Structure

Physi-Chem Properties

Molecular Weight:  311.12
Volume:  307.441
LogP:  1.902
LogD:  2.343
LogS:  -2.283
# Rotatable Bonds:  1
TPSA:  59.95
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.847
Synthetic Accessibility Score:  3.318
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.178
MDCK Permeability:  1.5315630662371404e-05
Pgp-inhibitor:  0.01
Pgp-substrate:  0.979
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.782
Plasma Protein Binding (PPB):  79.8596420288086%
Volume Distribution (VD):  1.684
Pgp-substrate:  7.773611545562744%

ADMET: Metabolism

CYP1A2-inhibitor:  0.904
CYP1A2-substrate:  0.446
CYP2C19-inhibitor:  0.24
CYP2C19-substrate:  0.537
CYP2C9-inhibitor:  0.014
CYP2C9-substrate:  0.477
CYP2D6-inhibitor:  0.843
CYP2D6-substrate:  0.919
CYP3A4-inhibitor:  0.405
CYP3A4-substrate:  0.65

ADMET: Excretion

Clearance (CL):  10.848
Half-life (T1/2):  0.321

ADMET: Toxicity

hERG Blockers:  0.393
Human Hepatotoxicity (H-HT):  0.178
Drug-inuced Liver Injury (DILI):  0.474
AMES Toxicity:  0.773
Rat Oral Acute Toxicity:  0.58
Maximum Recommended Daily Dose:  0.976
Skin Sensitization:  0.364
Carcinogencity:  0.269
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.898

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC312918

Natural Product ID:  NPC312918
Common Name*:   VYJUHRAQPIBWNV-GFCCVEGCSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  VYJUHRAQPIBWNV-GFCCVEGCSA-N
Standard InCHI:  InChI=1S/C18H17NO4/c1-21-14-7-11-10(5-13(14)20)4-12-16-9(2-3-19-12)6-15-18(17(11)16)23-8-22-15/h5-7,12,19-20H,2-4,8H2,1H3/t12-/m1/s1
SMILES:  COc1cc2c(cc1O)C[C@@H]1c3c2c2OCOc2cc3CCN1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1588263
PubChem CID:   11957301
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0000381] Aporphines

