Structure

Physi-Chem Properties

Molecular Weight:  279.13
Volume:  289.86
LogP:  3.589
LogD:  2.935
LogS:  -2.789
# Rotatable Bonds:  0
TPSA:  21.7
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.739
Synthetic Accessibility Score:  3.024
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.563
MDCK Permeability:  2.9910186640336178e-05
Pgp-inhibitor:  0.444
Pgp-substrate:  0.422
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.988
Plasma Protein Binding (PPB):  92.79058074951172%
Volume Distribution (VD):  2.863
Pgp-substrate:  3.597278118133545%

ADMET: Metabolism

CYP1A2-inhibitor:  0.919
CYP1A2-substrate:  0.662
CYP2C19-inhibitor:  0.5
CYP2C19-substrate:  0.922
CYP2C9-inhibitor:  0.029
CYP2C9-substrate:  0.595
CYP2D6-inhibitor:  0.968
CYP2D6-substrate:  0.93
CYP3A4-inhibitor:  0.697
CYP3A4-substrate:  0.881

ADMET: Excretion

Clearance (CL):  15.917
Half-life (T1/2):  0.154

ADMET: Toxicity

hERG Blockers:  0.675
Human Hepatotoxicity (H-HT):  0.189
Drug-inuced Liver Injury (DILI):  0.14
AMES Toxicity:  0.868
Rat Oral Acute Toxicity:  0.639
Maximum Recommended Daily Dose:  0.914
Skin Sensitization:  0.164
Carcinogencity:  0.768
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.79

