Natural Product: NPC135391

Natural Product IDNPC135391
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Kaempferol 3-O-D-Galactoside
IUPAC Name 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL2297279
PubChem CID 5488283
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 JPUKWEQWGBDDQB-HBDJNLTOSA-N
Standard InCHI InChI=1S/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15+,17+,18-,21?/m1/s1
SMILES c1cc(ccc1c1c(c(=O)c2c(cc(cc2o1)O)O)OC1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   448.1 Volume:   413.147
?
Van der Waals volume.
Dense:   1.085 LogP:   1.047
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.283
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.727
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   4.0 Rigid Bonds:   24.0
TPSA:   190.28
?
Topological Polar Surface Area.
 H-Bond Acceptor:   11.0
H-Bond Donor:   7.0 Rings:   4.0
Heavy Atoms:   11.0

MedChem Properties

QED Drug-Likeness Score:   0.279 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.884 Fsp3:   0.286
MCE-18:   87.63
?
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:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.57 Fluc inhibitor:   0.244
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.809
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.625
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.271 Promiscuous compounds:   0.606

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -6.434 MDCK Permeability:   -5.05
Pgp-inhibitor:   0.0 Pgp-substrate:   0.631
PAMPA:   0.998
?
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):   0.094
20% Bioavailability (F20%):   0.689 30% Bioavailability (F30%):   0.978
50% Bioavailability (F50%):   0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.0 MRP1:   0.763
Plasma Protein Binding (PPB):   86.076% Volume Distribution (VD):   -0.097
Fu: 12.602%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.775
OATP1B3 inhibitor:   0.969 BCRP inhibitor:   0.228
BSEP inhibitor:   0.019

ADMET: Metabolism

CYP1A2-inhibitor:   0.021 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.136 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.027 CYP2D6-substrate:   0.432
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.03
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.881
?
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):  2.795 Half-life (T1/2):  2.685