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. stem wood n.a. DOI[10.1021/np100247r]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. leaf n.a. DOI[10.1080/10412905.2001.9699624]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10395501]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10425140]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[11912066]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. leaf n.a. PMID[12419922]
NPO6333 Annona glabra Species Annonaceae Eukaryota Fruits n.a. n.a. PMID[15568797]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[18217715]
NPO6333 Annona glabra Species Annonaceae Eukaryota stem Taipei Botanical Garden, Taipei, Taiwan, China 2006-MAR PMID[20828184]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. leaf n.a. PMID[21188975]
NPO6333 Annona glabra Species Annonaceae Eukaryota fruits n.a. n.a. PMID[25499882]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[9584397]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[9599260]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. n.a. Database[FooDB]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. n.a. Database[FooDB]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24160 Litsea sebifera Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24160 Litsea sebifera Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24160 Litsea sebifera Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24160 Litsea sebifera Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29515 Laurus nobilis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6333 Annona glabra Species Annonaceae 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 NP ID 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 11220.2 nM PMID[485068]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 14125.4 nM PMID[485068]
NPT1197 Individual Protein Huntingtin Homo sapiens Potency = 35481.3 nM PMID[485068]
NPT1038 Individual Protein Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 50118.7 nM PMID[485068]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 22387.2 nM PMID[485068]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 14125.4 nM PMID[485068]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 10000.0 nM PMID[485068]
NPT54 Individual Protein Nonstructural protein 1 Influenza A virus Potency = 22387.2 nM PMID[485068]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 8891.4 nM PMID[485068]
NPT56 Individual Protein Beta-lactamase AmpC Escherichia coli K-12 Potency = 631.0 nM PMID[485068]
NPT57 Individual Protein Induced myeloid leukemia cell differentiation protein Mcl-1 Homo sapiens IC50 = 5612.2 nM PMID[485068]
NPT151 Individual Protein 15-hydroxyprostaglandin dehydrogenase [NAD+] Homo sapiens Potency = 25118.9 nM PMID[485068]
NPT59 Individual Protein DNA polymerase beta Homo sapiens Potency = 39810.7 nM PMID[485068]
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 22387.2 nM PMID[485068]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 89125.1 nM PMID[485068]
NPT63 Individual Protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 22387.2 nM PMID[485068]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 14581.0 nM PMID[485068]
NPT199 Individual Protein DNA polymerase kappa Homo sapiens Potency n.a. 56234.1 nM PMID[485068]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 35481.3 nM PMID[485068]
NPT71 Cell Line HEK293 Homo sapiens Potency n.a. 16360.1 nM PMID[485068]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 18356.4 nM PMID[485068]
NPT156 Individual Protein Sphingomyelin phosphodiesterase Homo sapiens Potency n.a. 39810.7 nM PMID[485068]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 19952.6 nM PMID[485068]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 10000.0 nM PMID[485068]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 23109.3 nM PMID[485068]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 18356.4 nM PMID[485068]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 7079.5 nM PMID[485068]
NPT105 Individual Protein Muscleblind-like protein 1 Homo sapiens Potency n.a. 17782.8 nM PMID[485068]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 15848.9 nM PMID[485068]
NPT2 Others Unspecified EC50 = 13204.0 nM PMID[485068]
NPT93 Individual Protein Survival motor neuron protein Homo sapiens Potency = 56.2 nM PMID[485068]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 35481.3 nM PMID[485068]
