Natural Product: NPC297517

Natural Product IDNPC297517
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 3,4-Dicaffeoyl Quinic Acid
IUPAC Name (1S,3S,4R,5S)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid
Synonyms 3,4-Dicaffeoyl Quinic Acid
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL453537
PubChem CID 10324242
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000129] Alcohols and polyols
          • [CHEMONTID:0001292] Cyclic alcohols and derivatives
            • [CHEMONTID:0002509] Cyclitols and derivatives
              • [CHEMONTID:0002512] Quinic acids and derivatives

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 UFCLZKMFXSILNL-KDBOUVDRSA-N
Standard InCHI InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/p-1/b7-3+,8-4+/t19-,20-,23+,25-/m0/s1
SMILES c1cc(c(cc1/C=C/C(=O)O[C@H]1C[C@@](C[C@@H]([C@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)O)(C(=O)O)O)O)[O-]

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   516.13 Volume:   491.768
?
Van der Waals volume.
Dense:   1.05 LogP:   1.285
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.349
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.845
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   9.0 Rigid Bonds:   23.0
TPSA:   211.28
?
Topological Polar Surface Area.
 H-Bond Acceptor:   12.0
H-Bond Donor:   7.0 Rings:   3.0
Heavy Atoms:   12.0

MedChem Properties

QED Drug-Likeness Score:   0.156 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   4.141 Fsp3:   0.24
MCE-18:   81.29
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Accepted
Pfizer Rule:   Rejected GSK Rule:   Accepted
Golden Triangle Rule:   Accepted BMS Rule:   0
Chelating Alert:   1 PAINS Alert:   1
Colloidal aggregators:   0.767 Fluc inhibitor:   1.0
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.179
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.628
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.553 Promiscuous compounds:   0.398

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -6.659 MDCK Permeability:   -5.025
Pgp-inhibitor:   0.0 Pgp-substrate:   0.002
PAMPA:   0.999
?
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):   0.044
20% Bioavailability (F20%):   1.0 30% Bioavailability (F30%):   1.0
50% Bioavailability (F50%):   1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.0 MRP1:   0.096
Plasma Protein Binding (PPB):   66.215% Volume Distribution (VD):   -0.049
Fu: 25.939%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   1.0
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.002
BSEP inhibitor:   0.006

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.0 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.001
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   1.0
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.0
?
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):  5.689 Half-life (T1/2):  2.393