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

  Natural Product: NPC306902

Natural Product ID:  NPC306902
Common Name*:   Roemerine
IUPAC Name:   n.a.
Synonyms:   GNF-Pf-4466
Standard InCHIKey:  JCTYWRARKVGOBK-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C18H17NO2/c1-19-7-6-12-9-15-18(21-10-20-15)17-13-5-3-2-4-11(13)8-14(19)16(12)17/h2-5,9,14H,6-8,10H2,1H3
SMILES:  CN1CCc2cc3c(c4-c5ccccc5CC1c24)OCO3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL36654
PubChem CID:   235224
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
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[1659613]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota stem bark n.a. n.a. PMID[17918910]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. stem n.a. PMID[18175990]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota Stems; Barks n.a. n.a. PMID[19086868]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. PMID[19919095]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
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]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. bark n.a. PMID[23823874]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Flowers n.a. n.a. PMID[26462418]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[28485933]
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]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11791 Magnolia obovata Species Magnoliaceae 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]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11791 Magnolia obovata Species Magnoliaceae 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]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4368 Magnolia officinalis Species Magnoliaceae 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 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
NPT4163 Individual Protein Protein tyrosine phosphatase receptor type C-associated protein Homo sapiens IC50 = 107000.0 nM PMID[551707]
NPT1229 Cell Line Huh-7 Homo sapiens CC50 = 22310.0 nM PMID[551708]
NPT537 Individual Protein Ras-related protein Rab-9A Homo sapiens Potency = 6309.6 nM PMID[551709]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 251.2 nM PMID[551709]
NPT60 Individual Protein Lysosomal alpha-glucosidase Homo sapiens Potency = 39810.7 nM PMID[551709]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 7079.5 nM PMID[551709]
NPT59 Individual Protein DNA polymerase beta Homo sapiens Potency = 15848.9 nM PMID[551709]
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 44668.4 nM PMID[551709]
NPT538 Individual Protein Niemann-Pick C1 protein Homo sapiens Potency n.a. 62841.7 nM PMID[551709]
NPT537 Individual Protein Ras-related protein Rab-9A Homo sapiens Potency n.a. 39650.4 nM PMID[551709]
NPT63 Individual Protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 79432.8 nM PMID[551709]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 11220.2 nM PMID[551709]
NPT1273 Individual Protein ATP-dependent molecular chaperone HSP82 Candida albicans (strain WO-1) (Yeast) EC50 > 150000.0 nM PMID[551709]
NPT4674 Individual Protein Apoptotic protease-activating factor 1 Homo sapiens IC50 > 100000.0 nM PMID[551709]
NPT2867 Individual Protein Protein RecA Mycobacterium tuberculosis EC50 = 79.7 nM PMID[551709]
NPT2866 Individual Protein Replicative DNA helicase Mycobacterium tuberculosis AC50 > 380000.0 nM PMID[551709]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 3548.1 nM PMID[551709]