ADMET: Toxicity

hERG Blockers:  0.017 hERG Blockers (10um):  0.159
Human Hepatotoxicity (H-HT):  0.578 Drug-induced Liver Injury (DILI):  0.845
AMES Toxicity:  0.914 Rat Oral Acute Toxicity:  0.12
Maximum Recommended Daily Dose:  0.306 Skin Sensitization:  0.997
Carcinogencity:  0.581 Eye Corrosion:  0.0
Eye Irritation:  0.944 Respiratory Toxicity:  0.235
Drug-induced Neurotoxicity:  0.026 Ototoxicity:  0.528
Hematotoxicity:  0.158 Drug-induced Nephrotoxicity:  0.15
Genotoxicity:  0.985 RPMI-8226 Immunitoxicity:  0.075
A549 Cytotoxicity:  0.853 Hek293 Cytotoxicity:  0.888
BCF:   0.562
?
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:   3.134
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.385
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.73
?
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
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. flower n.a. PMID[16378372]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. fruit n.a. PMID[16378372]
NPO17782 Inula britannica Species Asteraceae Eukaryota flowers n.a. n.a. PMID[16643020]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. PMID[19919095]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. PMID[20815207]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. bark n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[21319773]
NPO18296 Diospyros kaki Species Ebenaceae Eukaryota n.a. calyx n.a. PMID[21561086]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[22207282]
NPO18007 Agrimonia pilosa Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[22281186]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota flower buds and leaves Khon Kaen province, Thailand 2010 PMID[23270663]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Leaves n.a. n.a. PMID[23642481]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[23806866]
NPO18296 Diospyros kaki Species Ebenaceae Eukaryota n.a. fruit n.a. PMID[24086493]
NPO18093 Rosa chinensis Species Rosaceae Eukaryota Flowers Muyang, China n.a. PMID[24621197]
NPO28265 Morus alba Species Moraceae Eukaryota root bark University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic 2011-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. Konya, Turkey 2007-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota leaves Chungbuk, Korea n.a. PMID[25935644]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[25981820]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Flowers n.a. n.a. PMID[26462418]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. latex n.a. PMID[27294120]
NPO18007 Agrimonia pilosa Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[27588326]
NPO28265 Morus alba Species Moraceae Eukaryota Root barks n.a. n.a. PMID[3097265]
NPO18296 Diospyros kaki Species Ebenaceae Eukaryota n.a. n.a. n.a. PMID[37324556]
NPO28669 Cuscuta australis Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18007 Agrimonia pilosa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17782 Inula britannica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1613 Cuscuta chinensis Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20554 Astragalus complanatus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16145 Apocynum venetum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29331 Pyrrosia sheareri Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18093 Rosa chinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18296 Diospyros kaki Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16145 Apocynum venetum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1613 Cuscuta chinensis Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18296 Diospyros kaki Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18007 Agrimonia pilosa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29331 Pyrrosia sheareri Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20554 Astragalus complanatus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18093 Rosa chinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28669 Cuscuta australis Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17782 Inula britannica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28669 Cuscuta australis Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29331 Pyrrosia sheareri Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1613 Cuscuta chinensis Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17782 Inula britannica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18296 Diospyros kaki Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18007 Agrimonia pilosa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16145 Apocynum venetum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20554 Astragalus complanatus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18093 Rosa chinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18007 Agrimonia pilosa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16145 Apocynum venetum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17782 Inula britannica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1613 Cuscuta chinensis Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18093 Rosa chinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29331 Pyrrosia sheareri Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18296 Diospyros kaki Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20554 Astragalus complanatus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17782 Inula britannica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18007 Agrimonia pilosa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16145 Apocynum venetum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18296 Diospyros kaki Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20554 Astragalus complanatus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29331 Pyrrosia sheareri Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18093 Rosa chinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1613 Cuscuta chinensis Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28669 Cuscuta australis Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20554 Astragalus complanatus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18007 Agrimonia pilosa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29331 Pyrrosia sheareri Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28669 Cuscuta australis Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17782 Inula britannica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18296 Diospyros kaki Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3478 Nelumbo nucifera Species Nelumbonaceae 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
NPT204 Individual protein Acetylcholinesterase Homo sapiens IC50 = 12.0 nM DOI[10.1007/s00044-012-0353-y]

