Natural Product: NPC66812

Natural Product IDNPC66812
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 UNYNVICDCJHOPO-SCSAIBSYSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID 12799212
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001983] Dihydrofurans
        • [CHEMONTID:0001982] Furanones
          • [CHEMONTID:0002223] Butenolides

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 UNYNVICDCJHOPO-SCSAIBSYSA-N
Standard InCHI InChI=1S/C6H8O3/c1-3-4(2)9-6(8)5(3)7/h4,7H,1-2H3/t4-/m1/s1
SMILES CC1=C(C(=O)O[C@@H]1C)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   128.05 Volume:   124.874
?
Van der Waals volume.
Dense:   1.025 LogP:   0.38
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   0.53
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -0.649
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   0.0 Rigid Bonds:   6.0
TPSA:   46.53
?
Topological Polar Surface Area.
 H-Bond Acceptor:   3.0
H-Bond Donor:   1.0 Rings:   1.0
Heavy Atoms:   3.0

MedChem Properties

QED Drug-Likeness Score:   0.49 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.575 Fsp3:   0.5
MCE-18:   15.556
?
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:   0.097 Fluc inhibitor:   0.008
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.117
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.032
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.997 Promiscuous compounds:   0.145

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.541 MDCK Permeability:   -4.462
Pgp-inhibitor:   0.181 Pgp-substrate:   0.594
PAMPA:   0.615
?
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):   0.2
20% Bioavailability (F20%):   0.682 30% Bioavailability (F30%):   0.877
50% Bioavailability (F50%):   0.913

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.241 MRP1:   0.957
Plasma Protein Binding (PPB):   51.707% Volume Distribution (VD):   -0.278
Fu: 43.795%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.9
OATP1B3 inhibitor:   0.941 BCRP inhibitor:   0.21
BSEP inhibitor:   0.343

ADMET: Metabolism

CYP1A2-inhibitor:   0.395 CYP1A2-substrate:   0.857
CYP2C19-inhibitor:   0.236 CYP2C19-substrate:   0.201
CYP2C9-inhibitor:   0.063 CYP2C9-substrate:   0.003
CYP2D6-inhibitor:   0.161 CYP2D6-substrate:   0.056
CYP3A4-inhibitor:   0.944 CYP3A4-substrate:   0.999
CYP2B6-substrate:   0.003 CYP2C8-inhibitor:   0.515
HLM stability:   0.745
?
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):  7.101 Half-life (T1/2):  1.934