NPT4674 Individual Protein Apoptotic protease-activating factor 1 Homo sapiens IC50 = 10200.0 nM PMID[551709]
NPT537 Individual Protein Ras-related protein Rab-9A Homo sapiens Potency n.a. 51912.0 nM PMID[551709]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 23109.3 nM PMID[551709]
NPT537 Individual Protein Ras-related protein Rab-9A Homo sapiens Potency n.a. 62841.7 nM PMID[551709]
NPT100 Individual Protein Glutaminase kidney isoform, mitochondrial Homo sapiens Potency n.a. 12589.3 nM PMID[551709]
NPT1858 Individual Protein Dopamine D2 receptor Rattus norvegicus Ki = 83.18 nM PMID[551711]
NPT1857 Individual Protein Dopamine D1 receptor Rattus norvegicus Ki = 324.34 nM PMID[551711]
NPT1858 Individual Protein Dopamine D2 receptor Rattus norvegicus Ki = 84.0 nM PMID[551711]
NPT1857 Individual Protein Dopamine D1 receptor Rattus norvegicus Ki = 377.0 nM PMID[551711]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 31622.8 nM PMID[551709]
NPT535 Individual Protein Parathyroid hormone receptor Homo sapiens Potency n.a. 2818.4 nM PMID[551709]
NPT1226 Individual Protein Caspase-7 Homo sapiens AC50 = 1510.0 nM PMID[551709]
NPT105 Individual Protein Muscleblind-like protein 1 Homo sapiens Potency n.a. 7079.5 nM PMID[551709]
NPT538 Individual Protein Niemann-Pick C1 protein Homo sapiens Potency n.a. 51912.0 nM PMID[551709]
NPT2265 Individual Protein Caspase-9 Homo sapiens AC50 > 70000.0 nM PMID[551709]
NPT5855 Individual Protein E3 ubiquitin-protein ligase UHRF1 Homo sapiens IC50 > 43799.0 nM PMID[551709]
NPT2 Others Unspecified IFI = 6.173 % PMID[551708]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum EC50 = 111.5 nM PMID[551708]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum EC50 = 93.1 nM PMID[551708]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 39810.7 nM PMID[551709]
NPT2 Others Unspecified IC50 = 1660.0 nM PMID[551709]
NPT795 Individual Protein Zinc finger protein mex-5 Caenorhabditis elegans EC50 = 21456.0 nM PMID[551709]
NPT2 Others Unspecified EC50 > 38000.0 nM PMID[551709]
NPT2 Others Unspecified EC50 > 110000.0 nM PMID[551709]
NPT2 Others Unspecified CC50 > 40000.0 nM PMID[551709]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 35481.3 nM PMID[551709]
NPT2 Others Unspecified IC50 = 2350.0 nM PMID[551709]
NPT797 Individual Protein Cytoplasmic zinc-finger protein Caenorhabditis elegans EC50 = 16837.0 nM PMID[551709]
NPT2 Others Unspecified Potency n.a. 14581.0 nM PMID[551709]
NPT21702 PROTEIN-PROTEIN INTERACTION Importin subunit beta-1/Snurportin-1 Homo sapiens Potency n.a. 125892.5 nM PMID[551709]
NPT803 Individual Protein Flap endonuclease 1 Homo sapiens Potency n.a. 50118.7 nM PMID[551709]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 15848.9 nM PMID[551709]
NPT84 Individual Protein Dual specificity tyrosine-phosphorylation-regulated kinase 1A Rattus norvegicus AC50 = 2539.0 nM PMID[551709]
NPT2 Others Unspecified EC50 > 150000.0 nM PMID[551709]
NPT2 Others Unspecified IC50 = 2730.0 nM PMID[551709]
NPT2 Others Unspecified Potency n.a. 35481.3 nM PMID[551709]
NPT2 Others Unspecified Potency n.a. 35481.3 nM PMID[551710]
NPT2 Others Unspecified Potency n.a. 562.3 nM PMID[551709]
NPT755 Individual Protein Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Homo sapiens Potency n.a. 39810.7 nM PMID[551709]
NPT2 Others Unspecified Ratio Ki = 4.4 n.a. PMID[551711]
NPT2 Others Unspecified Potency n.a. 1995.3 nM PMID[551709]
NPT2 Others Unspecified IC50 = 4695.0 nM PMID[551709]
NPT867 Individual Protein Caspase-6 Homo sapiens AC50 = 3680.0 nM PMID[551709]

