Natural Product: NPC179798

Natural Product IDNPC179798
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 [(5R,5As,9As,9Bs)-9B-Hydroxy-6,6,9A-Trimethyl-1-Oxo-3,5,5A,7,8,9-Hexahydrobenzo[E][2]Benzofuran-5-Yl] (2E,4E,6E)-Octa-2,4,6-Trienoate
IUPAC Name [(5R,5aS,9aS,9bS)-9b-hydroxy-6,6,9a-trimethyl-1-oxo-3,5,5a,7,8,9-hexahydrobenzo[e][2]benzofuran-5-yl] (2E,4E,6E)-octa-2,4,6-trienoate
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1078730
PubChem CID 10407821
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001634] Naphthofurans

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 DPTZOOXIEWHODB-XLDMSTKGSA-N
Standard InCHI InChI=1S/C23H30O5/c1-5-6-7-8-9-11-18(24)28-17-14-16-15-27-20(25)23(16,26)22(4)13-10-12-21(2,3)19(17)22/h5-9,11,14,17,19,26H,10,12-13,15H2,1-4H3/b6-5+,8-7+,11-9+/t17-,19+,22+,23+/m1/s1
SMILES C/C=C/C=C/C=C/C(=O)O[C@@H]1C=C2COC(=O)[C@@]2([C@@]2(C)CCCC(C)(C)[C@H]12)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   386.21 Volume:   408.827
?
Van der Waals volume.
Dense:   0.945 LogP:   2.466
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.536
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.219
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   5.0 Rigid Bonds:   20.0
TPSA:   72.83
?
Topological Polar Surface Area.
 H-Bond Acceptor:   5.0
H-Bond Donor:   1.0 Rings:   3.0
Heavy Atoms:   5.0

MedChem Properties

QED Drug-Likeness Score:   0.346 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   4.734 Fsp3:   0.565
MCE-18:   57.5
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Rejected GSK Rule:   Rejected
Golden Triangle Rule:   Rejected BMS Rule:   1
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.668 Fluc inhibitor:   0.421
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.122
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.207
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.473 Promiscuous compounds:   0.331

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.032 MDCK Permeability:   -4.795
Pgp-inhibitor:   0.618 Pgp-substrate:   0.471
PAMPA:   0.958
?
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):   0.028
20% Bioavailability (F20%):   0.968 30% Bioavailability (F30%):   0.989
50% Bioavailability (F50%):   0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.01 MRP1:   0.646
Plasma Protein Binding (PPB):   98.626% Volume Distribution (VD):   -0.196
Fu: 1.199%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   1.0
OATP1B3 inhibitor:   0.998 BCRP inhibitor:   0.001
BSEP inhibitor:   1.0

ADMET: Metabolism

CYP1A2-inhibitor:   0.068 CYP1A2-substrate:   1.0
CYP2C19-inhibitor:   0.004 CYP2C19-substrate:   0.999
CYP2C9-inhibitor:   0.002 CYP2C9-substrate:   0.067
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.897
CYP3A4-inhibitor:   0.68 CYP3A4-substrate:   1.0
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.999
?
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):  5.629 Half-life (T1/2):  1.157

