Natural Product: NPC231889

Natural Product IDNPC231889
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 YMKLZOPPOGQOLH-FJSKMCBKSA-N
IUPAC Name n.a.
Synonyms 13-Acetoxysarcocrassolide
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL485787
PubChem CID 21775908
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000147] Macrolides and analogues

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

  Chemical Representations

Standard InCHIKey YMKLZOPPOGQOLH-FJSKMCBKSA-N
Standard InCHI InChI=1S/C22H30O5/c1-13-8-6-10-14(2)19(25-16(4)23)20-17(15(3)21(24)26-20)12-18-22(5,27-18)11-7-9-13/h9-10,17-20H,3,6-8,11-12H2,1-2,4-5H3/b13-9+,14-10+/t17-,18-,19-,20-,22-/m0/s1
SMILES CC(=O)O[C@H]1/C(=C/CC/C(=C/CC[C@]2([C@H](C[C@@H]3[C@@H]1OC(=O)C3=C)O2)C)/C)/C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   374.21 Volume:   394.168
?
Van der Waals volume.
Dense:   0.949 LogP:   3.108
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.084
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.926
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   2.0 Rigid Bonds:   23.0
TPSA:   65.13
?
Topological Polar Surface Area.
 H-Bond Acceptor:   5.0
H-Bond Donor:   0.0 Rings:   3.0
Heavy Atoms:   5.0

MedChem Properties

QED Drug-Likeness Score:   0.3 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   5.0 Fsp3:   0.636
MCE-18:   53.667
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Accepted GSK Rule:   Rejected
Golden Triangle Rule:   Rejected BMS Rule:   1
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.402 Fluc inhibitor:   0.004
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.009
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.039
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.529 Promiscuous compounds:   0.633

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.743 MDCK Permeability:   -4.843
Pgp-inhibitor:   1.0 Pgp-substrate:   0.004
PAMPA:   0.023
?
The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).
 Human Intestinal Absorption (HIA):   0.101
20% Bioavailability (F20%):   0.436 30% Bioavailability (F30%):   0.985
50% Bioavailability (F50%):   0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.001 MRP1:   0.914
Plasma Protein Binding (PPB):   92.012% Volume Distribution (VD):   0.089
Fu: 7.399%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   1.0
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.026
BSEP inhibitor:   1.0

ADMET: Metabolism

CYP1A2-inhibitor:   0.001 CYP1A2-substrate:   0.01
CYP2C19-inhibitor:   0.271 CYP2C19-substrate:   0.001
CYP2C9-inhibitor:   0.045 CYP2C9-substrate:   0.018
CYP2D6-inhibitor:   0.032 CYP2D6-substrate:   0.091
CYP3A4-inhibitor:   0.002 CYP3A4-substrate:   0.809
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.811
HLM stability:   0.633
?
Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):  9.809 Half-life (T1/2):  0.878

