Natural Product: NPC231773

Natural Product IDNPC231773
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 DANYIYRPLHHOCZ-UHFFFAOYSA-M
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID 25202697
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0002585] O-methylated flavonoids
          • [CHEMONTID:0002596] 4'-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 DANYIYRPLHHOCZ-UHFFFAOYSA-M
Standard InCHI InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-8,17-18H,1H3/p-1
SMILES COc1ccc(cc1)c1cc(=O)c2c(cc(cc2o1)[O-])O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   284.07 Volume:   282.482
?
Van der Waals volume.
Dense:   1.006 LogP:   2.994
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.89
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.762
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   2.0 Rigid Bonds:   18.0
TPSA:   79.9
?
Topological Polar Surface Area.
 H-Bond Acceptor:   5.0
H-Bond Donor:   2.0 Rings:   3.0
Heavy Atoms:   5.0

MedChem Properties

QED Drug-Likeness Score:   0.756 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.131 Fsp3:   0.062
MCE-18:   17.0
?
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:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.549 Fluc inhibitor:   0.997
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.945
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.774
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.574 Promiscuous compounds:   0.891

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.911 MDCK Permeability:   -4.798
Pgp-inhibitor:   0.078 Pgp-substrate:   0.529
PAMPA:   0.175
?
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):   0.07
20% Bioavailability (F20%):   0.543 30% Bioavailability (F30%):   0.854
50% Bioavailability (F50%):   0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.019 MRP1:   0.699
Plasma Protein Binding (PPB):   97.581% Volume Distribution (VD):   -0.242
Fu: 1.862%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.728
OATP1B3 inhibitor:   0.97 BCRP inhibitor:   0.952
BSEP inhibitor:   0.684

ADMET: Metabolism

CYP1A2-inhibitor:   0.991 CYP1A2-substrate:   0.21
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.022
CYP2C9-inhibitor:   0.958 CYP2C9-substrate:   0.998
CYP2D6-inhibitor:   1.0 CYP2D6-substrate:   0.999
CYP3A4-inhibitor:   0.006 CYP3A4-substrate:   0.155
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.957
?
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):  5.282 Half-life (T1/2):  0.926

ADMET: Toxicity

hERG Blockers:  0.126 hERG Blockers (10um):  0.518
Human Hepatotoxicity (H-HT):  0.427 Drug-induced Liver Injury (DILI):  0.898
AMES Toxicity:  0.707 Rat Oral Acute Toxicity:  0.462
Maximum Recommended Daily Dose:  0.845 Skin Sensitization:  0.44
Carcinogencity:  0.836 Eye Corrosion:  0.427
Eye Irritation:  0.996 Respiratory Toxicity:  0.852
Drug-induced Neurotoxicity:  0.084 Ototoxicity:  0.078
Hematotoxicity:  0.1 Drug-induced Nephrotoxicity:  0.055
Genotoxicity:  0.941 RPMI-8226 Immunitoxicity:  0.068
A549 Cytotoxicity:  0.26 Hek293 Cytotoxicity:  0.71
BCF:   1.269
?
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:   3.897
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.589
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.134
?
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
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2009.03.042]
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]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[10336650]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota flowers bought from a drugstore in Beijing n.a. PMID[10514305]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[11551759]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. flower n.a. PMID[12130858]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota flower buds n.a. n.a. PMID[14738377]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[15679315]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[16252923]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. n.a. n.a. PMID[17548953]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[17624889]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18611049]
NPO1960 Lygodium japonicum Species Lygodiaceae Eukaryota n.a. n.a. n.a. PMID[18619266]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18768384]
NPO21782 Nuxia sphaerocephala Species Stilbaceae Eukaryota leaves n.a. n.a. PMID[19299148]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[19476340]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. whole plant n.a. PMID[21214467]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota flowers n.a. n.a. PMID[21524582]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[21912858]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[22111577]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. flower n.a. PMID[22166201]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[23790907]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers Tongxiang, China n.a. PMID[24621197]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. n.a. n.a. PMID[24675423]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. Bako, Ethiopia PMID[24926420]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. Enemore, Ethiopia PMID[24926420]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. Gedo, Ethiopia PMID[24926420]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. Holleta, Ethiopia PMID[24926420]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[24948953]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[25564559]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[26099993]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[27128895]
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]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[29154541]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota Resinous Wood n.a. n.a. PMID[29227647]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[29400471]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[30384263]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Aerial Parts n.a. n.a. PMID[30726671]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[37631012]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[38354824]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[38792158]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[39199155]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[8158164]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. inflorescence n.a. PMID[8158164]
NPO16841 Elsholtzia bodinieri Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8300 Apis mellifera ligustica Species Apidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO30745 Chrysanthemum morifolium 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]
NPO25890 Herba cirsii japonici n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO23795 Herba seu radix cirsii japonici n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO19689 Radix cirsii japonici Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1960 Lygodium japonicum Species Lygodiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24062 Radix pseudostellariae Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22913 Ajuga forrestii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11697 Cirsium setosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3392 Agastache rugosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16963 Fructus leonuri n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21782 Nuxia sphaerocephala Species Stilbaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3392 Agastache rugosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16963 Fructus leonuri n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO1960 Lygodium japonicum Species Lygodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17556 Verbascum lychnites Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11697 Cirsium setosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22913 Ajuga forrestii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21782 Nuxia sphaerocephala Species Stilbaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8300 Apis mellifera ligustica Species Apidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25890 Herba cirsii japonici n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24062 Radix pseudostellariae Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19689 Radix cirsii japonici Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25451 Lysimachia paridiformis Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16963 Fructus leonuri n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO3392 Agastache rugosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23795 Herba seu radix cirsii japonici n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO17556 Verbascum lychnites Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11697 Cirsium setosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1960 Lygodium japonicum Species Lygodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16841 Elsholtzia bodinieri Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22913 Ajuga forrestii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21782 Nuxia sphaerocephala Species Stilbaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1960 Lygodium japonicum Species Lygodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22913 Ajuga forrestii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17556 Verbascum lychnites Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13857 Mentha canadensis Species Lamiaceae 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]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11697 Cirsium setosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16841 Elsholtzia bodinieri Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11697 Cirsium setosum 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]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22913 Ajuga forrestii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21782 Nuxia sphaerocephala Species Stilbaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25451 Lysimachia paridiformis Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14558 Aquilaria sinensis 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