ADMET: Toxicity

hERG Blockers:  0.032 hERG Blockers (10um):  0.223
Human Hepatotoxicity (H-HT):  0.791 Drug-induced Liver Injury (DILI):  0.629
AMES Toxicity:  0.894 Rat Oral Acute Toxicity:  0.582
Maximum Recommended Daily Dose:  0.844 Skin Sensitization:  0.998
Carcinogencity:  0.975 Eye Corrosion:  0.034
Eye Irritation:  0.756 Respiratory Toxicity:  0.361
Drug-induced Neurotoxicity:  0.304 Ototoxicity:  0.383
Hematotoxicity:  0.555 Drug-induced Nephrotoxicity:  0.961
Genotoxicity:  0.981 RPMI-8226 Immunitoxicity:  0.138
A549 Cytotoxicity:  0.203 Hek293 Cytotoxicity:  0.446
BCF:   1.699
?
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:   4.393
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.908
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   5.467
?
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
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. twig n.a. DOI[10.1021/np50063a031]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. stem n.a. DOI[10.1021/np50063a031]
NPO16456 Mirabilis jalapa Species Nyctaginaceae Eukaryota n.a. n.a. n.a. PMID[11277746]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[15165134]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. twig n.a. PMID[16254827]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. stem n.a. PMID[16254827]
NPO16566 Cinnamosma madagascariensis Species Canellaceae Eukaryota n.a. n.a. n.a. PMID[18179176]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19769341]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota Suberites domuncula n.a. n.a. PMID[19778087]
NPO17999 Sonneratia alba Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[19835393]
NPO22097 Plakinastrella clathrata Species Plakinidae Eukaryota n.a. n.a. n.a. PMID[21261297]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21348461]
NPO16812 Ajuga bracteosa Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[21539300]
NPO9189 Streptomyces atratus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21868221]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[22316191]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24033077]
NPO5119 Pseudomonas chlororaphis Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[25679537]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25706180]
NPO5119 Pseudomonas chlororaphis Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[25901993]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[2778454]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[29286660]
NPO15599 Daldinia concentrica Species n.a. Eukaryota Fruiting Bodies n.a. n.a. PMID[29715021]
NPO16456 Mirabilis jalapa Species Nyctaginaceae Eukaryota n.a. n.a. n.a. PMID[37687143]
NPO16455 Xylopia aethiopica Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[8158166]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15919 Streptomyces caelestis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO9189 Streptomyces atratus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO17844 Agaricus integer Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14813 Agaricus silvaticus Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16812 Ajuga bracteosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17921 Allium monspessulanum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17602 Arbutus menziesii Species Ericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15004 Artemisia taurica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4507 Bruguiera gymnorhiza Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25550 Buchenavia tetraphylla Species Combretaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17375 Ceramium botryocarpum Species Ceramiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16923 Cereus chrysacanthus Species Sagartiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16052 Chromodoris obsoleta Species Chromodorididae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16566 Cinnamosma madagascariensis Species Canellaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17071 Coeloseira pacifica Species Champiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15599 Daldinia concentrica Species n.a. Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4336 Echiochilon pauciflorum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16695 Fumaria kraliki Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17218 Helichrysum nudifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9951 Hyella caespitosa Species Hyellaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO15748 Hypoxis nyasica Species Hypoxidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO84 Isoberlinia angolensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18073 Justicia trinervia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7905 Lepista irina Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17339 Macaranga sinensis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16456 Mirabilis jalapa Species Nyctaginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8010 Otostegia fruticosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13789 Paranephelius uniflorus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28868 Pardachirus pavoninus Species Soleidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14575 Periploca forrestii Species Cosmopterigidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14002 Petalostemon purpureum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22097 Plakinastrella clathrata Species Plakinidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11408 Podocarpus amarus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16329 Potebniamyces gallicola Species Phacidiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5119 Pseudomonas chlororaphis Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO10770 Ptilota pectinata Species Ceramiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21437 Rhododendron aureum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13013 Saccharothrix mutabilis Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO17304 Sipunculus nudus Species Sipunculidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17999 Sonneratia alba Species Lythraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26788 Sophora viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28821 Stichopus horrens Species Stichopodidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2155 Tephroseris integrifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11760 Teucrium orientale Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2550 Trichoderma citrinum Species Hypocreaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28319 Ulva prolifera Species Ulvaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16215 Umbilicaria cinereorufescens Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15545 Veltheimia viridifolia Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16455 Xylopia aethiopica Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16456 Mirabilis jalapa Species Nyctaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26788 Sophora viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15004 Artemisia taurica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14575 Periploca forrestii Species Cosmopterigidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26788 Sophora viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16456 Mirabilis jalapa Species Nyctaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4507 Bruguiera gymnorhiza Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8010 Otostegia fruticosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15004 Artemisia taurica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14575 Periploca forrestii Species Cosmopterigidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21437 Rhododendron aureum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11760 Teucrium orientale Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15004 Artemisia taurica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15599 Daldinia concentrica Species n.a. Eukaryota n.a. n.a. n.a. Database[Title]
NPO5119 Pseudomonas chlororaphis Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO14813 Agaricus silvaticus Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28821 Stichopus horrens Species Stichopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13013 Saccharothrix mutabilis Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO7905 Lepista irina Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11760 Teucrium orientale Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO84 Isoberlinia angolensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14575 Periploca forrestii Species Cosmopterigidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11408 Podocarpus amarus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16215 Umbilicaria cinereorufescens Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15919 Streptomyces caelestis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17071 Coeloseira pacifica Species Champiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17375 Ceramium botryocarpum Species Ceramiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16455 Xylopia aethiopica Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17218 Helichrysum nudifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16052 Chromodoris obsoleta Species Chromodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16812 Ajuga bracteosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17602 Arbutus menziesii Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4507 Bruguiera gymnorhiza Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16329 Potebniamyces gallicola Species Phacidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2550 Trichoderma citrinum Species Hypocreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9189 Streptomyces atratus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17304 Sipunculus nudus Species Sipunculidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10770 Ptilota pectinata Species Ceramiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16923 Cereus chrysacanthus Species Sagartiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16566 Cinnamosma madagascariensis Species Canellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28319 Ulva prolifera Species Ulvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16456 Mirabilis jalapa Species Nyctaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28868 Pardachirus pavoninus Species Soleidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25550 Buchenavia tetraphylla Species Combretaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15748 Hypoxis nyasica Species Hypoxidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17844 Agaricus integer Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16695 Fumaria kraliki Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8010 Otostegia fruticosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18073 Justicia trinervia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15004 Artemisia taurica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22097 Plakinastrella clathrata Species Plakinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17921 Allium monspessulanum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26788 Sophora viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21437 Rhododendron aureum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17999 Sonneratia alba Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17339 Macaranga sinensis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4336 Echiochilon pauciflorum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15599 Daldinia concentrica Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2155 Tephroseris integrifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9951 Hyella caespitosa Species Hyellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO15545 Veltheimia viridifolia Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13789 Paranephelius uniflorus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14002 Petalostemon purpureum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27058 Aspergillus ustus Species Aspergillaceae 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
NPT1864 Cell line L5178Y Mus musculus EC50 = 1.9 ug.mL-1 PMID[19778087]
NPT681 Cell line PC-12 Rattus norvegicus EC50 > 10.0 ug.mL-1 PMID[19778087]
NPT165 Cell line HeLa Homo sapiens EC50 = 7.5 ug.mL-1 PMID[19778087]

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 NPC179798 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
0.8596 High Similarity NPC56448
0.8475 Intermediate Similarity NPC469496
0.8305 Intermediate Similarity NPC469454
0.8305 Intermediate Similarity NPC469463
0.8167 Intermediate Similarity NPC23046
0.807 Intermediate Similarity NPC5103
0.7742 Intermediate Similarity NPC304180
0.7119 Intermediate Similarity NPC607795
0.5806 Remote Similarity NPC469491
0.55 Remote Similarity NPC258532
0.5072 Remote Similarity NPC603725
0.5072 Remote Similarity NPC610576

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC179798 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
NPD

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