ADMET: Toxicity

hERG Blockers:  0.037 hERG Blockers (10um):  0.198
Human Hepatotoxicity (H-HT):  0.657 Drug-induced Liver Injury (DILI):  0.56
AMES Toxicity:  0.525 Rat Oral Acute Toxicity:  0.152
Maximum Recommended Daily Dose:  0.818 Skin Sensitization:  1.0
Carcinogencity:  0.159 Eye Corrosion:  0.005
Eye Irritation:  0.803 Respiratory Toxicity:  0.301
Drug-induced Neurotoxicity:  0.007 Ototoxicity:  0.93
Hematotoxicity:  0.015 Drug-induced Nephrotoxicity:  0.247
Genotoxicity:  0.923 RPMI-8226 Immunitoxicity:  0.009
A549 Cytotoxicity:  0.977 Hek293 Cytotoxicity:  0.273
BCF:   0.562
?
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:   3.398
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.797
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.522
?
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
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. PMID[ 21030913]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1002/elan.200403102]
NPO24105 Artemisia iwayomogi Species Asteraceae Eukaryota n.a. aerial part n.a. DOI[10.1002/hlca.201300170.]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. leaf n.a. DOI[10.1007/s11418-006-0112-9]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. stem n.a. DOI[10.1007/s11418-006-0112-9]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. flower n.a. DOI[10.1007/s11418-006-0112-9]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11627-001-0052-8]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2009.03.042]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2012.02.124]
NPO10374 Dichrocephala bicolor Species Asteraceae Eukaryota n.a. whole plant n.a. DOI[10.1021/np980153o]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.3136/fstr.15.499]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB10.140]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB2010.000-3252]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/JMPR.9000078]
NPO10374 Dichrocephala bicolor Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[10096846]
NPO523 Tussilago farfara Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[10543912]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[11077184]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. flower n.a. PMID[12130858]
NPO24105 Artemisia iwayomogi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[12735688]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[17328234]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[18321056]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[18341288]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. whole plant n.a. PMID[21428416]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower n.a. PMID[21804227]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower bud n.a. PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota flower buds Henan province, China 2005-MAY PMID[21942812]
NPO17072 Lonicera macranthoides Species Caprifoliaceae Eukaryota n.a. flower bud n.a. PMID[22822669]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[22870812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. leaf n.a. PMID[23265495]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23435948]
NPO24105 Artemisia iwayomogi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23510022]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[24279769]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers Tongxiang, China n.a. PMID[24621197]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[25737008]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[26099993]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28156114]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28248102]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[29400471]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Aerial Parts n.a. n.a. PMID[30726671]
NPO28688 Aster tataricus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[30931559]
NPO523 Tussilago farfara Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[32881525]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. PMID[6387056]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4596 Lonicera confusa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21345 Lonicera hypoglauca Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17072 Lonicera macranthoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10861 Dipsacus asper Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO523 Tussilago farfara Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16931 Cichorium glandulosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24105 Artemisia iwayomogi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28688 Aster tataricus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10374 Dichrocephala bicolor Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota Roots n.a. Database[FooDB]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29271 Erycibe obtusifolia Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO523 Tussilago farfara Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28688 Aster tataricus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12329 Erycibe schmidtii Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4014 Erigeron breviscapus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12329 Erycibe schmidtii Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28688 Aster tataricus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO523 Tussilago farfara Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17072 Lonicera macranthoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4014 Erigeron breviscapus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4596 Lonicera confusa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29271 Erycibe obtusifolia Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21345 Lonicera hypoglauca Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21345 Lonicera hypoglauca Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28688 Aster tataricus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO523 Tussilago farfara Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12329 Erycibe schmidtii Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29271 Erycibe obtusifolia Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO523 Tussilago farfara Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21345 Lonicera hypoglauca Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24105 Artemisia iwayomogi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4014 Erigeron breviscapus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17072 Lonicera macranthoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28688 Aster tataricus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16931 Cichorium glandulosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4596 Lonicera confusa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12329 Erycibe schmidtii Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10861 Dipsacus asper Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29271 Erycibe obtusifolia Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10861 Dipsacus asper Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21345 Lonicera hypoglauca Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28688 Aster tataricus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24105 Artemisia iwayomogi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16931 Cichorium glandulosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4014 Erigeron breviscapus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17072 Lonicera macranthoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10374 Dichrocephala bicolor Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO523 Tussilago farfara Species Asteraceae 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
NPT2 Others Unspecified n.a. Activity = 78.4 % PMID[10096846]
NPT2 Others Unspecified n.a. Activity = 725.5 cpm PMID[10096846]
NPT2 Others Unspecified n.a. Activity = 30.5 pg/ml PMID[10096846]
NPT2 Others Unspecified n.a. EC50 = 8.1 ug.mL-1 PMID[10096846]
NPT2 Others Unspecified n.a. EC50 = 4.4 ug.mL-1 PMID[10096846]
NPT2 Others Unspecified n.a. EC50 = 5.0 ug.mL-1 PMID[10096846]
NPT2 Others Unspecified n.a. EC50 = 1.25 ug.mL-1 PMID[10096846]

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 NPC297517 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
0.8852 High Similarity NPC206095
0.8852 High Similarity NPC35702
0.8852 High Similarity NPC224389
0.8308 Intermediate Similarity NPC477335
0.7324 Intermediate Similarity NPC42464
0.7105 Intermediate Similarity NPC145425
0.6667 Remote Similarity NPC219428
0.6571 Remote Similarity NPC278068
0.6286 Remote Similarity NPC37250
0.6286 Remote Similarity NPC142703
0.6286 Remote Similarity NPC152942
0.6286 Remote Similarity NPC9991
0.6286 Remote Similarity NPC302857
0.6286 Remote Similarity NPC477333
0.6286 Remote Similarity NPC600892
0.6207 Remote Similarity NPC488321
0.6207 Remote Similarity NPC488319
0.6207 Remote Similarity NPC488320
0.6176 Remote Similarity NPC13818
0.5833 Remote Similarity NPC471027
0.5479 Remote Similarity NPC319628
0.527 Remote Similarity NPC277315
0.527 Remote Similarity NPC472016
0.527 Remote Similarity NPC192831
0.5263 Remote Similarity NPC477334
0.5217 Remote Similarity NPC488563
0.5205 Remote Similarity NPC68517
0.5075 Remote Similarity NPC474275
0.5075 Remote Similarity NPC147192
0.5075 Remote Similarity NPC224208
0.5075 Remote Similarity NPC41661

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC297517 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