☑ 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 NPC306902 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 NPC477559
1.0 High Similarity NPC160298
1.0 High Similarity NPC232924
1.0 High Similarity NPC266753
0.9803 High Similarity NPC225774
0.9739 High Similarity NPC219341
0.9739 High Similarity NPC24264
0.9739 High Similarity NPC476432
0.9675 High Similarity NPC298979
0.9675 High Similarity NPC247389
0.9673 High Similarity NPC16805
0.9673 High Similarity NPC167546
0.9673 High Similarity NPC302527
0.9613 High Similarity NPC241055
0.961 High Similarity NPC304659
0.961 High Similarity NPC86144
0.9548 High Similarity NPC210918
0.9545 High Similarity NPC168409
0.953 High Similarity NPC326316
0.953 High Similarity NPC81733
0.9481 High Similarity NPC189470
0.9367 High Similarity NPC19520
0.9367 High Similarity NPC149090
0.9304 High Similarity NPC6152
0.9255 High Similarity NPC320223
0.9255 High Similarity NPC114364
0.925 High Similarity NPC199465
0.925 High Similarity NPC229166
0.925 High Similarity NPC128560
0.9221 High Similarity NPC476572
0.9216 High Similarity NPC216459
0.9216 High Similarity NPC99659
0.9216 High Similarity NPC325871
0.9216 High Similarity NPC41178
0.9216 High Similarity NPC138487
0.92 High Similarity NPC475959
0.9198 High Similarity NPC126284
0.9182 High Similarity NPC152212
0.9156 High Similarity NPC170503
0.9156 High Similarity NPC146288
0.9156 High Similarity NPC126519
0.9156 High Similarity NPC203784
0.9103 High Similarity NPC27410
0.9103 High Similarity NPC166014
0.9091 High Similarity NPC76079
0.9085 High Similarity NPC248642
0.908 High Similarity NPC267408
0.9074 High Similarity NPC112575
0.9038 High Similarity NPC477080
0.9032 High Similarity NPC31311
0.9032 High Similarity NPC234392
0.903 High Similarity NPC156576
0.9024 High Similarity NPC474506
0.9024 High Similarity NPC32413
0.9018 High Similarity NPC23219
0.9013 High Similarity NPC219162
0.9012 High Similarity NPC477558
0.897 High Similarity NPC116284
0.8963 High Similarity NPC258695
0.8963 High Similarity NPC470879
0.8961 High Similarity NPC210148
0.8961 High Similarity NPC233029
0.8916 High Similarity NPC135772
0.8909 High Similarity NPC155442
0.8909 High Similarity NPC179704
0.8909 High Similarity NPC476574
0.8909 High Similarity NPC312918
0.8909 High Similarity NPC477561
0.8902 High Similarity NPC294790
0.8902 High Similarity NPC118633
0.8902 High Similarity NPC148693
0.8882 High Similarity NPC90844
0.8882 High Similarity NPC95075
0.8882 High Similarity NPC253883
0.8874 High Similarity NPC145304
0.8869 High Similarity NPC237579
0.8868 High Similarity NPC324144
0.8859 High Similarity NPC470925
0.8855 High Similarity NPC249405
0.8846 High Similarity NPC244112
0.8846 High Similarity NPC93593
0.8841 High Similarity NPC287588
0.8824 High Similarity NPC130941
0.882 High Similarity NPC145832
0.882 High Similarity NPC306555
0.882 High Similarity NPC81218
0.882 High Similarity NPC474931
0.882 High Similarity NPC158376
0.882 High Similarity NPC117188
0.882 High Similarity NPC205421
0.882 High Similarity NPC12053
0.8812 High Similarity NPC96603
0.8812 High Similarity NPC306843
0.8812 High Similarity NPC232514
0.8812 High Similarity NPC212794
0.8812 High Similarity NPC238530
0.8812 High Similarity NPC13504
0.8812 High Similarity NPC136508
0.8812 High Similarity NPC276944
0.8812 High Similarity NPC196447
0.8812 High Similarity NPC253043
0.8812 High Similarity NPC78222
0.8812 High Similarity NPC477563
0.881 High Similarity NPC214116
0.8792 High Similarity NPC314682