NPT864 Individual Protein Lethal(3)malignant brain tumor-like protein 1 Homo sapiens Potency = 35481.3 nM PMID[485068]
NPT2 Others Unspecified EC50 = 85585.0 nM PMID[485068]
NPT2 Others Unspecified EC50 > 120000.0 nM PMID[485068]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 18526.0 nM PMID[485068]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 14125.4 nM PMID[485068]
NPT803 Individual Protein Flap endonuclease 1 Homo sapiens Potency n.a. 10000.0 nM PMID[485068]
NPT9 Individual Protein DNA polymerase eta Homo sapiens Potency n.a. 25118.9 nM PMID[485068]
NPT2 Others Unspecified Potency n.a. 14125.4 nM PMID[485068]
NPT2 Others Unspecified Potency n.a. 11582.1 nM PMID[485068]
NPT888 Individual Protein 78 kDa glucose-regulated protein Homo sapiens Potency n.a. 50118.7 nM PMID[485068]
NPT2 Others Unspecified Potency n.a. 10000.0 nM PMID[485068]
NPT2 Others Unspecified AC50 n.a. 27660.0 nM PMID[485068]
NPT2 Others Unspecified AC50 n.a. 84180.0 nM PMID[485068]
NPT821 Individual Protein Werner syndrome ATP-dependent helicase Homo sapiens Potency n.a. 19952.6 nM PMID[485068]
NPT755 Individual Protein Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Homo sapiens Potency n.a. 35481.3 nM PMID[485068]
NPT2 Others Unspecified Potency n.a. 20596.2 nM PMID[485068]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 23109.3 nM PMID[485068]
NPT2 Others Unspecified Potency n.a. 28183.8 nM PMID[485068]
NPT2 Others Unspecified Potency n.a. 12589.3 nM PMID[485068]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC312918 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC155442
1.0 High Similarity NPC476574
1.0 High Similarity NPC477561
0.9879 High Similarity NPC135772
0.9702 High Similarity NPC476576
0.9702 High Similarity NPC186546
0.9634 High Similarity NPC477558
0.9634 High Similarity NPC128560
0.9634 High Similarity NPC199465
0.9634 High Similarity NPC229166
0.9571 High Similarity NPC6152
0.9571 High Similarity NPC477562
0.9571 High Similarity NPC69712
0.9571 High Similarity NPC26240
0.9527 High Similarity NPC57036
0.9518 High Similarity NPC320223
0.9518 High Similarity NPC114364
0.9455 High Similarity NPC477020
0.9455 High Similarity NPC192135
0.9455 High Similarity NPC66341
0.9451 High Similarity NPC152212
0.9349 High Similarity NPC116284
0.9268 High Similarity NPC81247
0.9268 High Similarity NPC476573
0.9268 High Similarity NPC304659
0.9268 High Similarity NPC35627
0.9268 High Similarity NPC86144
0.9235 High Similarity NPC476575
0.9231 High Similarity NPC470879
0.9231 High Similarity NPC258695
0.9231 High Similarity NPC474507
0.9212 High Similarity NPC298979
0.9207 High Similarity NPC16805
0.9207 High Similarity NPC78222
0.9207 High Similarity NPC302527
0.9207 High Similarity NPC136508
0.9207 High Similarity NPC96603
0.9207 High Similarity NPC212794
0.9207 High Similarity NPC477563
0.9207 High Similarity NPC306843
0.9207 High Similarity NPC167546
0.9207 High Similarity NPC13504
0.9207 High Similarity NPC196447
0.9207 High Similarity NPC253043
0.9176 High Similarity NPC474506
0.9176 High Similarity NPC32413
0.9172 High Similarity NPC23219
0.9152 High Similarity NPC24264
0.9152 High Similarity NPC476432
0.9146 High Similarity NPC189470
0.9146 High Similarity NPC324144
0.9118 High Similarity NPC267408
0.9112 High Similarity NPC148709
0.9112 High Similarity NPC112575
0.9112 High Similarity NPC173416
0.9112 High Similarity NPC476577
0.9096 High Similarity NPC158376
0.9096 High Similarity NPC306555
0.9096 High Similarity NPC145832
0.9096 High Similarity NPC117188
0.9096 High Similarity NPC205421
0.9096 High Similarity NPC247389
0.9096 High Similarity NPC210918
0.9096 High Similarity NPC474931
0.9096 High Similarity NPC81218
0.9096 High Similarity NPC12053
0.9091 High Similarity NPC225774
0.9086 High Similarity NPC117717
0.908 High Similarity NPC82763
0.9036 High Similarity NPC219341
0.9029 High Similarity NPC475754
0.9012 High Similarity NPC275132
0.9012 High Similarity NPC248642
0.9006 High Similarity NPC126284
0.896 High Similarity NPC156576
0.8935 High Similarity NPC19520
0.8935 High Similarity NPC239775
0.8935 High Similarity NPC149090
0.8916 High Similarity NPC1229
0.8909 High Similarity NPC266753
0.8909 High Similarity NPC306902
0.8909 High Similarity NPC27410
0.8909 High Similarity NPC160298
0.8909 High Similarity NPC232924
0.8909 High Similarity NPC166014
0.8909 High Similarity NPC477559