ADMET: Toxicity

hERG Blockers:  0.02 hERG Blockers (10um):  0.102
Human Hepatotoxicity (H-HT):  0.655 Drug-induced Liver Injury (DILI):  0.942
AMES Toxicity:  0.615 Rat Oral Acute Toxicity:  0.299
Maximum Recommended Daily Dose:  0.195 Skin Sensitization:  0.995
Carcinogencity:  0.443 Eye Corrosion:  0.085
Eye Irritation:  0.919 Respiratory Toxicity:  0.029
Drug-induced Neurotoxicity:  0.43 Ototoxicity:  0.321
Hematotoxicity:  0.592 Drug-induced Nephrotoxicity:  0.784
Genotoxicity:  0.675 RPMI-8226 Immunitoxicity:  0.095
A549 Cytotoxicity:  0.113 Hek293 Cytotoxicity:  0.201
BCF:   1.415
?
Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].
 IGC50:   4.215
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.964
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   5.468
?
96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[10556916]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10757709]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. formosan soft coral n.a. PMID[11141104]
NPO15773 Ecteinascidia thurstoni Species Perophoridae Eukaryota n.a. Thai n.a. PMID[12088444]
NPO10443 Sloanea zuliaensis Species Elaeocarpaceae Eukaryota n.a. n.a. n.a. PMID[14640532]
NPO16560 Palhinhaea cernua Species Lycopodiaceae Eukaryota n.a. n.a. n.a. PMID[16872152]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[17067165]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[17125220]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. leaf n.a. PMID[17685627]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[19406895]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[19917748]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[20932054]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. Formosan soft coral n.a. PMID[22014827]
NPO25715 Senna siamea Species Fabaceae Eukaryota Stems n.a. n.a. PMID[23078294]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23513740]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[25043228]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[25960261]
NPO16560 Palhinhaea cernua Species Lycopodiaceae Eukaryota n.a. n.a. n.a. PMID[31994397]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[32603106]
NPO14107 Teucrium montanum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[33530639]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. Antarctic n.a. PMID[8882433]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15674 Acanthosyris spinescens Species Cervantesiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26988 Acinos thymoides n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO11762 Agrimonia eupatoria Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14434 Alluaudia humbertii Species Didiereaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13264 Alstonia lanceolifera Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14909 Artemisia caerulescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12217 Buccinum undatum Species Buccinidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6809 Cailliea cinerea n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO13417 Campanula medium Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15428 Cheilanthes tenuifolia Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5127 Cladocroce incurvata Species Chalinidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1655 Corydendrium parasiticum Species Oceaniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13036 Culicinomyces clavisporus Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25278 Cystofilobasidium infirmominiatum Species Cystofilobasidiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12451 Dermocybe cinnabarina Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15037 Echinops spinosissimus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15773 Ecteinascidia thurstoni Species Perophoridae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20404.1 Eruca vesicaria subsp. sativa Subspecies Brassicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15879 Euphorbia nivulia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO639 Formica polyctena Species Formicidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16101 Gleditsia triacanthos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9314 Gouania ulmifolia Species Gobiesocidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5719 Hedyotis lawsoniae Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16740 Helipterum venustum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16774 Hermidium alipes n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO10877 Humboldtia laurifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16301 Ilex macropoda Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11365 Lecidea lithophila Species Lecideaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16453 Lycium cestroides Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2584 Monostroma fuscum Species Monostromataceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16617 Paepalanthus hilairei Species Eriocaulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16560 Palhinhaea cernua Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13577 Pieris formosa Species Ericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO73 Pseudanabaena persicina Species Pseudanabaenaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO16534 Pterocaulon alopecuroides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14591 Rhabdodendron amazonicum Species Rhabdodendraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13733 Saccharopolyspora erythraea Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13931 Selaginella uncinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10443 Sloanea zuliaensis Species Elaeocarpaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7023 Tetracera rosiflora Species Dilleniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14107 Teucrium montanum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12764 Tillandsia fragrans Species Bromeliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15983 Udotea cyathiformis Species Udoteaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16206 Umbilicaria indica Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26508 Uvariopsis tripetala Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16101 Gleditsia triacanthos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13417 Campanula medium Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13931 Selaginella uncinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20404.1 Eruca vesicaria subsp. sativa Subspecies Brassicaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16560 Palhinhaea cernua Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20404.1 Eruca vesicaria subsp. sativa Subspecies Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13931 Selaginella uncinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16101 Gleditsia triacanthos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13577 Pieris formosa Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13417 Campanula medium Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26508 Uvariopsis tripetala Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15983 Udotea cyathiformis Species Udoteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12764 Tillandsia fragrans Species Bromeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15879 Euphorbia nivulia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO73 Pseudanabaena persicina Species Pseudanabaenaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16774 Hermidium alipes n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16560 Palhinhaea cernua Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15674 Acanthosyris spinescens Species Cervantesiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9314 Gouania ulmifolia Species Gobiesocidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15773 Ecteinascidia thurstoni Species Perophoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13036 Culicinomyces clavisporus Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16453 Lycium cestroides Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6809 Cailliea cinerea n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13931 Selaginella uncinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16617 Paepalanthus hilairei Species Eriocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12217 Buccinum undatum Species Buccinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16301 Ilex macropoda Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16740 Helipterum venustum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1655 Corydendrium parasiticum Species Oceaniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13264 Alstonia lanceolifera Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7023 Tetracera rosiflora Species Dilleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16206 Umbilicaria indica Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14107 Teucrium montanum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14909 Artemisia caerulescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11762 Agrimonia eupatoria Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5719 Hedyotis lawsoniae Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16101 Gleditsia triacanthos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12451 Dermocybe cinnabarina Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14434 Alluaudia humbertii Species Didiereaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14591 Rhabdodendron amazonicum Species Rhabdodendraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2584 Monostroma fuscum Species Monostromataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25278 Cystofilobasidium infirmominiatum Species Cystofilobasidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5127 Cladocroce incurvata Species Chalinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20404.1 Eruca vesicaria subsp. sativa Subspecies Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15037 Echinops spinosissimus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26988 Acinos thymoides n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO10443 Sloanea zuliaensis Species Elaeocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16534 Pterocaulon alopecuroides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15428 Cheilanthes tenuifolia Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13733 Saccharopolyspora erythraea Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13417 Campanula medium Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11365 Lecidea lithophila Species Lecideaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13577 Pieris formosa Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10877 Humboldtia laurifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO639 Formica polyctena Species Formicidae 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 Organism Name 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