0.8766 High Similarity NPC92541
0.8758 High Similarity NPC106295
0.8758 High Similarity NPC16107
0.8758 High Similarity NPC81247
0.8758 High Similarity NPC35627
0.8758 High Similarity NPC51957
0.8758 High Similarity NPC210437
0.8758 High Similarity NPC476144
0.8758 High Similarity NPC476573
0.8757 High Similarity NPC474904
0.875 High Similarity NPC1229
0.8743 High Similarity NPC476575
0.8733 High Similarity NPC328750
0.8733 High Similarity NPC188163
0.8733 High Similarity NPC474915
0.8733 High Similarity NPC213206
0.8718 High Similarity NPC470924
0.8706 High Similarity NPC82763
0.8701 High Similarity NPC7467
0.8698 High Similarity NPC57036
0.8679 High Similarity NPC111485
0.8647 High Similarity NPC476576
0.8647 High Similarity NPC186546
0.8647 High Similarity NPC312531
0.8645 High Similarity NPC211296
0.8636 High Similarity NPC144863
0.8618 High Similarity NPC136860
0.8618 High Similarity NPC128019
0.8618 High Similarity NPC476567
0.8608 High Similarity NPC78733
0.8599 High Similarity NPC148898
0.8599 High Similarity NPC26601
0.8598 High Similarity NPC168753
0.8598 High Similarity NPC118274
0.8591 High Similarity NPC7018
0.8589 High Similarity NPC204947
0.8545 High Similarity NPC239775
0.8521 High Similarity NPC275132
0.8519 High Similarity NPC233650
0.8516 High Similarity NPC476151
0.8512 High Similarity NPC220961
0.8506 High Similarity NPC185838
0.8497 Intermediate Similarity NPC302001
0.8497 Intermediate Similarity NPC117717
0.8494 Intermediate Similarity NPC2314
0.8494 Intermediate Similarity NPC66341
0.8494 Intermediate Similarity NPC192135
0.8494 Intermediate Similarity NPC285941
0.8494 Intermediate Similarity NPC477020
0.8485 Intermediate Similarity NPC26240
0.8485 Intermediate Similarity NPC69712
0.8485 Intermediate Similarity NPC477562
0.8466 Intermediate Similarity NPC134858
0.8457 Intermediate Similarity NPC24954
0.8452 Intermediate Similarity NPC477560
0.8439 Intermediate Similarity NPC475754
0.8438 Intermediate Similarity NPC180756
0.8438 Intermediate Similarity NPC186063
0.8438 Intermediate Similarity NPC323443
0.8409 Intermediate Similarity NPC193906
0.8409 Intermediate Similarity NPC23080
0.8408 Intermediate Similarity NPC103379
0.8408 Intermediate Similarity NPC477565
0.8397 Intermediate Similarity NPC179825
0.8397 Intermediate Similarity NPC191376
0.8397 Intermediate Similarity NPC321505
0.8375 Intermediate Similarity NPC189266
0.8375 Intermediate Similarity NPC469817
0.8375 Intermediate Similarity NPC2413
0.8375 Intermediate Similarity NPC204828
0.8375 Intermediate Similarity NPC295691
0.8375 Intermediate Similarity NPC184026
0.8375 Intermediate Similarity NPC276588
0.8375 Intermediate Similarity NPC207757
0.8375 Intermediate Similarity NPC278799
0.8375 Intermediate Similarity NPC193949
0.8375 Intermediate Similarity NPC127674
0.8375 Intermediate Similarity NPC249797
0.8375 Intermediate Similarity NPC5238
0.8375 Intermediate Similarity NPC110416
0.8375 Intermediate Similarity NPC39701
0.8375 Intermediate Similarity NPC172765
0.8375 Intermediate Similarity NPC54379
0.8364 Intermediate Similarity NPC150879
0.8364 Intermediate Similarity NPC210140
0.8354 Intermediate Similarity NPC223125
0.8344 Intermediate Similarity NPC24233
0.8344 Intermediate Similarity NPC60186
0.8344 Intermediate Similarity NPC135538
0.8344 Intermediate Similarity NPC147390
0.8344 Intermediate Similarity NPC246587
0.8344 Intermediate Similarity NPC476571
0.8344 Intermediate Similarity NPC428
0.8333 Intermediate Similarity NPC106786
0.8304 Intermediate Similarity NPC233718

