Structure

Physi-Chem Properties

Molecular Weight:  304.09
Volume:  296.545
LogP:  1.971
LogD:  1.691
LogS:  -3.137
# Rotatable Bonds:  4
TPSA:  93.04
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.717
Synthetic Accessibility Score:  3.234
Fsp3:  0.312
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.934
MDCK Permeability:  1.734176476020366e-05
Pgp-inhibitor:  0.007
Pgp-substrate:  0.992
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.216
30% Bioavailability (F30%):  0.887

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.02
Plasma Protein Binding (PPB):  84.56328582763672%
Volume Distribution (VD):  0.685
Pgp-substrate:  14.269804954528809%

ADMET: Metabolism

CYP1A2-inhibitor:  0.936
CYP1A2-substrate:  0.572
CYP2C19-inhibitor:  0.101
CYP2C19-substrate:  0.098
CYP2C9-inhibitor:  0.198
CYP2C9-substrate:  0.747
CYP2D6-inhibitor:  0.241
CYP2D6-substrate:  0.583
CYP3A4-inhibitor:  0.05
CYP3A4-substrate:  0.296

ADMET: Excretion

Clearance (CL):  10.14
Half-life (T1/2):  0.304

ADMET: Toxicity

hERG Blockers:  0.043
Human Hepatotoxicity (H-HT):  0.188
Drug-inuced Liver Injury (DILI):  0.465
AMES Toxicity:  0.029
Rat Oral Acute Toxicity:  0.249
Maximum Recommended Daily Dose:  0.809
Skin Sensitization:  0.216
Carcinogencity:  0.691
Eye Corrosion:  0.003
Eye Irritation:  0.062
Respiratory Toxicity:  0.163

Download Data

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Structure MOL file  
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  Natural Product: NPC239270

Natural Product ID:  NPC239270
Common Name*:   Oxypeucedanin Hydrate
IUPAC Name:   4-[(2R)-2,3-dihydroxy-3-methylbutoxy]furo[3,2-g]chromen-7-one
Synonyms:   Oxypeucedanin Hydrate
Standard InCHIKey:  PEWFWDOPJISUOK-CYBMUJFWSA-N
Standard InCHI:  InChI=1S/C16H16O6/c1-16(2,19)13(17)8-21-15-9-3-4-14(18)22-12(9)7-11-10(15)5-6-20-11/h3-7,13,17,19H,8H2,1-2H3/t13-/m1/s1
SMILES:  O=c1ccc2c(o1)cc1c(c2OC[C@H](C(O)(C)C)O)cco1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL454060
PubChem CID:   17536
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives
        • [CHEMONTID:0000358] Furanocoumarins
          • [CHEMONTID:0002569] Linear furanocoumarins
            • [CHEMONTID:0000202] Psoralens

*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
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(99)00119-3]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. DOI[10.5012/bkcs.2003.24.11.1699]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[12510838]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[1453177]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[15646793]
NPO30686 Citrus hystrix Species Rutaceae Eukaryota n.a. exocarp n.a. PMID[20964319]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO6125 Peucedanum ostruthium Species Apiaceae Eukaryota n.a. rhizome n.a. PMID[21627108]
NPO6125 Peucedanum ostruthium Species Apiaceae Eukaryota n.a. root n.a. PMID[21627108]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[21657081]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[23872723]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[24813739]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25333853]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27444348]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota Roots n.a. n.a. PMID[31464439]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[32996318]
NPO40834 Diplolophium buchanani Species n.a. n.a. n.a. n.a. n.a. PMID[7760070]
NPO24758.2 Angelica dahurica Under-species n.a. n.a. root n.a. n.a. PMID[9157191]
NPO3509 Angelica furcijuga Species Apiaceae Eukaryota roots Miyazaki prefecture, Japan n.a. PMID[9873511]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO6125 Peucedanum ostruthium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3509 Angelica furcijuga Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16027 Niphogeton ternata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO662 Angelica officinalis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO319 Citrus limon Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3509 Angelica furcijuga Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO662 Angelica officinalis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16027 Niphogeton ternata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6125 Peucedanum ostruthium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24644 Hansenia forbesii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24768 Sphallerocarpus gracilis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6125 Peucedanum ostruthium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24644 Hansenia forbesii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2953 Ostericum grosseserratum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3509 Angelica furcijuga Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO662 Angelica officinalis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2953 Ostericum grosseserratum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16027 Niphogeton ternata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6125 Peucedanum ostruthium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24644 Hansenia forbesii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO319 Citrus limon Species Rutaceae 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
NPO319 NPC239270 Raw Essential Oil 6.4 6.4 6.4 mg/100g Database [DUKE]

