Natural Product: NPC210632

Natural Product IDNPC210632
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 FOMYLMGOSTVYEE-LEENXRGASA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID 5319985
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0003531] Flavonoid-3-O-glycosides

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 FOMYLMGOSTVYEE-LEENXRGASA-N
Standard InCHI InChI=1S/C28H24O17/c29-10-5-11(30)18-16(6-10)43-25(8-1-12(31)19(35)13(32)2-8)26(22(18)38)45-28-24(40)23(39)21(37)17(44-28)7-42-27(41)9-3-14(33)20(36)15(34)4-9/h1-6,17,21,23-24,28-37,39-40H,7H2/t17-,21+,23+,24-,28+/m1/s1
SMILES c1c(cc(c(c1O)O)O)c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](COC(=O)c2cc(c(c(c2)O)O)O)O1)O)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   632.1 Volume:   567.858
?
Van der Waals volume.
Dense:   1.113 LogP:   0.729
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   0.721
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.476
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   7.0 Rigid Bonds:   31.0
TPSA:   297.5
?
Topological Polar Surface Area.
 H-Bond Acceptor:   17.0
H-Bond Donor:   11.0 Rings:   5.0
Heavy Atoms:   17.0

MedChem Properties

QED Drug-Likeness Score:   0.1 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   4.449 Fsp3:   0.214
MCE-18:   118.588
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Accepted
Pfizer Rule:   Rejected GSK Rule:   Accepted
Golden Triangle Rule:   Accepted BMS Rule:   1
Chelating Alert:   1 PAINS Alert:   1
Colloidal aggregators:   0.763 Fluc inhibitor:   0.199
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.875
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.648
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.221 Promiscuous compounds:   0.984

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -6.748 MDCK Permeability:   -4.743
Pgp-inhibitor:   0.0 Pgp-substrate:   0.101
PAMPA:   0.999
?
The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).
 Human Intestinal Absorption (HIA):   0.0
20% Bioavailability (F20%):   0.913 30% Bioavailability (F30%):   0.998
50% Bioavailability (F50%):   1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.0 MRP1:   0.995
Plasma Protein Binding (PPB):   81.743% Volume Distribution (VD):   -0.017
Fu: 15.903%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.974
OATP1B3 inhibitor:   0.997 BCRP inhibitor:   0.995
BSEP inhibitor:   0.55

ADMET: Metabolism

CYP1A2-inhibitor:   0.011 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.017
CYP2C9-inhibitor:   0.0 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   1.0
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.092
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.99
?
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):  3.332 Half-life (T1/2):  4.168