Molecular-level activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT81 Cell line A549 Homo sapiens ED50 = 4.66 ug ml-1 PMID[11141104]
NPT139 Cell line HT-29 Homo sapiens ED50 = 5.67 ug ml-1 PMID[11141104]
NPT91 Cell line KB Homo sapiens ED50 = 7.39 ug ml-1 PMID[11141104]
NPT168 Cell line P388 Mus musculus ED50 = 0.38 ug ml-1 PMID[11141104]
NPT113 Cell line RAW264.7 Mus musculus Activity = 6.2 % PMID[20144547]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference





 Experimental ADME

Experiment Model Experiment Tissue ADME Type ADME Relation ADME Value ADME Unit Reference





 Experimental Toxicity

Quantitative toxicity

Experiment Model Experiment Organism Toxicity Type Toxicity Relation Toxicity Value Toxicity Unit Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption
Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]


  Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

●  The left chart: Distribution of similarity level between NPC231889 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score Similarity Level Natural Product ID
0.6786 Remote Similarity NPC272814
0.678 Remote Similarity NPC474035
0.678 Remote Similarity NPC81386
0.678 Remote Similarity NPC482125
0.678 Remote Similarity NPC482124
0.623 Remote Similarity NPC51004
0.6071 Remote Similarity NPC256273
0.5806 Remote Similarity NPC329857
0.5806 Remote Similarity NPC469718
0.5758 Remote Similarity NPC476300
0.5714 Remote Similarity NPC30515
0.5593 Remote Similarity NPC605615
0.5517 Remote Similarity NPC38468
0.5517 Remote Similarity NPC192678
0.5517 Remote Similarity NPC319795
0.5517 Remote Similarity NPC50362
0.5517 Remote Similarity NPC488056
0.5517 Remote Similarity NPC605079
0.5397 Remote Similarity NPC476275
0.5385 Remote Similarity NPC14961
0.5385 Remote Similarity NPC270013
0.5286 Remote Similarity NPC476315
0.5238 Remote Similarity NPC471147
0.5238 Remote Similarity NPC605339
0.5231 Remote Similarity NPC476270
0.5224 Remote Similarity NPC81419
0.5224 Remote Similarity NPC179746
0.5179 Remote Similarity NPC223604
0.5156 Remote Similarity NPC212486
0.5077 Remote Similarity NPC157416
0.5077 Remote Similarity NPC475659

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC231889 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.5517 Remote Similarity NPD1733 Clinical (unspecified phase)

Bioactivity similarity

  Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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