  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 NPC306902 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
0.8758 High Similarity NPD4584 Approved
0.8733 High Similarity NPD4664 Clinical (unspecified phase)
0.8562 High Similarity NPD5084 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD2420 Approved
0.8333 Intermediate Similarity NPD2421 Approved
0.8303 Intermediate Similarity NPD3051 Approved
0.8269 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.8204 Intermediate Similarity NPD4481 Phase 3
0.8187 Intermediate Similarity NPD4017 Approved
0.8144 Intermediate Similarity NPD2969 Approved
0.8144 Intermediate Similarity NPD2970 Approved
0.8095 Intermediate Similarity NPD27 Approved
0.8095 Intermediate Similarity NPD2489 Approved
0.8072 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.8037 Intermediate Similarity NPD7298 Approved
0.8026 Intermediate Similarity NPD3109 Approved
0.8026 Intermediate Similarity NPD3110 Approved
0.7975 Intermediate Similarity NPD5241 Discontinued
0.795 Intermediate Similarity NPD3639 Approved
0.795 Intermediate Similarity NPD3640 Phase 3
0.795 Intermediate Similarity NPD3641 Approved
0.7935 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7935 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD8252 Approved
0.7895 Intermediate Similarity NPD8099 Discontinued
0.7895 Intermediate Similarity NPD8251 Approved
0.7892 Intermediate Similarity NPD6788 Approved
0.7882 Intermediate Similarity NPD2898 Approved
0.7849 Intermediate Similarity NPD8156 Discontinued
0.7844 Intermediate Similarity NPD7831 Phase 2
0.7844 Intermediate Similarity NPD7833 Phase 2
0.7844 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.784 Intermediate Similarity NPD6030 Approved
0.784 Intermediate Similarity NPD4727 Phase 1
0.784 Intermediate Similarity NPD6031 Approved
0.7829 Intermediate Similarity NPD2968 Approved
0.7829 Intermediate Similarity NPD2971 Approved
0.7829 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7799 Intermediate Similarity NPD5754 Discontinued
0.7778 Intermediate Similarity NPD5718 Phase 2
0.7758 Intermediate Similarity NPD4772 Phase 2
0.7758 Intermediate Similarity NPD4773 Phase 2
0.7753 Intermediate Similarity NPD7906 Approved
0.7727 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD4577 Approved
0.7727 Intermediate Similarity NPD4578 Approved
0.7665 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7627 Intermediate Similarity NPD7312 Approved
0.7627 Intermediate Similarity NPD7311 Approved
0.7627 Intermediate Similarity NPD7310 Approved
0.7627 Intermediate Similarity NPD7313 Approved
0.7613 Intermediate Similarity NPD4475 Approved
0.7613 Intermediate Similarity NPD4474 Approved
0.7609 Intermediate Similarity NPD4420 Approved
0.7602 Intermediate Similarity NPD7802 Discontinued
0.7598 Intermediate Similarity NPD4663 Approved
0.7593 Intermediate Similarity NPD3845 Phase 1
0.7593 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7588 Intermediate Similarity NPD7400 Phase 3
0.7584 Intermediate Similarity NPD7309 Approved
0.7584 Intermediate Similarity NPD8053 Approved
0.7584 Intermediate Similarity NPD8054 Approved
0.7569 Intermediate Similarity NPD2490 Approved
0.7569 Intermediate Similarity NPD2488 Approved
0.7558 Intermediate Similarity NPD6071 Discontinued
0.7558 Intermediate Similarity NPD4010 Discontinued
0.7558 Intermediate Similarity NPD4166 Phase 2
0.7546 Intermediate Similarity NPD3124 Discontinued
0.7532 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD2563 Approved
0.7515 Intermediate Similarity NPD2560 Approved
0.75 Intermediate Similarity NPD6107 Approved
0.7471 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD2492 Phase 1
0.7455 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD5005 Approved
0.7447 Intermediate Similarity NPD5006 Approved
0.7444 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD7598 Phase 2
0.7435 Intermediate Similarity NPD4859 Phase 1
0.743 Intermediate Similarity NPD7281 Phase 3
0.743 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.743 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.743 Intermediate Similarity NPD7280 Phase 3
0.7425 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD6895 Approved
0.7421 Intermediate Similarity NPD6896 Approved
0.7412 Intermediate Similarity NPD5977 Approved
0.7412 Intermediate Similarity NPD5978 Approved
0.7411 Intermediate Similarity NPD3763 Approved
0.7394 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7366 Intermediate Similarity NPD2975 Approved
0.7366 Intermediate Similarity NPD2974 Approved
0.7366 Intermediate Similarity NPD2973 Approved
0.7362 Intermediate Similarity NPD6748 Discontinued
