Natural Product: NPC84786

Natural Product IDNPC84786
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Carnosol
IUPAC Name n.a.
Synonyms Carnosol
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL218693
PubChem CID 442009
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

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 XUSYGBPHQBWGAD-PJSUUKDQSA-N
Standard InCHI InChI=1S/C20H26O4/c1-10(2)11-8-12-13-9-14-19(3,4)6-5-7-20(14,18(23)24-13)15(12)17(22)16(11)21/h8,10,13-14,21-22H,5-7,9H2,1-4H3/t13-,14-,20+/m0/s1
SMILES O=C1O[C@H]2C[C@@H]3[C@]1(CCCC3(C)C)c1c2cc(c(c1O)O)C(C)C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   330.18 Volume:   344.865
?
Van der Waals volume.
Dense:   0.957 LogP:   3.11
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.9
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.077
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   1.0 Rigid Bonds:   20.0
TPSA:   66.76
?
Topological Polar Surface Area.
 H-Bond Acceptor:   4.0
H-Bond Donor:   2.0 Rings:   5.0
Heavy Atoms:   4.0

MedChem Properties

QED Drug-Likeness Score:   0.595 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   5.256 Fsp3:   0.65
MCE-18:   121.091
?
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:   0
Chelating Alert:   1 PAINS Alert:   1
Colloidal aggregators:   0.525 Fluc inhibitor:   0.01
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.228
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.025
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.255 Promiscuous compounds:   0.016

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.767 MDCK Permeability:   -4.717
Pgp-inhibitor:   0.254 Pgp-substrate:   0.017
PAMPA:   0.072
?
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):   0.0
20% Bioavailability (F20%):   0.105 30% Bioavailability (F30%):   0.074
50% Bioavailability (F50%):   0.785

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.179 MRP1:   0.998
Plasma Protein Binding (PPB):   95.06% Volume Distribution (VD):   0.381
Fu: 6.217%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.959
OATP1B3 inhibitor:   0.522 BCRP inhibitor:   0.013
BSEP inhibitor:   0.974

ADMET: Metabolism

CYP1A2-inhibitor:   0.009 CYP1A2-substrate:   0.006
CYP2C19-inhibitor:   0.061 CYP2C19-substrate:   0.174
CYP2C9-inhibitor:   0.0 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.121
CYP3A4-inhibitor:   0.926 CYP3A4-substrate:   0.034
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.13
HLM stability:   0.127
?
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):  12.709 Half-life (T1/2):  1.625

