Natural Product: NPC4899

Natural Product IDNPC4899
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Methyl (1S,4As,6S,7R,7As)-6-Hydroxy-7-Methyl-1-[3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxy-1,4A,5,6,7,7A-Hexahydrocyclopenta[C]Pyran-4-Carboxylate
IUPAC Name methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL2135791
PubChem CID 354446
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0004081] Iridoid 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 AMBQHHVBBHTQBF-PTGPOGFDSA-N
Standard InCHI InChI=1S/C17H26O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9-,10?,11+,12?,13?,14?,16-,17?/m0/s1
SMILES C[C@H]1[C@H](C[C@@H]2C(=CO[C@H]([C@H]12)OC1C(C(C(C(CO)O1)O)O)O)C(=O)OC)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   390.15 Volume:   359.548
?
Van der Waals volume.
Dense:   1.085 LogP:   -1.754
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   -1.035
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -0.46
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   5.0 Rigid Bonds:   17.0
TPSA:   155.14
?
Topological Polar Surface Area.
 H-Bond Acceptor:   10.0
H-Bond Donor:   5.0 Rings:   3.0
Heavy Atoms:   10.0

MedChem Properties

QED Drug-Likeness Score:   0.336 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   4.69 Fsp3:   0.824
MCE-18:   56.903
?
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:   0.053 Fluc inhibitor:   0.0
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.066
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.001
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.18 Promiscuous compounds:   0.021

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -6.037 MDCK Permeability:   -5.184
Pgp-inhibitor:   0.0 Pgp-substrate:   0.807
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):   0.904
20% Bioavailability (F20%):   0.784 30% Bioavailability (F30%):   0.984
50% Bioavailability (F50%):   0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.011 MRP1:   0.961
Plasma Protein Binding (PPB):   32.662% Volume Distribution (VD):   -0.584
Fu: 71.448%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.007
OATP1B3 inhibitor:   0.596 BCRP inhibitor:   0.091
BSEP inhibitor:   0.042

ADMET: Metabolism

CYP1A2-inhibitor:   0.001 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.024 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.028 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.001
CYP3A4-inhibitor:   0.028 CYP3A4-substrate:   0.0
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.271
HLM stability:   0.003
?
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):  1.649 Half-life (T1/2):  2.713

ADMET: Toxicity

hERG Blockers:  0.028 hERG Blockers (10um):  0.27
Human Hepatotoxicity (H-HT):  0.547 Drug-induced Liver Injury (DILI):  0.752
AMES Toxicity:  0.603 Rat Oral Acute Toxicity:  0.188
Maximum Recommended Daily Dose:  0.167 Skin Sensitization:  0.742
Carcinogencity:  0.332 Eye Corrosion:  0.0
Eye Irritation:  0.176 Respiratory Toxicity:  0.031
Drug-induced Neurotoxicity:  0.342 Ototoxicity:  0.966
Hematotoxicity:  0.309 Drug-induced Nephrotoxicity:  0.423
Genotoxicity:  0.071 RPMI-8226 Immunitoxicity:  0.063
A549 Cytotoxicity:  0.038 Hek293 Cytotoxicity:  0.157
BCF:   0.143
?
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:   2.023
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   3.756
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   2.833
?
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
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[ 3619437]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. DOI[10.1002/btpr.97]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1002/elan.200403102]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11738-010-0631-6]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2012.02.124]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.plaphy.2018.10.015]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. DOI[10.1016/j.tet.2012.03.006]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[10.1016/j.tet.2012.03.006]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. DOI[10.1080/17429145.2017.1293852]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. DOI[10.1186/1750-2187-3-9]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[11077184]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[12628396]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[16317898]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[17328234]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[17449162]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[18321056]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[19235686]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota Hairy roots n.a. n.a. PMID[19271765]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[19666019]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower n.a. PMID[21804227]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower bud n.a. PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota flower buds Henan province, China 2005-MAY PMID[21942812]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[22707864]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[23088673]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. leaf n.a. PMID[23265495]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[2393954]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[24279769]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[25594733]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[26285573]
NPO9090 Patrinia villosa Species Caprifoliaceae Eukaryota n.a. leaf n.a. PMID[27019553]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota Fruits n.a. n.a. PMID[29140705]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[6619887]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[6631435]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7264679]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7264682]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7320741]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[7912074]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9090 Patrinia villosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16412 Menyanthes trifoliata Species Menyanthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6067 Strychnos ignatii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16412 Menyanthes trifoliata Species Menyanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6067 Strychnos ignatii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9090 Patrinia villosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6067 Strychnos ignatii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16412 Menyanthes trifoliata Species Menyanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9090 Patrinia villosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6067 Strychnos ignatii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9090 Patrinia villosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16412 Menyanthes trifoliata Species Menyanthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6067 Strychnos ignatii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9090 Patrinia villosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16412 Menyanthes trifoliata Species Menyanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6067 Strychnos ignatii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9090 Patrinia villosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5881 Catharanthus roseus Species Apocynaceae 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
NPT10 Individual protein Geminin Homo sapiens Potency n.a. 9200.0 nM PubChem BioAssay data set

