Natural Product: NPC176869

Natural Product IDNPC176869
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 7-O-Methyl-Aromadendrin
IUPAC Name (2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL491541
PubChem CID 181132
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0002585] O-methylated flavonoids
          • [CHEMONTID:0002592] 7-O-methylated flavonoids

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 LZLGHWHSUZVUFZ-JKSUJKDBSA-N
Standard InCHI InChI=1S/C16H14O6/c1-21-10-6-11(18)13-12(7-10)22-16(15(20)14(13)19)8-2-4-9(17)5-3-8/h2-7,15-18,20H,1H3/t15-,16+/m0/s1
SMILES COc1cc(c2c(c1)O[C@H](c1ccc(cc1)O)[C@H](C2=O)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   302.08 Volume:   293.909
?
Van der Waals volume.
Dense:   1.028 LogP:   1.685
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.018
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.877
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   2.0 Rigid Bonds:   18.0
TPSA:   96.22
?
Topological Polar Surface Area.
 H-Bond Acceptor:   6.0
H-Bond Donor:   3.0 Rings:   3.0
Heavy Atoms:   6.0

MedChem Properties

QED Drug-Likeness Score:   0.782 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.116 Fsp3:   0.188
MCE-18:   57.789
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Rejected GSK Rule:   Rejected
Golden Triangle Rule:   Rejected BMS Rule:   1
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.497 Fluc inhibitor:   0.591
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.242
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.274
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.368 Promiscuous compounds:   0.263

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.454 MDCK Permeability:   -4.795
Pgp-inhibitor:   0.788 Pgp-substrate:   0.232
PAMPA:   0.155
?
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):   0.005
20% Bioavailability (F20%):   0.019 30% Bioavailability (F30%):   0.476
50% Bioavailability (F50%):   0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.001 MRP1:   0.447
Plasma Protein Binding (PPB):   91.698% Volume Distribution (VD):   0.037
Fu: 9.446%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.999
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.931
BSEP inhibitor:   0.777

ADMET: Metabolism

CYP1A2-inhibitor:   0.942 CYP1A2-substrate:   0.001
CYP2C19-inhibitor:   0.169 CYP2C19-substrate:   0.001
CYP2C9-inhibitor:   0.897 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.502 CYP2D6-substrate:   0.08
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.076
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.241
HLM stability:   0.107
?
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):  9.964 Half-life (T1/2):  1.653