0.8869 High Similarity NPC204947
0.8841 High Similarity NPC203784
0.8841 High Similarity NPC170503
0.8841 High Similarity NPC126519
0.878 High Similarity NPC325871
0.878 High Similarity NPC99659
0.8765 High Similarity NPC168753
0.8765 High Similarity NPC118274
0.875 High Similarity NPC214116
0.875 High Similarity NPC276944
0.875 High Similarity NPC232514
0.875 High Similarity NPC238530
0.8735 High Similarity NPC111485
0.8728 High Similarity NPC294790
0.8728 High Similarity NPC118633
0.8728 High Similarity NPC148693
0.8675 High Similarity NPC476572
0.8631 High Similarity NPC60186
0.8613 High Similarity NPC329969
0.8606 High Similarity NPC477564
0.8606 High Similarity NPC2295
0.8598 High Similarity NPC277669
0.8598 High Similarity NPC76213
0.8596 High Similarity NPC241055
0.8529 High Similarity NPC168409
0.8511 High Similarity NPC46990
0.8503 High Similarity NPC186063
0.8485 Intermediate Similarity NPC81733
0.8485 Intermediate Similarity NPC326316
0.8476 Intermediate Similarity NPC207824
0.8476 Intermediate Similarity NPC60538
0.8448 Intermediate Similarity NPC2314
0.8389 Intermediate Similarity NPC237579
0.8389 Intermediate Similarity NPC474904
0.8372 Intermediate Similarity NPC56887
0.8372 Intermediate Similarity NPC223077
0.8372 Intermediate Similarity NPC193853
0.8333 Intermediate Similarity NPC54379
0.8333 Intermediate Similarity NPC172765
0.8333 Intermediate Similarity NPC204828
0.8333 Intermediate Similarity NPC138487
0.8333 Intermediate Similarity NPC110416
0.8333 Intermediate Similarity NPC244112
0.8333 Intermediate Similarity NPC2413
0.8333 Intermediate Similarity NPC127674
0.8333 Intermediate Similarity NPC276588
0.8333 Intermediate Similarity NPC249797
0.8333 Intermediate Similarity NPC295691
0.8333 Intermediate Similarity NPC184026
0.8333 Intermediate Similarity NPC193949
0.8333 Intermediate Similarity NPC207757
0.8333 Intermediate Similarity NPC278799
0.8333 Intermediate Similarity NPC5238
0.8333 Intermediate Similarity NPC216459
0.8333 Intermediate Similarity NPC469817
0.8333 Intermediate Similarity NPC109925
0.8333 Intermediate Similarity NPC39701
0.8333 Intermediate Similarity NPC41178
0.8333 Intermediate Similarity NPC189266
0.8324 Intermediate Similarity NPC150879
0.8324 Intermediate Similarity NPC210140
0.8324 Intermediate Similarity NPC190332
0.8324 Intermediate Similarity NPC181653
0.8314 Intermediate Similarity NPC284183
0.8314 Intermediate Similarity NPC24465
0.8314 Intermediate Similarity NPC209377
0.8314 Intermediate Similarity NPC4138
0.8314 Intermediate Similarity NPC121275
0.8313 Intermediate Similarity NPC220858
0.8313 Intermediate Similarity NPC88249
0.8313 Intermediate Similarity NPC151895
0.8313 Intermediate Similarity NPC192768
0.8313 Intermediate Similarity NPC97221
0.8303 Intermediate Similarity NPC475959
0.8303 Intermediate Similarity NPC135538
0.8303 Intermediate Similarity NPC147390
0.8303 Intermediate Similarity NPC476571
0.8303 Intermediate Similarity NPC246587
0.8303 Intermediate Similarity NPC428
0.8303 Intermediate Similarity NPC24233
0.8295 Intermediate Similarity NPC187678
0.8287 Intermediate Similarity NPC312531
0.8284 Intermediate Similarity NPC146288
0.8282 Intermediate Similarity NPC294249
0.8268 Intermediate Similarity NPC233718
0.8266 Intermediate Similarity NPC124657
0.8266 Intermediate Similarity NPC13916
0.8266 Intermediate Similarity NPC264850
0.8266 Intermediate Similarity NPC195392
0.8258 Intermediate Similarity NPC32154
0.8253 Intermediate Similarity NPC103379
0.8253 Intermediate Similarity NPC477565
0.8251 Intermediate Similarity NPC478093
0.8251 Intermediate Similarity NPC24260
0.8246 Intermediate Similarity NPC205167
0.8246 Intermediate Similarity NPC249274
0.8242 Intermediate Similarity NPC191376
0.8242 Intermediate Similarity NPC321505
0.8242 Intermediate Similarity NPC179825
0.8235 Intermediate Similarity NPC79328
0.8232 Intermediate Similarity NPC320088
0.8229 Intermediate Similarity NPC311991
0.8218 Intermediate Similarity NPC100566
0.8214 Intermediate Similarity NPC233029
0.8214 Intermediate Similarity NPC210148
0.8214 Intermediate Similarity NPC26601
0.8208 Intermediate Similarity NPC134858
0.8207 Intermediate Similarity NPC478091
0.8207 Intermediate Similarity NPC473589
0.8207 Intermediate Similarity NPC478092
0.8207 Intermediate Similarity NPC30182
0.8201 Intermediate Similarity NPC244606
0.8201 Intermediate Similarity NPC156728
0.8187 Intermediate Similarity NPC477080