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 NPC135391 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 NPC77672
1.0 High Similarity NPC133671
1.0 High Similarity NPC78263
1.0 High Similarity NPC250069
0.8971 High Similarity NPC145038
0.8971 High Similarity NPC56077
0.8971 High Similarity NPC281131
0.8971 High Similarity NPC253662
0.8971 High Similarity NPC179950
0.8971 High Similarity NPC88789
0.8971 High Similarity NPC491374
0.8939 High Similarity NPC288084
0.8696 High Similarity NPC64305
0.8451 Intermediate Similarity NPC472459
0.8406 Intermediate Similarity NPC111929
0.8406 Intermediate Similarity NPC320283
0.8406 Intermediate Similarity NPC41121
0.8286 Intermediate Similarity NPC19388
0.8286 Intermediate Similarity NPC240431
0.8286 Intermediate Similarity NPC55786
0.8243 Intermediate Similarity NPC203050
0.8243 Intermediate Similarity NPC225434
0.8158 Intermediate Similarity NPC139320
0.8082 Intermediate Similarity NPC60735
0.8082 Intermediate Similarity NPC26230
0.8 Intermediate Similarity NPC67037
0.8 Intermediate Similarity NPC255615
0.7973 Intermediate Similarity NPC120099
0.7945 Intermediate Similarity NPC325555
0.7945 Intermediate Similarity NPC226304
0.7917 Intermediate Similarity NPC297987
0.7808 Intermediate Similarity NPC488080
0.7808 Intermediate Similarity NPC169977
0.7763 Intermediate Similarity NPC170052
0.7763 Intermediate Similarity NPC135846
0.7671 Intermediate Similarity NPC8573
0.7534 Intermediate Similarity NPC127546
0.7534 Intermediate Similarity NPC57625
0.7534 Intermediate Similarity NPC173637
0.7534 Intermediate Similarity NPC317489
0.7534 Intermediate Similarity NPC223424
0.7534 Intermediate Similarity NPC600591
0.75 Intermediate Similarity NPC156869
0.75 Intermediate Similarity NPC609478
0.7468 Intermediate Similarity NPC29958
0.7465 Intermediate Similarity NPC54802
0.7465 Intermediate Similarity NPC197304
0.7403 Intermediate Similarity NPC116458
0.7403 Intermediate Similarity NPC246943
0.7375 Intermediate Similarity NPC470405
0.7375 Intermediate Similarity NPC471748
0.7361 Intermediate Similarity NPC34531
0.7333 Intermediate Similarity NPC24043
0.725 Intermediate Similarity NPC471079
0.716 Intermediate Similarity NPC173582
0.716 Intermediate Similarity NPC265885
0.716 Intermediate Similarity NPC181465
0.716 Intermediate Similarity NPC215710
0.716 Intermediate Similarity NPC163242
0.716 Intermediate Similarity NPC272068
0.716 Intermediate Similarity NPC473438
0.716 Intermediate Similarity NPC253788
0.7159 Intermediate Similarity NPC189564
0.7143 Intermediate Similarity NPC159579
0.7143 Intermediate Similarity NPC175107
0.7051 Intermediate Similarity NPC224530
0.7013 Intermediate Similarity NPC42773
0.7013 Intermediate Similarity NPC45522
0.7 Intermediate Similarity NPC254855
0.7 Intermediate Similarity NPC94610
0.6988 Remote Similarity NPC129264
0.6974 Remote Similarity NPC136042
0.6962 Remote Similarity NPC223747
0.6933 Remote Similarity NPC135599
0.6933 Remote Similarity NPC73855
0.6933 Remote Similarity NPC113968
0.6933 Remote Similarity NPC328940
0.6933 Remote Similarity NPC277174
0.6933 Remote Similarity NPC606877
0.6905 Remote Similarity NPC470125
0.6867 Remote Similarity NPC304741
0.6854 Remote Similarity NPC203145
0.6842 Remote Similarity NPC289667
0.6795 Remote Similarity NPC599850
0.679 Remote Similarity NPC116864
0.679 Remote Similarity NPC244776
0.6782 Remote Similarity NPC76831
0.6753 Remote Similarity NPC265530
0.6744 Remote Similarity NPC270448
0.6709 Remote Similarity NPC219904
0.6705 Remote Similarity NPC292929
0.6667 Remote Similarity NPC276222
0.6667 Remote Similarity NPC476215
0.6667 Remote Similarity NPC274618
0.6667 Remote Similarity NPC118284
0.6667 Remote Similarity NPC605592
0.6667 Remote Similarity NPC608147