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 NPC231773 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
0.8571 High Similarity NPC29353
0.717 Intermediate Similarity NPC127447
0.7037 Intermediate Similarity NPC231772
0.7037 Intermediate Similarity NPC57030
0.7037 Intermediate Similarity NPC234133
0.7037 Intermediate Similarity NPC145379
0.6964 Remote Similarity NPC195202
0.6964 Remote Similarity NPC223579
0.6909 Remote Similarity NPC603662
0.6852 Remote Similarity NPC52611
0.6607 Remote Similarity NPC108406
0.6562 Remote Similarity NPC248739
0.6545 Remote Similarity NPC156222
0.6462 Remote Similarity NPC601984
0.6429 Remote Similarity NPC33265
0.6429 Remote Similarity NPC184136
0.6429 Remote Similarity NPC48479
0.6364 Remote Similarity NPC158027
0.6271 Remote Similarity NPC137062
0.6271 Remote Similarity NPC610914
0.6269 Remote Similarity NPC14606
0.625 Remote Similarity NPC600177
0.6176 Remote Similarity NPC121649
0.614 Remote Similarity NPC22519
0.6102 Remote Similarity NPC177298
0.6087 Remote Similarity NPC18699
0.6087 Remote Similarity NPC95090
0.6087 Remote Similarity NPC27408
0.6 Remote Similarity NPC181712
0.5965 Remote Similarity NPC274327
0.5965 Remote Similarity NPC262094
0.5882 Remote Similarity NPC600396
0.5873 Remote Similarity NPC602829
0.5862 Remote Similarity NPC176775
0.5862 Remote Similarity NPC266597
0.5862 Remote Similarity NPC604085
0.5862 Remote Similarity NPC604462
0.5857 Remote Similarity NPC205026
0.5833 Remote Similarity NPC124784
0.5818 Remote Similarity NPC604293
0.5797 Remote Similarity NPC159707
0.5797 Remote Similarity NPC186227
0.5753 Remote Similarity NPC80188
0.5753 Remote Similarity NPC608742
0.5714 Remote Similarity NPC101294
0.569 Remote Similarity NPC275722
0.569 Remote Similarity NPC239128
0.5676 Remote Similarity NPC220169
0.5667 Remote Similarity NPC69394
0.5667 Remote Similarity NPC212678
0.5667 Remote Similarity NPC328119
0.5634 Remote Similarity NPC601565
0.5614 Remote Similarity NPC14958
0.5593 Remote Similarity NPC18260
0.5593 Remote Similarity NPC198826
0.5593 Remote Similarity NPC120163
0.5588 Remote Similarity NPC604322
0.5574 Remote Similarity NPC160951
0.5574 Remote Similarity NPC283600
0.5574 Remote Similarity NPC52005
0.5574 Remote Similarity NPC12200
0.5556 Remote Similarity NPC265624
0.5507 Remote Similarity NPC150908
0.5507 Remote Similarity NPC603508
0.55 Remote Similarity NPC78913
0.5439 Remote Similarity NPC2771
0.5429 Remote Similarity NPC303485
0.5424 Remote Similarity NPC306821
0.5424 Remote Similarity NPC187498
0.5405 Remote Similarity NPC55443
0.5397 Remote Similarity NPC295036
0.5352 Remote Similarity NPC194593
0.5333 Remote Similarity NPC250266
0.5333 Remote Similarity NPC483773
0.5312 Remote Similarity NPC485299
0.5254 Remote Similarity NPC293183
0.5254 Remote Similarity NPC75279
0.525 Remote Similarity NPC22062
0.525 Remote Similarity NPC473634
0.525 Remote Similarity NPC138811
0.5246 Remote Similarity NPC25270
0.5246 Remote Similarity NPC162313
0.5246 Remote Similarity NPC256283
0.5224 Remote Similarity NPC470402
0.5167 Remote Similarity NPC241498
0.5167 Remote Similarity NPC125887
0.5161 Remote Similarity NPC200740
0.5161 Remote Similarity NPC270620
0.5161 Remote Similarity NPC166753
0.5161 Remote Similarity NPC255350
0.5147 Remote Similarity NPC183
0.5139 Remote Similarity NPC272064
0.5135 Remote Similarity NPC186807
0.5135 Remote Similarity NPC602537
0.5132 Remote Similarity NPC22832
0.5132 Remote Similarity NPC243930
0.5122 Remote Similarity NPC46202
0.5082 Remote Similarity NPC110070
0.5082 Remote Similarity NPC32557
0.5082 Remote Similarity NPC62536
0.5082 Remote Similarity NPC120464
0.5082 Remote Similarity NPC276409
0.5082 Remote Similarity NPC601901
0.5082 Remote Similarity NPC610380
0.5079 Remote Similarity NPC236769
0.507 Remote Similarity NPC600972
0.5068 Remote Similarity NPC58053
0.5068 Remote Similarity NPC215203
0.5067 Remote Similarity NPC27942
0.5065 Remote Similarity NPC607707

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC231773 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
0.5161 Remote Similarity NPD2801 Pre-clinical

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