Natural Product: NPC239931

Natural Product IDNPC239931
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Cinnamic Alcohol
IUPAC Name (E)-3-phenylprop-2-en-1-ol
Synonyms (E)-Cinnam Alcohol; Cinnamic Alcohol; Cinnamyl Alcohol
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL324794
PubChem CID 5315892
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002754] Cinnamyl alcohols

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 OOCCDEMITAIZTP-QPJJXVBHSA-N
Standard InCHI InChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+
SMILES OC/C=C/c1ccccc1

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   134.07 Volume:   153.908
?
Van der Waals volume.
Dense:   0.871 LogP:   2.061
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.963
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -1.539
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   2.0 Rigid Bonds:   7.0
TPSA:   20.23
?
Topological Polar Surface Area.
 H-Bond Acceptor:   1.0
H-Bond Donor:   1.0 Rings:   1.0
Heavy Atoms:   1.0

MedChem Properties

QED Drug-Likeness Score:   0.652 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   1.803 Fsp3:   0.111
MCE-18:   4.0
?
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:   Accepted BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.013 Fluc inhibitor:   0.202
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.02
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.083
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   1.0 Promiscuous compounds:   0.116

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.362 MDCK Permeability:   -4.625
Pgp-inhibitor:   0.585 Pgp-substrate:   0.032
PAMPA:   0.254
?
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):   0.061
20% Bioavailability (F20%):   0.58 30% Bioavailability (F30%):   0.932
50% Bioavailability (F50%):   0.76

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.312 MRP1:   0.082
Plasma Protein Binding (PPB):   80.499% Volume Distribution (VD):   0.062
Fu: 17.819%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.825
OATP1B3 inhibitor:   0.938 BCRP inhibitor:   0.155
BSEP inhibitor:   0.88

ADMET: Metabolism

CYP1A2-inhibitor:   0.001 CYP1A2-substrate:   0.003
CYP2C19-inhibitor:   0.002 CYP2C19-substrate:   0.011
CYP2C9-inhibitor:   0.851 CYP2C9-substrate:   0.053
CYP2D6-inhibitor:   0.999 CYP2D6-substrate:   0.001
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.251
CYP2B6-substrate:   0.003 CYP2C8-inhibitor:   0.998
HLM stability:   0.337
?
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):  11.395 Half-life (T1/2):  1.484