ADMET: Toxicity

hERG Blockers:  0.011 hERG Blockers (10um):  0.902
Human Hepatotoxicity (H-HT):  0.073 Drug-induced Liver Injury (DILI):  0.931
AMES Toxicity:  0.542 Rat Oral Acute Toxicity:  0.07
Maximum Recommended Daily Dose:  0.833 Skin Sensitization:  1.0
Carcinogencity:  0.077 Eye Corrosion:  0.0
Eye Irritation:  0.968 Respiratory Toxicity:  0.08
Drug-induced Neurotoxicity:  0.0 Ototoxicity:  0.989
Hematotoxicity:  0.0 Drug-induced Nephrotoxicity:  0.0
Genotoxicity:  0.995 RPMI-8226 Immunitoxicity:  0.002
A549 Cytotoxicity:  1.0 Hek293 Cytotoxicity:  0.518
BCF:   0.602
?
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:   3.401
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.399
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.032
?
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
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Leaves n.a. n.a. PMID[12088434]
NPO22423 Microtropis fokienensis Species Celastraceae Eukaryota stem n.a. n.a. PMID[16643054]
NPO22423 Microtropis fokienensis Species Celastraceae Eukaryota leaves n.a. n.a. PMID[17125218]
NPO22423 Microtropis fokienensis Species Celastraceae Eukaryota n.a. root n.a. PMID[17315960]
NPO22423 Microtropis fokienensis Species Celastraceae Eukaryota roots n.a. n.a. PMID[17315960]
NPO138 Daphniphyllum paxianum Species Daphniphyllaceae Eukaryota n.a. n.a. n.a. PMID[17887722]
NPO22423 Microtropis fokienensis Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[18590313]
NPO22791 Astraeus pteridis Species Astraeaceae Eukaryota n.a. n.a. n.a. PMID[19067555]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[21707257]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota roots n.a. n.a. PMID[21911291]
NPO1346 Nerine bowdenii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[22312717]
NPO11877 Penicillium herquei Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26848504]
NPO8752 Xylaria cubensis Species Xylariaceae Eukaryota n.a. n.a. n.a. PMID[28802670]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[29726697]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[31675225]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[34443694]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[34770961]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[35631245]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[36840093]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[37020229]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[37226152]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[38257205]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[38370080]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[38381096]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[38695450]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[39407547]
NPO1831 Pseudodistoma arborescens Species Pseudodistomidae Eukaryota n.a. n.a. n.a. PMID[8450325]
NPO11877 Penicillium herquei Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[8609085]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6622 Artemisia klotzchiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9252 Adina sessilifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11657 Angelica lucida Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1697 Bitis gabonica Species Viperidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11934 Castanea vesca Species Fagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13472 Cotula cinerea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO138 Daphniphyllum paxianum Species Daphniphyllaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21255 Hymenoxys insignis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3995 Limonium sinense Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11823 Marine actinobacterium n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO6845 Mimusops caffra Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1346 Nerine bowdenii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14564 Oophaga pumilio Species Dendrobatidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11877 Penicillium herquei Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1831 Pseudodistoma arborescens Species Pseudodistomidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4969 Sesbania bispinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5735 Solidago serotina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9153 Sorbaria sorbifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11771 Strophanthus kombe Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8127 Veronica arvensis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8752 Xylaria cubensis Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23494 Centaurea linifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22423 Microtropis fokienensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5054 Limonium gmelinii Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4594 Vitellaria paradoxa Species Sapotaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4969 Sesbania bispinosa Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4594 Vitellaria paradoxa Species Sapotaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9153 Sorbaria sorbifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8127 Veronica arvensis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11771 Strophanthus kombe Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5054 Limonium gmelinii Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11771 Strophanthus kombe Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9153 Sorbaria sorbifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5054 Limonium gmelinii Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6622 Artemisia klotzchiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8127 Veronica arvensis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9153 Sorbaria sorbifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11771 Strophanthus kombe Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5054 Limonium gmelinii Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13472 Cotula cinerea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23954 Tridachia crispata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO24327 Machilus macrantha Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11877 Penicillium herquei Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8127 Veronica arvensis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5735 Solidago serotina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22791 Astraeus pteridis Species Astraeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14564 Oophaga pumilio Species Dendrobatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6845 Mimusops caffra Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11823 Marine actinobacterium n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO5054 Limonium gmelinii Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21255 Hymenoxys insignis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25848 Oscillochloris trichoides Species Oscillochloridaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11657 Angelica lucida Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3995 Limonium sinense Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22423 Microtropis fokienensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20604 Cneoridium dumosum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9153 Sorbaria sorbifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4594 Vitellaria paradoxa Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9252 Adina sessilifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO138 Daphniphyllum paxianum Species Daphniphyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4969 Sesbania bispinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6622 Artemisia klotzchiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23879 Serratula inermis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21956 Alyxia reinwardtii Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1831 Pseudodistoma arborescens Species Pseudodistomidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8752 Xylaria cubensis Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1697 Bitis gabonica Species Viperidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1346 Nerine bowdenii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11771 Strophanthus kombe Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11934 Castanea vesca Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23494 Centaurea linifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].



  NP Quantity Composition/Concentration

Organism ID Organism Name Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].



