Natural Product: NPC80186

Natural Product IDNPC80186
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 GKENRJIRKFSNED-UKILVPOCSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID 21721878
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0000337] Flavans
          • [CHEMONTID:0003642] 8-prenylated flavans
            • [CHEMONTID:0003508] 8-prenylated flavanones

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 GKENRJIRKFSNED-UKILVPOCSA-N
Standard InCHI InChI=1S/C25H28O7/c1-12(2)5-8-16-20(28)17(9-6-13(3)4)24-19(21(16)29)22(30)23(31)25(32-24)15-10-7-14(26)11-18(15)27/h5-7,10-11,23,25-29,31H,8-9H2,1-4H3/t23-,25+/m0/s1
SMILES CC(=CCc1c(c(CC=C(C)C)c2c(c1O)C(=O)[C@@H]([C@@H](c1ccc(cc1O)O)O2)O)O)C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   440.18 Volume:   453.09
?
Van der Waals volume.
Dense:   0.972 LogP:   3.494
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.11
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.583
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   5.0 Rigid Bonds:   20.0
TPSA:   127.45
?
Topological Polar Surface Area.
 H-Bond Acceptor:   7.0
H-Bond Donor:   5.0 Rings:   3.0
Heavy Atoms:   7.0

MedChem Properties

QED Drug-Likeness Score:   0.441 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.973 Fsp3:   0.32
MCE-18:   71.788
?
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:   Accepted
Golden Triangle Rule:   Rejected BMS Rule:   1
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.779 Fluc inhibitor:   0.329
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.682
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.597
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.41 Promiscuous compounds:   0.127

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.619 MDCK Permeability:   -4.846
Pgp-inhibitor:   0.957 Pgp-substrate:   0.027
PAMPA:   0.638
?
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):   0.342
20% Bioavailability (F20%):   0.967 30% Bioavailability (F30%):   1.0
50% Bioavailability (F50%):   1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.0 MRP1:   0.9
Plasma Protein Binding (PPB):   94.077% Volume Distribution (VD):   0.375
Fu: 6.596%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   1.0
OATP1B3 inhibitor:   0.999 BCRP inhibitor:   0.962
BSEP inhibitor:   0.374

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   1.0
CYP2C19-inhibitor:   0.336 CYP2C19-substrate:   1.0
CYP2C9-inhibitor:   0.015 CYP2C9-substrate:   0.014
CYP2D6-inhibitor:   0.16 CYP2D6-substrate:   0.146
CYP3A4-inhibitor:   0.243 CYP3A4-substrate:   1.0
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   1.0
?
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):  3.949 Half-life (T1/2):  2.518