ADMET: Toxicity

hERG Blockers:  0.201 hERG Blockers (10um):  0.358
Human Hepatotoxicity (H-HT):  0.811 Drug-induced Liver Injury (DILI):  0.189
AMES Toxicity:  0.511 Rat Oral Acute Toxicity:  0.039
Maximum Recommended Daily Dose:  0.288 Skin Sensitization:  0.973
Carcinogencity:  0.192 Eye Corrosion:  0.744
Eye Irritation:  0.998 Respiratory Toxicity:  0.529
Drug-induced Neurotoxicity:  0.703 Ototoxicity:  0.169
Hematotoxicity:  0.067 Drug-induced Nephrotoxicity:  0.176
Genotoxicity:  0.121 RPMI-8226 Immunitoxicity:  0.041
A549 Cytotoxicity:  0.103 Hek293 Cytotoxicity:  0.123
BCF:   0.423
?
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:   2.944
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.156
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.418
?
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
NPO3347 Vaccinium corymbosum Species Ericaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.ecoenv.2016.07.029]
NPO1524 Rosa rugosa Species Rosaceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodcont.2014.02.001]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jep.2005.01.054]
NPO3347 Vaccinium corymbosum Species Ericaceae Eukaryota Fruit n.a. n.a. DOI[10.1016/S0963-9969(99)00095-2]
NPO9348 Cananga odorata Species Annonaceae Eukaryota fruits n.a. n.a. PMID[11374955]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. root n.a. PMID[15997133]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. root n.a. PMID[16141313]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. fruit n.a. PMID[16378372]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. flower n.a. PMID[16378372]
NPO12830 Styrax tonkinensis Species Styracaceae Eukaryota resin n.a. n.a. PMID[16724846]
NPO9130 Phyllospongia papyracea Species Thorectidae Eukaryota n.a. Papua New Guinea, at depths of 60 ft (914948? S, 15046808? E) n.a. PMID[17455979]
NPO9130 Phyllospongia papyracea Species Thorectidae Eukaryota n.a. n.a. n.a. PMID[17455979]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[17996677]
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota twigs n.a. n.a. PMID[19555125]
NPO1524 Rosa rugosa Species Rosaceae Eukaryota Flowers n.a. n.a. PMID[20467822]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[21504145]
NPO3347 Vaccinium corymbosum Species Ericaceae Eukaryota n.a. fruit n.a. PMID[21648406]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. bark n.a. PMID[21875098]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. callus n.a. PMID[22368856]
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota twigs n.a. n.a. PMID[22677314]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[23611151]
NPO1524 Rosa rugosa Species Rosaceae Eukaryota flower buds n.a. n.a. PMID[24063567]
NPO1524 Rosa rugosa Species Rosaceae Eukaryota Roots n.a. n.a. PMID[24461297]
NPO9348 Cananga odorata Species Annonaceae Eukaryota flower buds Thailand n.a. PMID[24601675]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[24868863]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota roots n.a. n.a. PMID[24931277]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[25089845]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[26562066]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota Twigs n.a. n.a. PMID[28682072]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota Twigs n.a. n.a. PMID[29883114]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[31181920]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[31418264]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota Bark n.a. n.a. PMID[33151073]
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[34332066]
NPO1524 Rosa rugosa Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[34332066]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[34684884]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[34770847]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[36364159]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[36401242]
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[37446712]
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[38688144]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[38754641]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[39459015]
NPO18491 Hyacinthus orientalis Species Hyacinthaceae Eukaryota n.a. n.a. n.a. PMID[9599261]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. root n.a. Database[Article]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27293 Sus scrofa Species Suidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3347 Vaccinium corymbosum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1524 Rosa rugosa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10492 Artemisia montana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10597 Fructus syzygii n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9546 Cinamomum cassia n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO11291 Styrax benzoin Species Styracaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12830 Styrax tonkinensis Species Styracaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10256 Liquidambar orientalis Species Altingiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO30815 Camphora n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO18491 Hyacinthus orientalis Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13822 Aconitum fischeri Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18743 Lagascea mollis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9130 Phyllospongia papyracea Species Thorectidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6288 Talaromyces islandicus Species Trichocomaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19066 Pisolithus arhizus Species Pisolithaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27293 Sus scrofa Species Suidae Eukaryota n.a. n.a. Database[FooDB]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO3347 Vaccinium corymbosum Species Ericaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO3347 Vaccinium corymbosum Species Ericaceae Eukaryota Fruit Juice n.a. n.a. Database[FooDB]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota n.a. n.a. Database[FooDB]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. Database[FooDB]
NPO3347 Vaccinium corymbosum Species Ericaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. Database[FooDB]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30815 Camphora n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO1524 Rosa rugosa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10256 Liquidambar orientalis Species Altingiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13822 Aconitum fischeri Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11291 Styrax benzoin Species Styracaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18491 Hyacinthus orientalis Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10597 Fructus syzygii n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO4156 Apocynum androsaemifolium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3347 Vaccinium corymbosum Species Ericaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10597 Fructus syzygii n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11291 Styrax benzoin Species Styracaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10256 Liquidambar orientalis Species Altingiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1524 Rosa rugosa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14736 Camphora n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO12830 Styrax tonkinensis Species Styracaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18491 Hyacinthus orientalis Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13822 Aconitum fischeri Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4156 Apocynum androsaemifolium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27293 Sus scrofa Species Suidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1524 Rosa rugosa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17954.1 Narcissus tazetta l var. chinensis roem. Varieties Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11291 Styrax benzoin Species Styracaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12830 Styrax tonkinensis Species Styracaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13822 Aconitum fischeri Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10256 Liquidambar orientalis Species Altingiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4156 Apocynum androsaemifolium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9546 Cinamomum cassia n.a. n.a. n.a. n.a. n.a. n.a. Database[TM-MC]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11291 Styrax benzoin Species Styracaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12830 Styrax tonkinensis Species Styracaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10492 Artemisia montana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1524 Rosa rugosa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10256 Liquidambar orientalis Species Altingiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19349 Phlegmariurus yunnanensis Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6288 Talaromyces islandicus Species Trichocomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11751 Tetracera alnifolia Species Dilleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19066 Pisolithus arhizus Species Pisolithaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18491 Hyacinthus orientalis Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1524 Rosa rugosa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17182 Pulmonaria mollis Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4156 Apocynum androsaemifolium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27293 Sus scrofa Species Suidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10492 Artemisia montana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18743 Lagascea mollis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9130 Phyllospongia papyracea Species Thorectidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13822 Aconitum fischeri Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18982 Espeletia grandiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11291 Styrax benzoin Species Styracaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3347 Vaccinium corymbosum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12830 Styrax tonkinensis Species Styracaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10256 Liquidambar orientalis Species Altingiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3689 Cinnamomum verum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7067 Stellera chamaejasme Species Thymelaeaceae 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
NPO31458 Cinnamomum cassia Oil n.a. 0.04 n.a. n.a. % PMID[34332066]
NPO31458 Cinnamomum cassia Oil Bark 0.42 n.a. n.a. % PMID[38688144]
NPO3347 Vaccinium corymbosum Raw Fruit 0.001 0.001 0.001 mg/100g Database [DUKE]
NPO3689 Cinnamomum verum Oil Leaves 0.25 n.a. n.a. % PMID[36364159]
NPO3689 Cinnamomum verum Oil Leaves 1.27 n.a. n.a. % PMID[36364159]
NPO3689 Cinnamomum verum Oil Leaves 0.04 n.a. n.a. % PMID[36364159]
NPO9348 Cananga odorata Oil n.a. 1.96 n.a. n.a. % PMID[39459015]