ADMET: Toxicity

hERG Blockers:  0.057 hERG Blockers (10um):  0.496
Human Hepatotoxicity (H-HT):  0.694 Drug-induced Liver Injury (DILI):  0.763
AMES Toxicity:  0.81 Rat Oral Acute Toxicity:  0.836
Maximum Recommended Daily Dose:  0.98 Skin Sensitization:  0.988
Carcinogencity:  0.934 Eye Corrosion:  0.004
Eye Irritation:  0.366 Respiratory Toxicity:  0.912
Drug-induced Neurotoxicity:  0.525 Ototoxicity:  0.568
Hematotoxicity:  0.693 Drug-induced Nephrotoxicity:  0.993
Genotoxicity:  0.956 RPMI-8226 Immunitoxicity:  0.178
A549 Cytotoxicity:  0.715 Hek293 Cytotoxicity:  0.476
BCF:   2.007
?
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:   4.606
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   6.05
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   5.642
?
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
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[10096857]
NPO40965 Nocardia sp. NRRL 5646 Strain Nocardiaceae Bacteria n.a. n.a. n.a. PMID[12350144]
NPO25701 Amentotaxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[12880325]
NPO17119 Dalea versicolor Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[15043439]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[1567426]
NPO18606 Achyrocline bogotensis Species Asteraceae Eukaryota n.a. Colombian n.a. PMID[15844937]
NPO20067 Salvia pachyphylla Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17190465]
NPO2794 Salvia clevelandii Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17190465]
NPO25813 Salvia przewalskii Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[17217287]
NPO23470 Orthosiphon labiatus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17256988]
NPO32827 salvia africana-lutea Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17256988]
NPO3291 Cynanchum auriculatum Species Apocynaceae Eukaryota n.a. root n.a. PMID[18401845]
NPO19020 Salvia canariensis Species Lamiaceae Eukaryota stems and leaves n.a. n.a. PMID[19711987]
NPO17362 Alstonia yunnanensis Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[19775092]
NPO18055 Isodon adenolomus Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[21534539]
NPO18055 Isodon adenolomus Species Lamiaceae Eukaryota aerial parts Shangrila, Yunnan Province, China 2008-AUG PMID[21534539]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23507152]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[33321838]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[35889256]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[36432812]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[36677644]
NPO21031 Dracocephalum moldavica Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[36838592]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[36840093]
NPO24456 Salvia lavandulifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[36986494]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[36987013]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[37176852]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[37570961]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[37751472]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[37836118]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[37836125]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[38474654]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[38617605]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[38695450]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[39063231]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[39135848]
NPO18048 Phlomis crinita Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[39419301]
NPO19020 Salvia canariensis Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[8759159]
NPO12148.2 Acer pictum subsp. okamotoanum Subspecies Sapindaceae Eukaryota n.a. n.a. n.a. PMID[9461665]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18048 Phlomis crinita Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28257 Dioscorea communis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO415 Deguelia hatschbachii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25212 Ritterella rubra n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO25813 Salvia przewalskii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22016 Notholaena dealbata Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17119 Dalea versicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25701 Amentotaxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18055 Isodon adenolomus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24456 Salvia lavandulifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4009 Allochromatium minutissimum Species Chromatiaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO23960 Artemisia siversiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27437 Camptothecium lutescens Species Brachytheciaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26223 Cladonia bellidiflora Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25868 Decachaeta ovatifolia n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO12476 Delphinium cyphoplectrum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26087 Euphorbia retusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10497 Hydrolithon reinboldii Species Corallinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26054 Palmaria palmata Species Palmariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6346 Phallusia fumigata Species Ascidiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26316 Pleurophycus gardneri Species Alariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23417 Rhabdia lycioides n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO10155 Stauntonia obovatifoliola Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25974 Streptomyces lateritius Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO24740 Uvaria klaineana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24988 Viburnum sieboldi Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12148.2 Acer pictum subsp. okamotoanum Subspecies Sapindaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18606 Achyrocline bogotensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17362 Alstonia yunnanensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19522 Arthropsis truncata Species n.a. Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13832 Aspilia hispida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17911 Blepharisma japonicum Species Blepharismidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15497 Caria ino Species Riodinidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2377 Cetraria ciliaris Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19580 Chamaemelum fuscatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3291 Cynanchum auriculatum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19311 Dasymaschalon blumei Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16567 Doriopsilla areolata Species Dendrodorididae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10852 Felimare midatlantica Species Chromodorididae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17643 Penicillium pedemontanum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19777 Pholiota adiposa Species Strophariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4230 Protoparmeliopsis peltata Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4984 Salvia cana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19638 Scutellaria albida Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13414 Senecio fuertesii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17783 Sideritis cystosiphon Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18356 Stachys tuberifera Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16997 Talaromyces aculeatus Species Trichocomaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18435 Tylophora atrofolliculata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16990 Verbesina virgata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23470 Orthosiphon labiatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20067 Salvia pachyphylla Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota Tissue Culture n.a. n.a. Database[FooDB]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25701 Amentotaxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18435 Tylophora atrofolliculata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17362 Alstonia yunnanensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25813 Salvia przewalskii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3291 Cynanchum auriculatum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18356 Stachys tuberifera Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO25813 Salvia przewalskii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28257 Dioscorea communis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18356 Stachys tuberifera Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3291 Cynanchum auriculatum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17362 Alstonia yunnanensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25701 Amentotaxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18435 Tylophora atrofolliculata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19020 Salvia canariensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24740 Uvaria klaineana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3291 Cynanchum auriculatum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17362 Alstonia yunnanensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26223 Cladonia bellidiflora Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23417 Rhabdia lycioides n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO6346 Phallusia fumigata Species Ascidiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25974 Streptomyces lateritius Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO415 Deguelia hatschbachii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24988 Viburnum sieboldi Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10852 Felimare midatlantica Species Chromodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18055 Isodon adenolomus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4009 Allochromatium minutissimum Species Chromatiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO22016 Notholaena dealbata Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3291 Cynanchum auriculatum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26054 Palmaria palmata Species Palmariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18048 Phlomis crinita Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24740 Uvaria klaineana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17911 Blepharisma japonicum Species Blepharismidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15497 Caria ino Species Riodinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2377 Cetraria ciliaris Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25868 Decachaeta ovatifolia n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26087 Euphorbia retusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21031 Dracocephalum moldavica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13414 Senecio fuertesii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19580 Chamaemelum fuscatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28257 Dioscorea communis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25701 Amentotaxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12476 Delphinium cyphoplectrum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4984 Salvia cana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25813 Salvia przewalskii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19638 Scutellaria albida Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4230 Protoparmeliopsis peltata Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10497 Hydrolithon reinboldii Species Corallinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19522 Arthropsis truncata Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19311 Dasymaschalon blumei Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17783 Sideritis cystosiphon Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2794 Salvia clevelandii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17362 Alstonia yunnanensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23960 Artemisia siversiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16997 Talaromyces aculeatus Species Trichocomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17643 Penicillium pedemontanum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16990 Verbesina virgata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27437 Camptothecium lutescens Species Brachytheciaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18356 Stachys tuberifera Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25212 Ritterella rubra n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16567 Doriopsilla areolata Species Dendrodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10155 Stauntonia obovatifoliola Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18435 Tylophora atrofolliculata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26316 Pleurophycus gardneri Species Alariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18606 Achyrocline bogotensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19777 Pholiota adiposa Species Strophariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19020 Salvia canariensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24456 Salvia lavandulifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12148.2 Acer pictum subsp. okamotoanum Subspecies Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17119 Dalea versicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13832 Aspilia hispida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23470 Orthosiphon labiatus Species Lamiaceae 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
NPO18048 Phlomis crinita Methanolic extract Flowers 0.07 ± 0.00 n.a. n.a. % PMID[39419301]
NPO21031 Dracocephalum moldavica n.a. n.a. 0.003 ± 0.0005 n.a. n.a. mg/mL PMID[36838592]
NPO24456 Salvia lavandulifolia n.a. n.a. 3.97 n.a. n.a. % PMID[36986494]
NPO42012 Rosmarinus officinalis Other Leaf 516.65 53 980.3 mg/100g Database [DUKE]
NPO42012 Rosmarinus officinalis Raw n.a. 52.99999619 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO42012 Rosmarinus officinalis n.a. n.a. 53 n.a. n.a. mg/100g of FW Database [Phenol-Explorer]