ADMET: Toxicity

hERG Blockers:  0.03 hERG Blockers (10um):  0.423
Human Hepatotoxicity (H-HT):  0.93 Drug-induced Liver Injury (DILI):  0.428
AMES Toxicity:  0.695 Rat Oral Acute Toxicity:  0.935
Maximum Recommended Daily Dose:  0.609 Skin Sensitization:  0.999
Carcinogencity:  0.21 Eye Corrosion:  0.0
Eye Irritation:  0.753 Respiratory Toxicity:  0.768
Drug-induced Neurotoxicity:  0.612 Ototoxicity:  0.609
Hematotoxicity:  0.223 Drug-induced Nephrotoxicity:  0.977
Genotoxicity:  0.998 RPMI-8226 Immunitoxicity:  0.201
A549 Cytotoxicity:  0.927 Hek293 Cytotoxicity:  0.874
BCF:   1.888
?
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:   5.007
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   6.718
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   6.092
?
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
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10654410]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[10843587]
NPO20142 Embelia schimperi Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[11054840]
NPO18668 Asimina parviflora Species Annonaceae Eukaryota twigs n.a. n.a. PMID[1453182]
NPO19667 Hypericum styphelioides Species Hypericaceae Eukaryota n.a. leaf n.a. PMID[15165152]
NPO19667 Hypericum styphelioides Species Hypericaceae Eukaryota leaves n.a. n.a. PMID[15165152]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[15568770]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. PMID[15911254]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16392664]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota roots Hualien Hsien, Taiwan 2003-JUL PMID[16933887]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16933887]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[17951038]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[18175961]
NPO20879 Clerodendrum bungei Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[18348535]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. root n.a. PMID[18975262]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. n.a. n.a. PMID[19407970]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. bark n.a. PMID[21553897]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24295087]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. PMID[24333010]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[24459770]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[27575476]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[30298740]
NPO20879 Clerodendrum bungei Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[34142352]
NPO20489 Epilobium hirsutum Species Onagraceae Eukaryota n.a. n.a. n.a. PMID[36670952]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[9868163]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. Database[Article]
NPO21495 Abelia chinensis Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20421 Aplophyllum alberti-regelii n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO18668 Asimina parviflora Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20084 Atraphaxis spinosa Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19995 Baccharis neglecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17849 Centaurea maculosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12056 Chondrodendron tomentosum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20879 Clerodendrum bungei Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5903 Conus mus Species Conidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22961 Cordia leucocephala Species Cordiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18143 Dendronephthya griffini Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21562 Diospyros assimilis Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19511 Dolabella californica Species Aplysiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20142 Embelia schimperi Species Primulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20489 Epilobium hirsutum Species Onagraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21108 Eria anomala Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11523 Erysimum leptophyllum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20680 Erythrina melanacantha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19036 Esenbeckia leiocarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21631 Faramea salicifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16569 Gymnocalycium schickendantzii Species Cactaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12313 Haplophyllum obtusifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28202 Helichrysum tenuifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19667 Hypericum styphelioides Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27367 Latrunculia magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21038 Lemaireocereus longispinus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20843 Monsonia senegalensis Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19810 Myxococcus stipitatus Species Myxococcaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17560 Pancratium sickenbergeri Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16141 Piper regnellii Species Piperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14241 Planchonia grandis Species Asterolecaniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18473 Plathymenia reticulata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18866 Pteridium esculentum Species Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17258 Rhinella marina Species Bufonidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9968 Shigella dysenteriae Species Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO20624 Simarouba glauca Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21243 Siphonaria capensis Species Siphonariidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13449 Syzygium polycephaloides Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28072 Theonella conica Species Theonellidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4051 Tricholoma columbetta Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19912 Vellozia nanuzae Species Velloziaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22937 Vernonia fagifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12056 Chondrodendron tomentosum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18668 Asimina parviflora Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20489 Epilobium hirsutum Species Onagraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20142 Embelia schimperi Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20680 Erythrina melanacantha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20879 Clerodendrum bungei Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12056 Chondrodendron tomentosum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20680 Erythrina melanacantha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[Title]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18473 Plathymenia reticulata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21631 Faramea salicifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20084 Atraphaxis spinosa Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16569 Gymnocalycium schickendantzii Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20489 Epilobium hirsutum Species Onagraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17849 Centaurea maculosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20680 Erythrina melanacantha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4051 Tricholoma columbetta Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12313 Haplophyllum obtusifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21562 Diospyros assimilis Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9968 Shigella dysenteriae Species Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO21495 Abelia chinensis Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19511 Dolabella californica Species Aplysiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5903 Conus mus Species Conidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20879 Clerodendrum bungei Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20142 Embelia schimperi Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20421 Aplophyllum alberti-regelii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21243 Siphonaria capensis Species Siphonariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21108 Eria anomala Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16141 Piper regnellii Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17560 Pancratium sickenbergeri Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19810 Myxococcus stipitatus Species Myxococcaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO20843 Monsonia senegalensis Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19036 Esenbeckia leiocarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21038 Lemaireocereus longispinus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28202 Helichrysum tenuifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19667 Hypericum styphelioides Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18143 Dendronephthya griffini Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19995 Baccharis neglecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11523 Erysimum leptophyllum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28072 Theonella conica Species Theonellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13449 Syzygium polycephaloides Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14241 Planchonia grandis Species Asterolecaniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18866 Pteridium esculentum Species Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18668 Asimina parviflora Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27367 Latrunculia magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22961 Cordia leucocephala Species Cordiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22937 Vernonia fagifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12056 Chondrodendron tomentosum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17258 Rhinella marina Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20624 Simarouba glauca Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19912 Vellozia nanuzae Species Velloziaceae 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

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 NPC80186 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
0.7833 Intermediate Similarity NPC254412
0.7077 Intermediate Similarity NPC138288
0.6875 Remote Similarity NPC285555
0.6308 Remote Similarity NPC262038
0.6308 Remote Similarity NPC319910
0.5972 Remote Similarity NPC216035
0.597 Remote Similarity NPC35567
0.5588 Remote Similarity NPC265040
0.5571 Remote Similarity NPC293286
0.5571 Remote Similarity NPC278476
0.5441 Remote Similarity NPC324436
0.5441 Remote Similarity NPC78
0.5429 Remote Similarity NPC223500
0.5397 Remote Similarity NPC279417
0.5397 Remote Similarity NPC49130
0.5195 Remote Similarity NPC304207
0.5143 Remote Similarity NPC187282
0.5139 Remote Similarity NPC608140
0.5072 Remote Similarity NPC1486
0.507 Remote Similarity NPC243171
0.507 Remote Similarity NPC482705
0.507 Remote Similarity NPC610133
0.5063 Remote Similarity NPC485616
0.5063 Remote Similarity NPC217149

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC80186 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