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
NPT703 Individual protein UDP-glucuronosyltransferase 1-9 Homo sapiens Activity = 90.0 pm/min/mg PMID[10836148]
NPT3936 Individual protein Histamine H4 receptor Rattus norvegicus Inhibition = 33.5 % PMID[12443776]
NPT696 Individual protein UDP-glucuronosyltransferase 2A1 Homo sapiens Activity = 180.0 pm/min/mg PMID[10836148]
NPT967 Individual protein Xanthine dehydrogenase Homo sapiens Inhibition = 47.6 % PMID[22677314]
NPT967 Individual protein Xanthine dehydrogenase Homo sapiens IC50 > 50.0 ug.mL-1 PMID[22677314]
NPT43 Individual protein Tyrosinase Agaricus bisporus IC50 > 10000000.0 nM PMID[19555125]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1033 Organism Enterobacter cloacae Enterobacter cloacae MIC = 7450000.0 nM DOI[10.1007/s00044-013-0484-9]
NPT21 Organism Aspergillus niger Aspergillus niger MIC = 3720000.0 nM DOI[10.1007/s00044-013-0484-9]
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 7450000.0 nM DOI[10.1007/s00044-013-0484-9]
NPT1264 Organism Burkholderia cepacia Burkholderia cepacia MIC = 1860000.0 nM DOI[10.1007/s00044-013-0484-9]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 7450000.0 nM DOI[10.1007/s00044-013-0484-9]
NPT20 Organism Candida albicans Candida albicans MIC = 1860000.0 nM DOI[10.1007/s00044-013-0484-9]
NPT1262 Organism Aspergillus parasiticus Aspergillus parasiticus MIC = 3720000.0 nM DOI[10.1007/s00044-013-0484-9]
NPT329 Organism Trichophyton rubrum Trichophyton rubrum MIC = 1860000.0 nM DOI[10.1007/s00044-013-0484-9]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae MIC = 3720000.0 nM DOI[10.1007/s00044-013-0484-9]
NPT187 Organism Issatchenkia orientalis Pichia kudriavzevii MIC = 3720000.0 nM DOI[10.1007/s00044-013-0484-9]
NPT1263 Organism Aspergillus sydowii Aspergillus sydowii MIC = 3720000.0 nM DOI[10.1007/s00044-013-0484-9]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 3720000.0 nM DOI[10.1007/s00044-013-0484-9]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 14900000.0 nM DOI[10.1007/s00044-013-0484-9]
NPT19 Organism Escherichia coli Escherichia coli MIC = 7450000.0 nM DOI[10.1007/s00044-013-0484-9]
NPT522 Organism Abutilon theophrasti Abutilon theophrasti Activity = 0.0 % DOI[10.1021/np50043a024]
NPT522 Organism Abutilon theophrasti Abutilon theophrasti Activity = 73.0 % DOI[10.1021/np50043a024]
NPT2 Others Unspecified n.a. IC50 = 250000.0 nM PMID[26494261]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT593 Organism Bursaphelenchus xylophilus Bursaphelenchus xylophilus mortality = 11.3 % PMID[18605734]
NPT593 Organism Bursaphelenchus xylophilus Bursaphelenchus xylophilus mortality = 57.6 % PMID[18605734]
NPT593 Organism Bursaphelenchus xylophilus Bursaphelenchus xylophilus mortality = 99.5 % PMID[18605734]
NPT593 Organism Bursaphelenchus xylophilus Bursaphelenchus xylophilus mortality = 100.0 % PMID[18605734]
NPT25256 Organism Attelabidae Attelabidae mortality = 50.0 % PMID[10888580]
NPT29 Organism Rattus norvegicus Rattus norvegicus Inhibition = 13.0 % PMID[26494261]





 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 NPC239931 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
1.0 High Similarity NPC82770
1.0 High Similarity NPC78954
0.6071 Remote Similarity NPC104216
0.5833 Remote Similarity NPC269586
0.5484 Remote Similarity NPC4718
0.5333 Remote Similarity NPC131587
0.5172 Remote Similarity NPC176940

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC239931 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