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified n.a. Potency n.a. 354.8 nM PubChem BioAssay data set

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 NPC4899 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 NPC35185
1.0 High Similarity NPC177013
0.8364 Intermediate Similarity NPC474730
0.7391 Intermediate Similarity NPC488467
0.7333 Intermediate Similarity NPC27687
0.7288 Intermediate Similarity NPC475928
0.7183 Intermediate Similarity NPC488468
0.7119 Intermediate Similarity NPC170432
0.7049 Intermediate Similarity NPC37240
0.6833 Remote Similarity NPC117596
0.6774 Remote Similarity NPC106668
0.6721 Remote Similarity NPC255677
0.6721 Remote Similarity NPC22149
0.6721 Remote Similarity NPC306344
0.6667 Remote Similarity NPC231710
0.6667 Remote Similarity NPC470573
0.6667 Remote Similarity NPC120021
0.6667 Remote Similarity NPC216826
0.6667 Remote Similarity NPC270908
0.6667 Remote Similarity NPC65665
0.6575 Remote Similarity NPC488469
0.6462 Remote Similarity NPC488472
0.6462 Remote Similarity NPC257424
0.6349 Remote Similarity NPC148270
0.6286 Remote Similarity NPC488470
0.6212 Remote Similarity NPC222062
0.619 Remote Similarity NPC307699
0.6119 Remote Similarity NPC41681
0.6 Remote Similarity NPC61201
0.597 Remote Similarity NPC254538
0.5938 Remote Similarity NPC195510
0.5938 Remote Similarity NPC298255
0.5938 Remote Similarity NPC13171
0.5915 Remote Similarity NPC488456
0.5915 Remote Similarity NPC488471
0.5915 Remote Similarity NPC488466
0.5915 Remote Similarity NPC488465
0.5915 Remote Similarity NPC488460
0.5915 Remote Similarity NPC488462
0.5857 Remote Similarity NPC197541
0.5857 Remote Similarity NPC234304
0.5857 Remote Similarity NPC118761
0.5781 Remote Similarity NPC303451
0.5781 Remote Similarity NPC72358
0.5758 Remote Similarity NPC110701
0.5753 Remote Similarity NPC488457
0.5753 Remote Similarity NPC488464
0.5753 Remote Similarity NPC488463
0.5714 Remote Similarity NPC63897
0.5672 Remote Similarity NPC193741
0.5588 Remote Similarity NPC475851
0.5588 Remote Similarity NPC475924
0.5588 Remote Similarity NPC609500
0.55 Remote Similarity NPC202391
0.55 Remote Similarity NPC296659
0.5395 Remote Similarity NPC488461
0.5395 Remote Similarity NPC488458
0.525 Remote Similarity NPC475379
0.525 Remote Similarity NPC96599
0.5224 Remote Similarity NPC287539
0.5224 Remote Similarity NPC250545
0.5224 Remote Similarity NPC3488
0.52 Remote Similarity NPC488459
0.519 Remote Similarity NPC46641
0.5143 Remote Similarity NPC6414
0.5143 Remote Similarity NPC610085
0.5135 Remote Similarity NPC284929
0.5068 Remote Similarity NPC469543

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC4899 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