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC312918 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.8182 Intermediate Similarity NPD2420 Approved
0.8182 Intermediate Similarity NPD2421 Approved
0.8176 Intermediate Similarity NPD2977 Approved
0.8176 Intermediate Similarity NPD2978 Approved
0.8171 Intermediate Similarity NPD2489 Approved
0.8171 Intermediate Similarity NPD27 Approved
0.8161 Intermediate Similarity NPD3051 Approved
0.8121 Intermediate Similarity NPD3845 Phase 1
0.8121 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.8114 Intermediate Similarity NPD2969 Approved
0.8114 Intermediate Similarity NPD2970 Approved
0.8033 Intermediate Similarity NPD7906 Approved
0.7917 Intermediate Similarity NPD4584 Approved
0.7912 Intermediate Similarity NPD7313 Approved
0.7912 Intermediate Similarity NPD4578 Approved
0.7912 Intermediate Similarity NPD4577 Approved
0.7912 Intermediate Similarity NPD7310 Approved
0.7912 Intermediate Similarity NPD7312 Approved
0.7912 Intermediate Similarity NPD7311 Approved
0.7907 Intermediate Similarity NPD7298 Approved
0.788 Intermediate Similarity NPD4663 Approved
0.7879 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7869 Intermediate Similarity NPD7309 Approved
0.7869 Intermediate Similarity NPD8054 Approved
0.7869 Intermediate Similarity NPD8053 Approved
0.7857 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7817 Intermediate Similarity NPD7827 Phase 1
0.7771 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD2898 Approved
0.7765 Intermediate Similarity NPD4481 Phase 3
0.7719 Intermediate Similarity NPD6031 Approved
0.7719 Intermediate Similarity NPD6030 Approved
0.7719 Intermediate Similarity NPD4727 Phase 1
0.766 Intermediate Similarity NPD2488 Approved
0.766 Intermediate Similarity NPD2490 Approved
0.7654 Intermediate Similarity NPD4010 Discontinued
0.7651 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD5241 Discontinued
0.7528 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7528 Intermediate Similarity NPD7833 Phase 2
0.7528 Intermediate Similarity NPD7831 Phase 2
0.7515 Intermediate Similarity NPD3060 Approved
0.75 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD2494 Approved
0.7487 Intermediate Similarity NPD3452 Approved
0.7487 Intermediate Similarity NPD3450 Approved
0.7487 Intermediate Similarity NPD2493 Approved
0.7486 Intermediate Similarity NPD8252 Approved
0.7486 Intermediate Similarity NPD8251 Approved
0.7486 Intermediate Similarity NPD8099 Discontinued
0.7474 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD6071 Discontinued
0.7459 Intermediate Similarity NPD6297 Approved
0.7447 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7446 Intermediate Similarity NPD8156 Discontinued
0.7444 Intermediate Similarity NPD4666 Phase 3
0.7433 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD2560 Approved
0.7416 Intermediate Similarity NPD2563 Approved
0.7414 Intermediate Similarity NPD5976 Discontinued
0.7406 Intermediate Similarity NPD6723 Discontinued
0.7394 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD5709 Phase 3
0.7384 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD6788 Approved
0.7374 Intermediate Similarity NPD4582 Approved
0.7374 Intermediate Similarity NPD4040 Phase 1
0.7374 Intermediate Similarity NPD4583 Approved
0.7356 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD6042 Phase 2
0.7351 Intermediate Similarity NPD42 Phase 2
0.7345 Intermediate Similarity NPD4772 Phase 2
0.7345 Intermediate Similarity NPD4773 Phase 2
0.734 Intermediate Similarity NPD2971 Approved
0.734 Intermediate Similarity NPD2968 Approved
0.733 Intermediate Similarity NPD4017 Approved
0.7323 Intermediate Similarity NPD4004 Approved
0.7323 Intermediate Similarity NPD4002 Approved
0.7308 Intermediate Similarity NPD6107 Approved
0.7302 Intermediate Similarity NPD6851 Approved
0.7302 Intermediate Similarity NPD6853 Approved
0.7299 Intermediate Similarity NPD1424 Approved
0.7299 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD2974 Approved
0.7282 Intermediate Similarity NPD2975 Approved
0.7282 Intermediate Similarity NPD2973 Approved
0.7268 Intermediate Similarity NPD4166 Phase 2
0.7264 Intermediate Similarity NPD4859 Phase 1
0.7258 Intermediate Similarity NPD4873 Discontinued
0.7245 Intermediate Similarity NPD4420 Approved
0.7238 Intermediate Similarity NPD5604 Discontinued
0.7231 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD5160 Discontinued
0.7216 Intermediate Similarity NPD3641 Approved
0.7216 Intermediate Similarity NPD3639 Approved
0.7216 Intermediate Similarity NPD3640 Phase 3