 Biological Activity

Molecular-level activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

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 NPC210632 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
0.9146 High Similarity NPC37668
0.8916 High Similarity NPC270448
0.8452 Intermediate Similarity NPC154741
0.8235 Intermediate Similarity NPC296018
0.7701 Intermediate Similarity NPC129264
0.7473 Intermediate Similarity NPC135831
0.7363 Intermediate Similarity NPC486577
0.7273 Intermediate Similarity NPC39834
0.7174 Intermediate Similarity NPC97119
0.7073 Intermediate Similarity NPC135599
0.7073 Intermediate Similarity NPC73855
0.7073 Intermediate Similarity NPC113968
0.7073 Intermediate Similarity NPC328940
0.7073 Intermediate Similarity NPC277174
0.7073 Intermediate Similarity NPC606877
0.6989 Remote Similarity NPC603079
0.6988 Remote Similarity NPC19388
0.6988 Remote Similarity NPC240431
0.6988 Remote Similarity NPC55786
0.6932 Remote Similarity NPC116864
0.6932 Remote Similarity NPC244776
0.6889 Remote Similarity NPC196127
0.6778 Remote Similarity NPC258044
0.6778 Remote Similarity NPC217387
0.6627 Remote Similarity NPC34531
0.6531 Remote Similarity NPC81042
0.6522 Remote Similarity NPC67326
0.6452 Remote Similarity NPC203259
0.6452 Remote Similarity NPC33054
0.6452 Remote Similarity NPC176740
0.6452 Remote Similarity NPC471725
0.6452 Remote Similarity NPC134532
0.6452 Remote Similarity NPC156869
0.6452 Remote Similarity NPC602582
0.6429 Remote Similarity NPC223426
0.6413 Remote Similarity NPC609888
0.6364 Remote Similarity NPC214621
0.6364 Remote Similarity NPC34267
0.6292 Remote Similarity NPC182121
0.6279 Remote Similarity NPC476771
0.6237 Remote Similarity NPC471079
0.6224 Remote Similarity NPC85751
0.6224 Remote Similarity NPC19240
0.6211 Remote Similarity NPC35167
0.6211 Remote Similarity NPC144097
0.6207 Remote Similarity NPC127546
0.6207 Remote Similarity NPC57625
0.6207 Remote Similarity NPC173637
0.6207 Remote Similarity NPC317489
0.6207 Remote Similarity NPC223424
0.6207 Remote Similarity NPC476772
0.6207 Remote Similarity NPC600591
0.617 Remote Similarity NPC173582
0.617 Remote Similarity NPC265885
0.617 Remote Similarity NPC181465
0.617 Remote Similarity NPC215710
0.617 Remote Similarity NPC473438
0.617 Remote Similarity NPC253788
0.6146 Remote Similarity NPC253521
0.6146 Remote Similarity NPC470125
0.6146 Remote Similarity NPC153755
0.6146 Remote Similarity NPC113836
0.6136 Remote Similarity NPC145038
0.6136 Remote Similarity NPC56077
0.6136 Remote Similarity NPC281131
0.6136 Remote Similarity NPC253662
0.6136 Remote Similarity NPC179950
0.6136 Remote Similarity NPC88789
0.6136 Remote Similarity NPC491374
0.6111 Remote Similarity NPC175107
0.602 Remote Similarity NPC473327
0.6 Remote Similarity NPC138927
0.6 Remote Similarity NPC139571
0.5979 Remote Similarity NPC61904
0.5955 Remote Similarity NPC64305
0.5955 Remote Similarity NPC265530
0.5909 Remote Similarity NPC111929
0.5909 Remote Similarity NPC320283
0.5909 Remote Similarity NPC41121
0.59 Remote Similarity NPC471669
0.5865 Remote Similarity NPC477895
0.5843 Remote Similarity NPC77672
0.5843 Remote Similarity NPC133671
0.5843 Remote Similarity NPC135391
0.5843 Remote Similarity NPC78263
0.5843 Remote Similarity NPC250069
0.5824 Remote Similarity NPC472459
0.581 Remote Similarity NPC217520
0.5795 Remote Similarity NPC67037
0.5795 Remote Similarity NPC255615
0.5761 Remote Similarity NPC60735
0.5761 Remote Similarity NPC219904
0.5761 Remote Similarity NPC26230
0.5758 Remote Similarity NPC297503
0.5743 Remote Similarity NPC476472
0.5743 Remote Similarity NPC294815
0.5743 Remote Similarity NPC16194
0.5714 Remote Similarity NPC292019
0.5714 Remote Similarity NPC202908
0.5699 Remote Similarity NPC120099
0.5699 Remote Similarity NPC189913
0.5682 Remote Similarity NPC276222
0.5682 Remote Similarity NPC274618
0.5682 Remote Similarity NPC118284
0.5682 Remote Similarity NPC608147
0.5663 Remote Similarity NPC484156
0.5652 Remote Similarity NPC325555
0.5652 Remote Similarity NPC226304
0.5604 Remote Similarity NPC158674
0.5506 Remote Similarity NPC288084
0.5474 Remote Similarity NPC223747
0.5472 Remote Similarity NPC189564
0.5455 Remote Similarity NPC293626
0.5417 Remote Similarity NPC203050
0.5417 Remote Similarity NPC225434
0.5408 Remote Similarity NPC29958
0.5402 Remote Similarity NPC25389
0.5393 Remote Similarity NPC54802
0.5393 Remote Similarity NPC197304
0.5368 Remote Similarity NPC484158
0.5368 Remote Similarity NPC609478
0.5354 Remote Similarity NPC267680
0.5354 Remote Similarity NPC471748
0.5347 Remote Similarity NPC488074
0.5312 Remote Similarity NPC209023
0.53 Remote Similarity NPC65563
0.53 Remote Similarity NPC470949
0.53 Remote Similarity NPC605592
0.5288 Remote Similarity NPC89127
0.5263 Remote Similarity NPC235260
0.5263 Remote Similarity NPC159579
0.5263 Remote Similarity NPC155763
0.5253 Remote Similarity NPC476773
0.5243 Remote Similarity NPC122467
0.5227 Remote Similarity NPC1913
0.5221 Remote Similarity NPC156785
0.5196 Remote Similarity NPC488073
0.5196 Remote Similarity NPC126784
0.5196 Remote Similarity NPC241423
0.5172 Remote Similarity NPC166277
0.5169 Remote Similarity NPC487499
0.513 Remote Similarity NPC241781
0.5114 Remote Similarity NPC472859
0.51 Remote Similarity NPC187379
0.51 Remote Similarity NPC139320
0.5094 Remote Similarity NPC36138
0.5094 Remote Similarity NPC470445
0.5093 Remote Similarity NPC121703
0.5053 Remote Similarity NPC52550
0.5053 Remote Similarity NPC349108
0.5051 Remote Similarity NPC254855
0.5051 Remote Similarity NPC94610
0.5051 Remote Similarity NPC95866
0.5047 Remote Similarity NPC470446
0.5043 Remote Similarity NPC480444

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC210632 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
0.6452 Remote Similarity NPD6797 Phase 2

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