Structure

Physi-Chem Properties

Molecular Weight:  302.22
Volume:  338.478
LogP:  5.854
LogD:  4.746
LogS:  -5.294
# Rotatable Bonds:  3
TPSA:  33.37
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.725
Synthetic Accessibility Score:  4.193
Fsp3:  0.7
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.731
MDCK Permeability:  1.6290327039314434e-05
Pgp-inhibitor:  0.148
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.962
30% Bioavailability (F30%):  0.148

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.252
Plasma Protein Binding (PPB):  94.52841186523438%
Volume Distribution (VD):  1.743
Pgp-substrate:  2.939380168914795%

ADMET: Metabolism

CYP1A2-inhibitor:  0.226
CYP1A2-substrate:  0.258
CYP2C19-inhibitor:  0.272
CYP2C19-substrate:  0.328
CYP2C9-inhibitor:  0.506
CYP2C9-substrate:  0.612
CYP2D6-inhibitor:  0.284
CYP2D6-substrate:  0.867
CYP3A4-inhibitor:  0.273
CYP3A4-substrate:  0.226

ADMET: Excretion

Clearance (CL):  12.083
Half-life (T1/2):  0.129

ADMET: Toxicity

hERG Blockers:  0.061
Human Hepatotoxicity (H-HT):  0.276
Drug-inuced Liver Injury (DILI):  0.038
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.795
Maximum Recommended Daily Dose:  0.885
Skin Sensitization:  0.539
Carcinogencity:  0.735
Eye Corrosion:  0.304
Eye Irritation:  0.398
Respiratory Toxicity:  0.955

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  Natural Product: NPC35655

Natural Product ID:  NPC35655
Common Name*:   RUXYUBRFOACSMM-ABSDTBQOSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  RUXYUBRFOACSMM-ABSDTBQOSA-N
Standard InCHI:  InChI=1S/C20H30O2/c1-14-6-9-17-19(2,3)10-5-11-20(17,4)16(14)8-7-15-12-18(21)22-13-15/h12,16-17H,1,5-11,13H2,2-4H3/t16-,17-,20+/m0/s1
SMILES:  C=C1CC[C@H]2C(C)(C)CCC[C@]2(C)[C@H]1CCC1=CC(=O)OC1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   24741370
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001538] Diterpene lactones

*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
NPO26456 Jaborosa leucotricha Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[12027740]
NPO25854 Tripterospermum lanceolatum Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[1517742]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[15877880]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[21106458]
NPO25209 Curcuma aromatica Species Zingiberaceae Eukaryota Radix n.a. n.a. PMID[29236488]
NPO41076 Amomum villosum Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[31710213]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota Leaves n.a. Database[FooDB]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25962 Rhamnus cathartica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26113 Strychnos wallichiana Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25264 Cerbera odollam Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25209 Curcuma aromatica Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO26610 Spiraea formosana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25962 Rhamnus cathartica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26113 Strychnos wallichiana Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25264 Cerbera odollam Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25803 Strychnos elaeocarpa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25209 Curcuma aromatica Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25209 Curcuma aromatica Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29093 Homalium longifolium Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25732 Trichilia havanensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17771 Senna didymobotrya Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26357 Trachyrhamphus serratus Species Syngnathidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14283 Ponera metallica Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26481 Astragalus kabadianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26392 Piptadenia colubrina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15693 Guadua angustifolia Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25996 Stenolobium stans n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25264 Cerbera odollam Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25469 Lupinus luteus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23410 Potentilla candicans Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25582 Aquilegia viridiflora Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24733 Celastrus dispermus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26113 Strychnos wallichiana Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26524 Chondria californica Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26554 Hexagonia speciosa Species Carabidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19916 Phenax angustifolius Species Urticaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26816 Clinopodium gracile Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25962 Rhamnus cathartica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25803 Strychnos elaeocarpa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25575 Streptomyces pseudovenezuelae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26306 Pyrobaculum organotrophum Species Thermoproteaceae Archaea n.a. n.a. n.a. Database[UNPD]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25393 Coelogyne flavida Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26743 Lippia adoensis Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24894 Parmelia tinctina Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25086 Viburnum betulifolium Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22353 Lucilia caesar Species Calliphoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24829 Gyrostroma missouriense n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25906 Acacia linarioides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26079 Asterococcus muratae Species Cerococcidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26610 Spiraea formosana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23589 Pecten irradians Species Pectinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7465 Vachellia leucophloea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28819 Veronica liwanensis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26643 Cichorium endivia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13072 Rhamnus formosana Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26175 Spongionella gracilis Species Dictyodendrillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10372 Kiggelaria africana Species Achariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24608 Gaertnera morindoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13051 Perymenium jelskii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25768 Senecio ruwenzoriensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25209 Curcuma aromatica Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26846 Guettarda noumeana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26676 Daphne arisanensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26456 Jaborosa leucotricha Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21639 Prunus mahaleb Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26208 Brombya platynema Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25854 Tripterospermum lanceolatum Species Gentianaceae 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
NPT681 Cell Line PC-12 Rattus norvegicus Activity = 70.24 % PMID[29236488]
NPT681 Cell Line PC-12 Rattus norvegicus Activity = 67.13 % PMID[29236488]
NPT681 Cell Line PC-12 Rattus norvegicus Activity = 72.14 % PMID[29236488]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 18800.0 nM PMID[31710213]
NPT2 Others Unspecified Inhibition = 89.0 % PMID[31710213]
NPT2 Others Unspecified IC50 = 14800.0 nM PMID[31710213]

☑ 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 NPC35655 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 NPC35655 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