0.72 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD7047 Phase 3
0.7172 Intermediate Similarity NPD4580 Approved
0.7143 Intermediate Similarity NPD3110 Approved
0.7143 Intermediate Similarity NPD6997 Phase 2
0.7143 Intermediate Similarity NPD4055 Discovery
0.7143 Intermediate Similarity NPD7598 Phase 2
0.7143 Intermediate Similarity NPD3109 Approved
0.7134 Intermediate Similarity NPD3053 Approved
0.7134 Intermediate Similarity NPD3055 Approved
0.713 Intermediate Similarity NPD8153 Approved
0.713 Intermediate Similarity NPD8152 Approved
0.7128 Intermediate Similarity NPD7479 Phase 2
0.711 Intermediate Similarity NPD4162 Approved
0.71 Intermediate Similarity NPD5005 Approved
0.71 Intermediate Similarity NPD5006 Approved
0.7076 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD4585 Approved
0.7068 Intermediate Similarity NPD7281 Phase 3
0.7068 Intermediate Similarity NPD7280 Phase 3
0.7066 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD817 Approved
0.7059 Intermediate Similarity NPD823 Approved
0.7052 Intermediate Similarity NPD4257 Approved
0.7052 Intermediate Similarity NPD4256 Phase 2
0.7039 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD2677 Approved
0.7024 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7017 Intermediate Similarity NPD3383 Approved
0.7017 Intermediate Similarity NPD3382 Approved
0.7017 Intermediate Similarity NPD3384 Approved
0.7015 Intermediate Similarity NPD2491 Approved
0.7015 Intermediate Similarity NPD3448 Approved
0.7015 Intermediate Similarity NPD3057 Approved
0.701 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD3645 Discontinued
0.7005 Intermediate Similarity NPD7922 Phase 1
0.7 Intermediate Similarity NPD8318 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6612 Phase 2
0.6982 Remote Similarity NPD2674 Phase 3
0.6974 Remote Similarity NPD3408 Clinical (unspecified phase)
0.6971 Remote Similarity NPD5754 Discontinued
0.6971 Remote Similarity NPD3977 Clinical (unspecified phase)
0.697 Remote Similarity NPD5582 Discontinued
0.6968 Remote Similarity NPD5602 Clinical (unspecified phase)
0.6966 Remote Similarity NPD6090 Discontinued
0.6964 Remote Similarity NPD5155 Approved
0.6964 Remote Similarity NPD5156 Approved
0.6952 Remote Similarity NPD4083 Discontinued
0.6948 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6944 Remote Similarity NPD7261 Clinical (unspecified phase)
0.6944 Remote Similarity NPD4005 Discontinued
0.6941 Remote Similarity NPD3059 Approved
0.6941 Remote Similarity NPD3062 Approved
0.6941 Remote Similarity NPD3061 Approved
0.6935 Remote Similarity NPD7802 Discontinued
0.6931 Remote Similarity NPD3533 Approved
0.6931 Remote Similarity NPD2972 Approved
0.6923 Remote Similarity NPD5718 Phase 2
0.6923 Remote Similarity NPD3349 Phase 2
0.6915 Remote Similarity NPD5457 Discontinued
0.6914 Remote Similarity NPD4237 Approved
0.6914 Remote Similarity NPD4236 Phase 3
0.6914 Remote Similarity NPD5177 Phase 3
0.6914 Remote Similarity NPD6674 Discontinued
0.6905 Remote Similarity NPD2606 Approved
0.6905 Remote Similarity NPD3595 Approved
0.6905 Remote Similarity NPD2605 Approved
0.6905 Remote Similarity NPD3594 Approved
0.6897 Remote Similarity NPD4721 Approved
0.6897 Remote Similarity NPD4726 Approved
0.6897 Remote Similarity NPD4725 Approved
0.6895 Remote Similarity NPD3933 Discontinued
0.6895 Remote Similarity NPD5095 Phase 3
0.6895 Remote Similarity NPD5096 Phase 3
0.6889 Remote Similarity NPD3687 Approved
0.6889 Remote Similarity NPD3686 Approved
0.6888 Remote Similarity NPD7235 Clinical (unspecified phase)
0.6882 Remote Similarity NPD1132 Approved
0.6882 Remote Similarity NPD1136 Approved
0.6882 Remote Similarity NPD1130 Approved
0.6879 Remote Similarity NPD1753 Discontinued
0.6879 Remote Similarity NPD2155 Approved
0.6879 Remote Similarity NPD4108 Discontinued
0.6879 Remote Similarity NPD2154 Approved
0.6879 Remote Similarity NPD2156 Approved
0.6875 Remote Similarity NPD7039 Approved
0.6875 Remote Similarity NPD7038 Approved
0.6872 Remote Similarity NPD3857 Clinical (unspecified phase)
0.6868 Remote Similarity NPD6072 Discontinued
0.6867 Remote Similarity NPD5310 Approved
0.6867 Remote Similarity NPD5311 Approved
0.686 Remote Similarity NPD5314 Approved
0.6857 Remote Similarity NPD7045 Clinical (unspecified phase)
0.6854 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6845 Remote Similarity NPD3636 Approved
0.6845 Remote Similarity NPD3637 Approved
0.6845 Remote Similarity NPD3635 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

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