ADMET: Toxicity

hERG Blockers:  0.107 hERG Blockers (10um):  0.44
Human Hepatotoxicity (H-HT):  0.582 Drug-induced Liver Injury (DILI):  0.498
AMES Toxicity:  0.611 Rat Oral Acute Toxicity:  0.258
Maximum Recommended Daily Dose:  0.437 Skin Sensitization:  0.822
Carcinogencity:  0.296 Eye Corrosion:  0.01
Eye Irritation:  0.943 Respiratory Toxicity:  0.71
Drug-induced Neurotoxicity:  0.333 Ototoxicity:  0.49
Hematotoxicity:  0.251 Drug-induced Nephrotoxicity:  0.571
Genotoxicity:  0.932 RPMI-8226 Immunitoxicity:  0.143
A549 Cytotoxicity:  0.296 Hek293 Cytotoxicity:  0.545
BCF:   0.996
?
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:   3.665
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.576
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.896
?
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
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. stem wood n.a. DOI[10.1021/np100247r]
NPO33456 inula viscosa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[10217718]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10395501]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10425140]
NPO2166 Ajania fruticulosa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[10425142]
NPO24176 Streptomyces fradiae Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10757717]
NPO23281 Aplysinella rhax Species Aplysinellidae Eukaryota n.a. n.a. n.a. PMID[10757728]
NPO18509 Fissistigma oldhamii Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10978218]
NPO24219 Erylus nobilis Species n.a. n.a. n.a. n.a. n.a. PMID[11421740]
NPO24219 Erylus nobilis Species n.a. n.a. n.a. n.a. n.a. PMID[11908993]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[11914965]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[12350165]
NPO17823 Lycium chinense Species Solanaceae Eukaryota fruits n.a. n.a. PMID[12467621]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. Okinawan, Japan n.a. PMID[14695804]
NPO27122 Plumbago scandens Species Plumbaginaceae Eukaryota n.a. root n.a. PMID[14762525]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[15332859]
NPO6333 Annona glabra Species Annonaceae Eukaryota Fruits n.a. n.a. PMID[15568797]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. root n.a. PMID[16212233]
NPO15538 Eucalyptus citriodora Species Myrtaceae Eukaryota Leaves the campus of Panjab University, Chandigarh, India PMID[16989303]
NPO18509 Fissistigma oldhamii Species Annonaceae Eukaryota stem n.a. n.a. PMID[17081761]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[17407351]
NPO23281 Aplysinella rhax Species Aplysinellidae Eukaryota n.a. n.a. n.a. PMID[17827010]
NPO20637 Piper acutifolium Species Piperaceae Eukaryota n.a. leaf n.a. PMID[18712933]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. PMID[20488581]
NPO6333 Annona glabra Species Annonaceae Eukaryota stem Taipei Botanical Garden, Taipei, Taiwan, China 2006-MAR PMID[20828184]
NPO23499 Carpesium faberi Species Asteraceae Eukaryota whole plant Changshou County, Chongqing, China 2008-Aug PMID[21109433]
NPO27261 Carica papaya Species Caricaceae Eukaryota n.a. n.a. n.a. PMID[22305790]
NPO17823 Lycium chinense Species Solanaceae Eukaryota root bark n.a. n.a. PMID[23282106]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota Roots n.a. n.a. PMID[24054487]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota roots n.a. n.a. PMID[24412339]
NPO15538 Eucalyptus citriodora Species Myrtaceae Eukaryota Essential oil n.a. n.a. PMID[24641242]
NPO6333 Annona glabra Species Annonaceae Eukaryota fruits n.a. n.a. PMID[25499882]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[25987373]
NPO17823 Lycium chinense Species Solanaceae Eukaryota Root Bark n.a. n.a. PMID[26982999]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[27116034]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[29667821]
NPO7252 Sonchus oleraceus Species Asteraceae Eukaryota n.a. Molise Region, Italy Autumn 2018 PMID[32803719]
NPO7252 Sonchus oleraceus Species Asteraceae Eukaryota n.a. Molise Region, Italy Spring 2019 PMID[32803719]
NPO7252 Sonchus oleraceus Species Asteraceae Eukaryota n.a. Molise Region, Italy PMID[32803719]
NPO7252 Sonchus oleraceus Species Asteraceae Eukaryota n.a The rural area of Viçosa, State of Minas Gerais (MG), Brazil Adult stage PMID[35282307]
NPO27261 Carica papaya Species Caricaceae Eukaryota n.a. n.a. n.a. PMID[36235241]
NPO25864 Kunzea ericoides Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[38370080]
NPO14267 Seseli tortuosum Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[38475524]
NPO7252 Sonchus oleraceus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[38931144]
NPO27261 Carica papaya Species Caricaceae Eukaryota n.a. n.a. n.a. PMID[38986200]
NPO27457 Eupatorium capillifolium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[6790676]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[7807132]
NPO17823 Lycium chinense Species Solanaceae Eukaryota fruits n.a. n.a. PMID[9090870]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[9584397]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[9599260]
NPO27261 Carica papaya Species Caricaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO24176 Streptomyces fradiae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO27261 Carica papaya Species Caricaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7252 Sonchus oleraceus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21625 Bidens tripartita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2166 Ajania fruticulosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8566 Astragalus curvicarpus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1715 Eucalyptus radiata Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2901 Ilex taubertiana Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO247 Urceolaria bryophila Species Trichodinidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23739 Staehelina fruticosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21827 Albatrellus caeruleoporus Species Albatrellaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO738 Dahlstedtia pentaphylla Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16043 Centaurea musimomum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23281 Aplysinella rhax Species Aplysinellidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18440 Blepharostoma trichophyllum Species Pseudolepicoleaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23318 Aconitum palmatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18509 Fissistigma oldhamii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27457 Eupatorium capillifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24005 Mytilus galloprovincialis Species Mytilidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25003 Sorocea bonplandii Species Moraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24219 Erylus nobilis Species n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO5782 Aniba rosaeodora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27445 Artemisia filifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23545 Vellozia streptophylla Species Velloziaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18976 Centaurea arbutifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22143 Genista sessilifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14267 Seseli tortuosum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12429 Acicarpha tribuloides Species Calyceraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20998 Machaerium kuhlmannii Species Dolichopodidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24090 Aplysilla rosea Species Darwinellidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25767 Aplysia juliana Species Aplysiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23211 Xyris indica Species Xyridaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27261 Carica papaya Species Caricaceae Eukaryota n.a. n.a. Database[FooDB]