0.736 Intermediate Similarity NPD6297 Approved
0.7353 Intermediate Similarity NPD2978 Approved
0.7353 Intermediate Similarity NPD2977 Approved
0.7341 Intermediate Similarity NPD6037 Discontinued
0.7326 Intermediate Similarity NPD5604 Discontinued
0.7325 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD5976 Discontinued
0.7301 Intermediate Similarity NPD5177 Phase 3
0.7289 Intermediate Similarity NPD1424 Approved
0.7268 Intermediate Similarity NPD3349 Phase 2
0.7267 Intermediate Similarity NPD4108 Discontinued
0.7261 Intermediate Similarity NPD5155 Approved
0.7261 Intermediate Similarity NPD5156 Approved
0.725 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7249 Intermediate Similarity NPD4580 Approved
0.7247 Intermediate Similarity NPD5312 Approved
0.7247 Intermediate Similarity NPD5313 Approved
0.7225 Intermediate Similarity NPD4055 Discovery
0.7216 Intermediate Similarity NPD6687 Approved
0.7216 Intermediate Similarity NPD6688 Approved
0.7212 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD3450 Approved
0.7211 Intermediate Similarity NPD2493 Approved
0.7211 Intermediate Similarity NPD2494 Approved
0.7211 Intermediate Similarity NPD3452 Approved
0.7202 Intermediate Similarity NPD1914 Approved
0.7198 Intermediate Similarity NPD6853 Approved
0.7198 Intermediate Similarity NPD6851 Approved
0.7197 Intermediate Similarity NPD2606 Approved
0.7197 Intermediate Similarity NPD2605 Approved
0.7197 Intermediate Similarity NPD3595 Approved
0.7197 Intermediate Similarity NPD3594 Approved
0.7194 Intermediate Similarity NPD3816 Phase 1
0.7194 Intermediate Similarity NPD3815 Phase 1
0.7193 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD7247 Discontinued
0.7174 Intermediate Similarity NPD7291 Discontinued
0.7161 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD1753 Discontinued
0.7158 Intermediate Similarity NPD4107 Approved
0.7152 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7110 Phase 1
0.7135 Intermediate Similarity NPD3408 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD3637 Approved
0.7134 Intermediate Similarity NPD3636 Approved
0.7134 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD3635 Approved
0.7111 Intermediate Similarity NPD3885 Approved
0.7108 Intermediate Similarity NPD5160 Discontinued
0.7105 Intermediate Similarity NPD8095 Phase 1
0.7098 Intermediate Similarity NPD4583 Approved
0.7098 Intermediate Similarity NPD4582 Approved
0.7097 Intermediate Similarity NPD1669 Approved
0.7072 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD5457 Discontinued
0.7066 Intermediate Similarity NPD7124 Phase 2
0.7062 Intermediate Similarity NPD6747 Phase 1
0.7048 Intermediate Similarity NPD6331 Phase 2
0.7048 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD4004 Approved
0.7047 Intermediate Similarity NPD4002 Approved
0.7041 Intermediate Similarity NPD6090 Discontinued
0.7039 Intermediate Similarity NPD5966 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD4482 Phase 3
0.703 Intermediate Similarity NPD7037 Approved
0.7017 Intermediate Similarity NPD3920 Phase 2
0.7012 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD2358 Clinical (unspecified phase)
0.701 Intermediate Similarity NPD4040 Phase 1
0.7 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7294 Phase 1
0.7 Intermediate Similarity NPD7427 Discontinued
0.6995 Remote Similarity NPD3057 Approved
0.6994 Remote Similarity NPD5720 Discontinued
0.6994 Remote Similarity NPD7119 Phase 2
0.6989 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6988 Remote Similarity NPD4236 Phase 3
0.6988 Remote Similarity NPD4237 Approved
0.6982 Remote Similarity NPD7020 Approved
0.6982 Remote Similarity NPD7019 Approved
0.698 Remote Similarity NPD8318 Clinical (unspecified phase)
0.697 Remote Similarity NPD4725 Approved
0.697 Remote Similarity NPD4721 Approved
0.697 Remote Similarity NPD4726 Approved
0.6962 Remote Similarity NPD7905 Discontinued
0.6957 Remote Similarity NPD2674 Phase 3
0.6949 Remote Similarity NPD5677 Discontinued
0.6947 Remote Similarity NPD5582 Discontinued
0.6935 Remote Similarity NPD7827 Phase 1
0.6931 Remote Similarity NPD7262 Phase 1
0.6928 Remote Similarity NPD4257 Approved
0.6928 Remote Similarity NPD4256 Phase 2
0.6923 Remote Similarity NPD7479 Phase 2
0.6919 Remote Similarity NPD6523 Clinical (unspecified phase)
0.6919 Remote Similarity NPD6618 Phase 2
0.6915 Remote Similarity NPD6656 Clinical (unspecified phase)
0.6915 Remote Similarity NPD7047 Phase 3
0.6914 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6911 Remote Similarity NPD5564 Approved
0.6911 Remote Similarity NPD7034 Discontinued

  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