0.663 Remote Similarity NPC470712
0.6629 Remote Similarity NPC602448
0.6625 Remote Similarity NPC101026
0.6625 Remote Similarity NPC488077
0.6625 Remote Similarity NPC197285
0.6625 Remote Similarity NPC601710
0.6623 Remote Similarity NPC249281
0.6623 Remote Similarity NPC143851
0.6591 Remote Similarity NPC85751
0.6591 Remote Similarity NPC19240
0.6582 Remote Similarity NPC21100
0.6575 Remote Similarity NPC78697
0.6548 Remote Similarity NPC67326
0.6543 Remote Similarity NPC605784
0.6522 Remote Similarity NPC219043
0.6522 Remote Similarity NPC292019
0.6522 Remote Similarity NPC202908
0.6512 Remote Similarity NPC64425
0.65 Remote Similarity NPC191306
0.65 Remote Similarity NPC129217
0.65 Remote Similarity NPC488071
0.6471 Remote Similarity NPC203259
0.6471 Remote Similarity NPC33054
0.6471 Remote Similarity NPC155877
0.6471 Remote Similarity NPC176740
0.6471 Remote Similarity NPC471725
0.6471 Remote Similarity NPC134532
0.6471 Remote Similarity NPC602582
0.6456 Remote Similarity NPC46420
0.6456 Remote Similarity NPC84362
0.642 Remote Similarity NPC85707
0.6375 Remote Similarity NPC216496
0.6374 Remote Similarity NPC214621
0.6374 Remote Similarity NPC34267
0.6341 Remote Similarity NPC206123
0.6322 Remote Similarity NPC61904
0.6322 Remote Similarity NPC296018
0.6322 Remote Similarity NPC153755
0.6316 Remote Similarity NPC470718
0.6296 Remote Similarity NPC168584
0.6292 Remote Similarity NPC205824
0.6269 Remote Similarity NPC103342
0.6207 Remote Similarity NPC255157
0.6207 Remote Similarity NPC259896
0.618 Remote Similarity NPC37668
0.618 Remote Similarity NPC104883
0.618 Remote Similarity NPC35119
0.618 Remote Similarity NPC488679
0.617 Remote Similarity NPC48984
0.6145 Remote Similarity NPC88023
0.6145 Remote Similarity NPC309025
0.6125 Remote Similarity NPC323593
0.6125 Remote Similarity NPC203500
0.6122 Remote Similarity NPC470713
0.6098 Remote Similarity NPC235260
0.6098 Remote Similarity NPC155763
0.6098 Remote Similarity NPC48093
0.6087 Remote Similarity NPC223426
0.6076 Remote Similarity NPC476771
0.6071 Remote Similarity NPC488072
0.6071 Remote Similarity NPC276377
0.6067 Remote Similarity NPC12013
0.6067 Remote Similarity NPC11432
0.6067 Remote Similarity NPC477613
0.6049 Remote Similarity NPC52550
0.6047 Remote Similarity NPC609888
0.6044 Remote Similarity NPC476472
0.6044 Remote Similarity NPC294815
0.6044 Remote Similarity NPC16194
0.6044 Remote Similarity NPC220173
0.6024 Remote Similarity NPC259957
0.6 Remote Similarity NPC39360
0.6 Remote Similarity NPC104677
0.6 Remote Similarity NPC95866
0.6 Remote Similarity NPC29763
0.6 Remote Similarity NPC32641
0.6 Remote Similarity NPC83283
0.6 Remote Similarity NPC256188
0.6 Remote Similarity NPC210003
0.5979 Remote Similarity NPC279473
0.5977 Remote Similarity NPC39834
0.5955 Remote Similarity NPC488073
0.593 Remote Similarity NPC251417
0.5926 Remote Similarity NPC282987
0.5909 Remote Similarity NPC150164
0.5904 Remote Similarity NPC182121
0.5889 Remote Similarity NPC297503
0.5882 Remote Similarity NPC192539
0.5882 Remote Similarity NPC66087
0.587 Remote Similarity NPC471669
0.5862 Remote Similarity NPC480466
0.5854 Remote Similarity NPC305811
0.5854 Remote Similarity NPC84265
0.5851 Remote Similarity NPC81042
0.5824 Remote Similarity NPC473327
0.5806 Remote Similarity NPC221342
0.5806 Remote Similarity NPC476470
0.5802 Remote Similarity NPC112755
0.5802 Remote Similarity NPC170675
0.5802 Remote Similarity NPC254306
0.5778 Remote Similarity NPC253521
0.5778 Remote Similarity NPC154741

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC135391 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
0.6471 Remote Similarity NPD6797 Phase 2
0.5104 Remote Similarity NPD7804 Clinical (unspecified phase)

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