NPO27261 Carica papaya Species Caricaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO27261 Carica papaya Species Caricaceae Eukaryota Latex Exudate n.a. n.a. Database[FooDB]
NPO27261 Carica papaya Species Caricaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO27261 Carica papaya Species Caricaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO27261 Carica papaya Species Caricaceae Eukaryota n.a. n.a. Database[FooDB]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27261 Carica papaya Species Caricaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22455 Corydalis sewerzowi Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14267 Seseli tortuosum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21625 Bidens tripartita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27261 Carica papaya Species Caricaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15538 Eucalyptus citriodora Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27261 Carica papaya Species Caricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22455 Corydalis sewerzowi Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25003 Sorocea bonplandii Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18440 Blepharostoma trichophyllum Species Pseudolepicoleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14267 Seseli tortuosum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21625 Bidens tripartita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14267 Seseli tortuosum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27261 Carica papaya Species Caricaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24090 Aplysilla rosea Species Darwinellidae Eukaryota n.a. Austrila n.a. Database[Title]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12429 Acicarpha tribuloides Species Calyceraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23211 Xyris indica Species Xyridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23413 Crematogaster africana Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23884 Hippobroma longiflora Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23610 Aconitum tianschanicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7252 Sonchus oleraceus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23792 Gomphostemma parviflorum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24408 Ariocarpus fissuratus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23961 Scytonema ocellatum Species Scytonemataceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO22143 Genista sessilifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5573 Oxycoccus quadripetalus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO24176 Streptomyces fradiae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO27281 Grindelia spathulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24132 Euphausia superba Species Euphausiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2166 Ajania fruticulosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27122 Plumbago scandens Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23739 Staehelina fruticosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23114 Cacalia robusta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27457 Eupatorium capillifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15538 Eucalyptus citriodora Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24445 Arbacia pustulosa Species Arbaciidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24005 Mytilus galloprovincialis Species Mytilidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8566 Astragalus curvicarpus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18509 Fissistigma oldhamii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20998 Machaerium kuhlmannii Species Dolichopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23499 Carpesium faberi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22595 Trapa bicornis Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25864 Kunzea ericoides Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19535 Senecio zoellneri Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20637 Piper acutifolium Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23364 Lambertella corni Species Rutstroemiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24249 Codonopsis cordifolioidea Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23281 Aplysinella rhax Species Aplysinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24090 Aplysilla rosea Species Darwinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23696 Solanum diflorum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27261 Carica papaya Species Caricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24219 Erylus nobilis Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO13127 Vallaris heynei Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8593 Zygosaccharomyces rouxii Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18976 Centaurea arbutifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23459 Onoseris alata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21827 Albatrellus caeruleoporus Species Albatrellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23043 Cryptolestes pusillus Species Laemophloeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22324 Erium villosum Species Pseudococcidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26067 Acacia sutherlandii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25003 Sorocea bonplandii Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5782 Aniba rosaeodora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24048 Cladonia pityrea Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18440 Blepharostoma trichophyllum Species Pseudolepicoleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16043 Centaurea musimomum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2901 Ilex taubertiana Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1715 Eucalyptus radiata Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17737 Lepidorhinus squamosus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO22455 Corydalis sewerzowi Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23318 Aconitum palmatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23920 Amanita pseudoporphyria Species Amanitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24290 Claviceps microcephala Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23545 Vellozia streptophylla Species Velloziaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23834 Chlamydomonas allensworthii Species Chlamydomonadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21625 Bidens tripartita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO738 Dahlstedtia pentaphylla Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25767 Aplysia juliana Species Aplysiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO247 Urceolaria bryophila Species Trichodinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27445 Artemisia filifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23377 Stephanitis pyrioides Species Tingidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19046 Pyrenula pseudobufonia Species Pyrenulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15589 Alcyonium digitatum Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23438 Berchemia formosana Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14267 Seseli tortuosum Species Apiaceae 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
NPT32 Organism Mus musculus Mus musculus Inhibition = 78.0 % PMID[10217718]
NPT32 Organism Mus musculus Mus musculus Inhibition = 3.0 % PMID[10217718]