ADMET: Toxicity

hERG Blockers:  0.012 hERG Blockers (10um):  0.101
Human Hepatotoxicity (H-HT):  0.617 Drug-induced Liver Injury (DILI):  0.905
AMES Toxicity:  0.748 Rat Oral Acute Toxicity:  0.49
Maximum Recommended Daily Dose:  0.273 Skin Sensitization:  0.991
Carcinogencity:  0.817 Eye Corrosion:  0.896
Eye Irritation:  0.993 Respiratory Toxicity:  0.47
Drug-induced Neurotoxicity:  0.614 Ototoxicity:  0.253
Hematotoxicity:  0.427 Drug-induced Nephrotoxicity:  0.888
Genotoxicity:  0.888 RPMI-8226 Immunitoxicity:  0.043
A549 Cytotoxicity:  0.052 Hek293 Cytotoxicity:  0.045
BCF:   0.465
?
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:   2.964
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.28
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.577
?
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
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. Nigeria(latitude 80°N and longitude 4°E) 2005; 2006 DOI[10.1002/ejlt.201000080]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11240-015-0761-z]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11306-010-0259-y]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11306-014-0638-x]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11746-997-0093-1]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s12010-013-0354-4]
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.bse.2004.02.008]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jarmap.2018.11.004]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.phytol.2008.07.007]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seeds Plovdiv, Plovdiv region in South Bulgaria DOI[10.1051/CTV/20163101031]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1055/S-2006-958077]
NPO947 Rauvolfia vomitoria Species Apocynaceae Eukaryota n.a. n.a. n.a. DOI[10.1080/01496395.2011.635623]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1186/s40064-015-0831-z]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1501/Tarimbil_0000001065]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[11170689]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. leaf n.a. PMID[11312782]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. fruit n.a. PMID[11312782]
NPO15659 Zanthoxylum tetraspermum Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[11324918]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[11408943]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. fruit n.a. PMID[12105962]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[14600382]
NPO15063 Leathesia nana Species Chordariaceae Eukaryota n.a. n.a. n.a. PMID[15497936]
NPO9516 Gnetum latifolium Species Gnetaceae Eukaryota stem bark Veikabu bridge along the Hiritano highway 40 km from Port Moresby, Papua New Guinea 1998-FEB PMID[16038553]
NPO6160 Vaccinium oxycoccos Species Ericaceae Eukaryota n.a. fruit n.a. PMID[16417304]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. Esuela Tecnica Superior de Ingenieros Agrónomos de Albacete 2007 PMID[19256538]
NPO11917 Asterospicularia laurae Species Xeniidae Eukaryota n.a. n.a. n.a. PMID[19863101]
NPO17094 Sinularia depressa Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[20121250]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[20826702]
NPO4181 Pseudoalteromonas luteoviolacea Species Pseudoalteromonadaceae Bacteria n.a. n.a. n.a. PMID[20973551]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21800857]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[22537213]
NPO17094 Sinularia depressa Species Alcyoniidae Eukaryota n.a. Hainan soft coral n.a. PMID[23357636]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[23759170]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Stalks n.a. n.a. PMID[24521157]
NPO13847 Streptomyces avermectinius Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25611131]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota Twigs n.a. n.a. PMID[25894905]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota Twigs n.a. n.a. PMID[28358502]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seeds Benedictine Pannonhalma Archabbey, Hungary PMID[29803478]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[31433178]
NPO7562 Premna odorata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[32521614]
NPO16857 Hypericum laricifolium Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[36365414]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[37446586]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[37570937]
NPO947 Rauvolfia vomitoria Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[38416335]
NPO13847 Streptomyces avermectinius Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[464561]
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[7513747]
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[7561895]
NPO17544 Acacia adunca Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17169 Adiantum lunulatum Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16611 Alstonia spathulata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17865 Amathia pinnata Species Vesiculariidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15552 Anacystis montana n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO10989 Annona cornifolia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15803 Artemisia assoana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11917 Asterospicularia laurae Species Xeniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17702 Astragalus sempervirens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14859 Bishovia boliviensis n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO4325 Blastochloris viridis Species Hyphomicrobiaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO3964 Calostephane divaricata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6881 Caragana aurantiaca Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8506 Cotyledon secunda Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17472 Drechslera avenae Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16089 Dumortiera hirsuta Species Dumortieraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12703 Eucalyptus melliodora Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9516 Gnetum latifolium Species Gnetaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13407 Goniothalamus malayanus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15467 Hedysarum connatum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15227 Helipterum roseum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16857 Hypericum laricifolium Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10417 Ipomoea digitata Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17242 Laurencia spectabilis Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15063 Leathesia nana Species Chordariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16369 Lepisorus ussuriensis Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14395 Lysimachia mauritiana Species Primulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17786 Marrubium anisodon Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16493 Nasutitermes ephratae Species Termitoidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18022 Naucleopsis ternstroemiiflora Species Moraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17400 Peltostigma guatemalense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16731 Phoebe pittieri Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7562 Premna odorata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4181 Pseudoalteromonas luteoviolacea Species Pseudoalteromonadaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO947 Rauvolfia vomitoria Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2507 Rumex maritimus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21724 Sabina sargentii n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO11538 Salvia syriaca Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13167 Scutellaria amoena Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17094 Sinularia depressa Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11641 Solanum laxum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13847 Streptomyces avermectinius Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6160 Vaccinium oxycoccos Species Ericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17633 Viguiera incana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17942 Wikstroemia retusa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15659 Zanthoxylum tetraspermum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Root Essent. Oil n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. Database[FooDB]
NPO6160 Vaccinium oxycoccos Species Ericaceae Eukaryota n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Roots n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Fruits n.a. Database[FooDB]
NPO13167 Scutellaria amoena Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO947 Rauvolfia vomitoria Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO6160 Vaccinium oxycoccos Species Ericaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO947 Rauvolfia vomitoria Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13167 Scutellaria amoena Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16857 Hypericum laricifolium Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11641 Solanum laxum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9516 Gnetum latifolium Species Gnetaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13167 Scutellaria amoena Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2507 Rumex maritimus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10417 Ipomoea digitata Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12703 Eucalyptus melliodora Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17094 Sinularia depressa Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21724 Sabina sargentii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO13167 Scutellaria amoena Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15552 Anacystis montana n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO9516 Gnetum latifolium Species Gnetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16857 Hypericum laricifolium Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3964 Calostephane divaricata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16611 Alstonia spathulata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16089 Dumortiera hirsuta Species Dumortieraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16493 Nasutitermes ephratae Species Termitoidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17400 Peltostigma guatemalense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14685 Swertia franchetiana Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17633 Viguiera incana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16369 Lepisorus ussuriensis Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17169 Adiantum lunulatum Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13847 Streptomyces avermectinius Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17942 Wikstroemia retusa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO947 Rauvolfia vomitoria Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15227 Helipterum roseum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15803 Artemisia assoana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14395 Lysimachia mauritiana Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15063 Leathesia nana Species Chordariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4181 Pseudoalteromonas luteoviolacea Species Pseudoalteromonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO7562 Premna odorata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15659 Zanthoxylum tetraspermum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11917 Asterospicularia laurae Species Xeniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13407 Goniothalamus malayanus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6160 Vaccinium oxycoccos Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18022 Naucleopsis ternstroemiiflora Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14859 Bishovia boliviensis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO17242 Laurencia spectabilis Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16731 Phoebe pittieri Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6881 Caragana aurantiaca Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17544 Acacia adunca Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11641 Solanum laxum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11538 Salvia syriaca Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4325 Blastochloris viridis Species Hyphomicrobiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17865 Amathia pinnata Species Vesiculariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8506 Cotyledon secunda Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10989 Annona cornifolia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17786 Marrubium anisodon Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17702 Astragalus sempervirens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15467 Hedysarum connatum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17472 Drechslera avenae Species Pleosporaceae 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 NPC66812 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 NPC327103

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC66812 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