777]
NPO12900 Sarcococca hookeriana Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[18681480]
NPO12900 Sarcococca hookeriana Species Buxaceae Eukaryota n.a. whole plant n.a. PMID[18681480]
NPO19447 Daphniphyllum subverticillatum Species Daphniphyllaceae Eukaryota leaves n.a. n.a. PMID[19739650]
NPO18442 Capsicum baccatum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[21535519]
NPO19581 Marchantia polymorpha Species Marchantiaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO3807 Morinda lucida Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[26048790]
NPO691 Tarchonanthus camphoratus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[29244495]
NPO284 Albizia procera Species Fabaceae Eukaryota Bark n.a. n.a. PMID[30520635]
NPO18682 Piper puberulum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[7623032]
NPO17406 Calophyllum lanigerum Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[8792623]
NPO8770 Euphorbia wallichii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7019 Hypericum sampsonii Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7770 Lactuca laciniata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18682 Piper puberulum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18608 Fagopyrum cymosum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO99 Artemisia porrecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19581 Marchantia polymorpha Species Marchantiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12113 Aconitum forrestii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15880 Microlepia marginata Species Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5588 Bursera tonkinensis Species Burseraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3807 Morinda lucida Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3807 Morinda lucida Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18608 Fagopyrum cymosum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13433 Adenium obesum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16148 Neoboutonia glabrescens Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18682 Piper puberulum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19581 Marchantia polymorpha Species Marchantiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7770 Lactuca laciniata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11662 Solanum virginianum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15880 Microlepia marginata Species Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8770 Euphorbia wallichii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7019 Hypericum sampsonii Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO99 Artemisia porrecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12113 Aconitum forrestii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19432 Millettia pinnata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5588 Bursera tonkinensis Species Burseraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3807 Morinda lucida Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18608 Fagopyrum cymosum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18860 Pelea madagascarica Species Bovidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO99 Artemisia porrecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15597 Calystegia pubescens Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15880 Microlepia marginata Species Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6844 Bulbophyllum protractum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17509 Gentiana bellidifolia Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12283 Macrothelypteris torresiana Species Thelypteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO691 Tarchonanthus camphoratus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19447 Daphniphyllum subverticillatum Species Daphniphyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18361 Mollugo cerviana Species Molluginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22826 Buxus rolfei Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3255 Lampranthus sociorum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3523 Botryllus tyreus Species Styelidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19098 Hypotrachyna quaesita Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17406 Calophyllum lanigerum Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18064 Lycopodium paniculatum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19849 Melilotus officinalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7464 Uruparia lanosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO29287 Alectoria ochroleuca Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8451 Chilo sacchariphagus Species Crambidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19525 Tephrosia bracteolata Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9099 Carissa spinarum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12113 Aconitum forrestii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3807 Morinda lucida Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4952 Pertusaria amara Species Pertusariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2963 Diospyros glaucifolia Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1539 Artemisia giraldii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18442 Capsicum baccatum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12900 Sarcococca hookeriana Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16274 Calonectria lauri Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20860 Lygodium pinnatifidum Species Lygodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4421 Penicillium cyclopium Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2708 Agaricus nebularis Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19314 Albizia schimperana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18940 Selinum papyraceum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18682 Piper puberulum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8920 Balanocarpus heimii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16148 Neoboutonia glabrescens Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19249 Garcinia latissima Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8770 Euphorbia wallichii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5981 Achlys triphylla Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14832 Calocedrus macrolepis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19581 Marchantia polymorpha Species Marchantiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO855 Elymnias thryallis Species Nymphalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13869 Ranunculus bulbosus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13433 Adenium obesum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16249 Dendrobium bicameratum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2421 Picea glauca Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7770 Lactuca laciniata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO565 Poria obliqua Species Coccinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7019 Hypericum sampsonii Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15183 Salvia horminum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18272 Mikania oblongifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19842 Sideritis condensata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3415 Perymenium mendezii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11331 Phellinus tremulae Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5588 Bursera tonkinensis Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18608 Fagopyrum cymosum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18540 Berkheya radula Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17648 Subergorgia hicksoni Species Subergorgiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18778 Paullinia pinnata Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10175 Anaptychia obscura Species Physciaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19432 Millettia pinnata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4117 Nauclea rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3963 Hortonia floribunda Species Monimiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17793 Parkia javanica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11662 Solanum virginianum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16571 Canarium muelleri Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7616 Melanargia galathea Species Nymphalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO284 Albizia procera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27385 Calamus insignis Species Sparidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14266 Borassus flabellifer Species Arecaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3263 Thea sasanqua n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO19722 Tephrosia odorata Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19377 Podocarpus blumei Species Podocarpaceae 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 NPC303409 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 NPC303409 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