 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 NPC176869 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 NPC3779
0.8125 Intermediate Similarity NPC122828
0.72 Intermediate Similarity NPC62290
0.72 Intermediate Similarity NPC142731
0.72 Intermediate Similarity NPC326506
0.6604 Remote Similarity NPC44721
0.6604 Remote Similarity NPC211466
0.6604 Remote Similarity NPC605332
0.66 Remote Similarity NPC1940
0.6415 Remote Similarity NPC201837
0.6226 Remote Similarity NPC484336
0.6226 Remote Similarity NPC484337
0.6111 Remote Similarity NPC329203
0.6111 Remote Similarity NPC222342
0.6034 Remote Similarity NPC326037
0.6034 Remote Similarity NPC13858
0.6034 Remote Similarity NPC20907
0.5926 Remote Similarity NPC4152
0.5893 Remote Similarity NPC36835
0.5893 Remote Similarity NPC246162
0.5893 Remote Similarity NPC9743
0.5893 Remote Similarity NPC260491
0.5893 Remote Similarity NPC61506
0.5893 Remote Similarity NPC240476
0.5893 Remote Similarity NPC602118
0.5741 Remote Similarity NPC148011
0.5714 Remote Similarity NPC471500
0.569 Remote Similarity NPC320825
0.569 Remote Similarity NPC52530
0.5636 Remote Similarity NPC279417
0.5636 Remote Similarity NPC49130
0.5614 Remote Similarity NPC250922
0.5614 Remote Similarity NPC609065
0.5593 Remote Similarity NPC484335
0.5593 Remote Similarity NPC600886
0.5536 Remote Similarity NPC246328
0.5536 Remote Similarity NPC27532
0.5522 Remote Similarity NPC163191
0.5455 Remote Similarity NPC21835
0.5455 Remote Similarity NPC476182
0.5439 Remote Similarity NPC263449
0.5424 Remote Similarity NPC244250
0.5397 Remote Similarity NPC217706
0.537 Remote Similarity NPC31704
0.5333 Remote Similarity NPC112418
0.5323 Remote Similarity NPC271741
0.5263 Remote Similarity NPC325028
0.5263 Remote Similarity NPC256346
0.5263 Remote Similarity NPC19721
0.5263 Remote Similarity NPC606550
0.5254 Remote Similarity NPC611035
0.5179 Remote Similarity NPC263670
0.5172 Remote Similarity NPC306607
0.5172 Remote Similarity NPC308992
0.5152 Remote Similarity NPC610035
0.5088 Remote Similarity NPC208176
0.5085 Remote Similarity NPC310135
0.5082 Remote Similarity NPC123544
0.5079 Remote Similarity NPC262038
0.5079 Remote Similarity NPC319910

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC176869 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