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
NPT2797 Individual protein Pancreatic lipase Homo sapiens IC50 = 13000.0 nM PMID[17521912]
NPT202 Individual protein Protease Human immunodeficiency virus 1 IC90 > 10.0 ug.mL-1 PMID[8229021]
NPT1651 Individual protein Nuclear factor erythroid 2-related factor 2 Mus musculus FC = 50.0 n.a. PMID[23507152]
NPT1384 Individual protein Farnesyl diphosphate synthase Homo sapiens IC50 = 13300.0 nM PMID[31725297]
NPT956 Individual protein Prostaglandin E synthase Homo sapiens IC50 = 5000.0 nM DOI[10.1039/C5MD00278H]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT179 Cell line A2780 Homo sapiens GI50 = 3600.0 nM PMID[17190465]
NPT1577 Cell line SW1573 Homo sapiens GI50 = 10000.0 nM PMID[17190465]
NPT1183 Cell line WiDr Homo sapiens GI50 = 26000.0 nM PMID[17190465]
NPT396 Cell line T47D Homo sapiens GI50 = 24000.0 nM PMID[17190465]
NPT1723 Cell line HBL-100 Homo sapiens GI50 = 3900.0 nM PMID[17190465]
NPT189 Cell line Vero Chlorocebus aethiops IC50 > 60000.0 nM PMID[19711987]
NPT165 Cell line HeLa Homo sapiens IC50 > 60000.0 nM PMID[19711987]
NPT81 Cell line A549 Homo sapiens IC50 > 60000.0 nM PMID[19711987]
NPT189 Cell line Vero Chlorocebus aethiops IC50 = 51500.0 nM PMID[19711987]
NPT81 Cell line A549 Homo sapiens IC50 = 47000.0 nM PMID[19711987]
NPT83 Cell line MCF7 Homo sapiens IC50 = 44500.0 nM PMID[19711987]
NPT165 Cell line HeLa Homo sapiens IC50 = 43900.0 nM PMID[19711987]
NPT83 Cell line MCF7 Homo sapiens IC50 = 40900.0 nM PMID[19711987]
NPT172 Organism Proteus mirabilis Proteus mirabilis MIC > 40.0 ug.mL-1 PMID[19711987]
NPT1246 Organism Salmonella Salmonella MIC > 40.0 ug.mL-1 PMID[19711987]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC > 40.0 ug.mL-1 PMID[19711987]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 4.0 ug.mL-1 PMID[19711987]
NPT20 Organism Candida albicans Candida albicans MIC = 20.0 ug.mL-1 PMID[19711987]
NPT564 Organism Listeria monocytogenes Listeria monocytogenes Inhibition = 27.6 % PMID[33378620]
NPT564 Organism Listeria monocytogenes Listeria monocytogenes Inhibition = 40.4 % PMID[33378620]
NPT564 Organism Listeria monocytogenes Listeria monocytogenes Inhibition = 46.7 % PMID[33378620]
NPT564 Organism Listeria monocytogenes Listeria monocytogenes Inhibition = 17.2 % PMID[33378620]
NPT1 Others Radical scavenging activity n.a. IC50 = 114000.0 nM PMID[12350144]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 40.0 ug.mL-1 PMID[19711987]
NPT19 Organism Escherichia coli Escherichia coli MIC > 40.0 ug.mL-1 PMID[19711987]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MIC > 40.0 ug.mL-1 PMID[19711987]
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MIC = 5.0 ug.mL-1 PMID[19711987]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 25.0 ug.mL-1 PMID[19711987]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 0.0 % PMID[33378620]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 5.4 % PMID[33378620]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Inhibition = 84.8 % PMID[33378620]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 39.0 % PMID[33378620]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Inhibition = 95.9 % PMID[33378620]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 88.5 % PMID[33378620]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 0.0 % PMID[33378620]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Inhibition = 68.2 % PMID[33378620]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Inhibition = 100.0 % PMID[33378620]
NPT314 Organism Bacillus cereus Bacillus cereus MIC = 5.0 ug.mL-1 PMID[19711987]
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii Inhibition = 47.2 % PMID[33378620]
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii Inhibition = 43.2 % PMID[33378620]
NPT1286 Organism Pectobacterium carotovorum Pectobacterium carotovorum Inhibition = 69.1 % PMID[33378620]
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii Inhibition = 49.0 % PMID[33378620]
NPT1286 Organism Pectobacterium carotovorum Pectobacterium carotovorum Inhibition = 49.1 % PMID[33378620]
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii Inhibition = 7.1 % PMID[33378620]
NPT1286 Organism Pectobacterium carotovorum Pectobacterium carotovorum Inhibition = 100.0 % PMID[33378620]
NPT1286 Organism Pectobacterium carotovorum Pectobacterium carotovorum Inhibition = 35.8 % PMID[33378620]

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 NPC84786 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
0.8727 High Similarity NPC487093
0.8571 High Similarity NPC474991
0.6667 Remote Similarity NPC127046
0.6333 Remote Similarity NPC99795
0.5909 Remote Similarity NPC191899
0.5846 Remote Similarity NPC246229
0.5846 Remote Similarity NPC605250
0.5075 Remote Similarity NPC223573

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC84786 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