☑ 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
NPT56 Individual Protein Beta-lactamase AmpC Escherichia coli K-12 Potency = 44668.4 nM PMID[523436]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 115.8 nM PMID[523436]
NPT2107 Cell Line PSN1 Homo sapiens PC50 = 89.7 uM PMID[523439]
NPT783 Cell Line MIA PaCa-2 Homo sapiens PC50 = 79.4 uM PMID[523439]
NPT461 Cell Line PANC-1 Homo sapiens PC50 = 41.2 uM PMID[523439]
NPT65 Cell Line HepG2 Homo sapiens Activity = 92.8 % PMID[523440]
NPT65 Cell Line HepG2 Homo sapiens Activity = 47.5 % PMID[523440]
NPT32 Organism Mus musculus Mus musculus Activity = 114.8 % PMID[523434]
NPT32 Organism Mus musculus Mus musculus Activity = 69.1 % PMID[523434]
NPT985 Organism Cladosporium cucumerinum Cladosporium cucumerinum Activity = 10.0 ug PMID[523435]
NPT533 Protein-Protein Interaction Runt-related transcription factor 1/Core-binding factor subunit beta Homo sapiens Potency n.a. 1412.5 nM PMID[523436]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 737.5 nM PMID[523436]
NPT740 Individual Protein Beta-secretase 1 Homo sapiens IC50 > 500000.0 nM PMID[523438]
NPT740 Individual Protein Beta-secretase 1 Homo sapiens Inhibition = 30.7 % PMID[523438]
NPT2 Others Unspecified IC50 = 229800.0 nM PMID[523441]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 420900.0 nM PMID[523441]

☑ 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 NPC239270 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 NPC95472
1.0 High Similarity NPC303210
0.9934 High Similarity NPC14822
0.9868 High Similarity NPC49009
0.9739 High Similarity NPC169
0.9608 High Similarity NPC269495
0.9477 High Similarity NPC250769
0.9477 High Similarity NPC278010
0.9477 High Similarity NPC295608
0.9342 High Similarity NPC191104
0.9321 High Similarity NPC224165
0.9286 High Similarity NPC131725
0.9276 High Similarity NPC88445
0.9272 High Similarity NPC304443
0.9272 High Similarity NPC74539
0.9264 High Similarity NPC325176
0.9255 High Similarity NPC51404
0.9231 High Similarity NPC270044
0.9216 High Similarity NPC155882
0.9202 High Similarity NPC53917
0.9146 High Similarity NPC107244
0.9103 High Similarity NPC108937
0.9103 High Similarity NPC279218
0.908 High Similarity NPC472584
0.9045 High Similarity NPC321372
0.9045 High Similarity NPC474738
0.9045 High Similarity NPC474609
0.9045 High Similarity NPC129053
0.9045 High Similarity NPC78554
0.9045 High Similarity NPC109967
0.9045 High Similarity NPC475797
0.9045 High Similarity NPC469936
0.9032 High Similarity NPC474772
0.9032 High Similarity NPC472423
0.9032 High Similarity NPC474744
0.9018 High Similarity NPC120220
0.9013 High Similarity NPC246903
0.9006 High Similarity NPC329215
0.9006 High Similarity NPC259007
0.9006 High Similarity NPC204088
0.8974 High Similarity NPC256141
0.8974 High Similarity NPC285623
0.8974 High Similarity NPC476238
0.8974 High Similarity NPC31627
0.8974 High Similarity NPC327269
0.8968 High Similarity NPC472421
0.8968 High Similarity NPC470908
0.8961 High Similarity NPC266743
0.8951 High Similarity NPC323137
0.8938 High Similarity NPC45124
0.8938 High Similarity NPC74854
0.8938 High Similarity NPC30655
0.8931 High Similarity NPC476349
0.8931 High Similarity NPC476350
0.891 High Similarity NPC471675
0.8909 High Similarity NPC233956
0.8902 High Similarity NPC281835
0.8902 High Similarity NPC144288
0.8896 High Similarity NPC202494
0.8889 High Similarity NPC208584
0.8882 High Similarity NPC313036
0.8882 High Similarity NPC166858
0.8882 High Similarity NPC51146
0.8882 High Similarity NPC219861
0.8875 High Similarity NPC304839
0.8875 High Similarity NPC220582
0.8868 High Similarity NPC260902
0.8868 High Similarity NPC296957
0.8861 High Similarity NPC477530
0.8854 High Similarity NPC263676
0.8854 High Similarity NPC473996
0.8846 High Similarity NPC180351
0.8846 High Similarity NPC321387
0.8846 High Similarity NPC327059
0.8834 High Similarity NPC67450
0.8834 High Similarity NPC155264
0.8834 High Similarity NPC193881
0.8834 High Similarity NPC210460
0.8831 High Similarity NPC190572
0.8831 High Similarity NPC474302
0.8827 High Similarity NPC472581
0.882 High Similarity NPC92589
0.882 High Similarity NPC216092
0.8805 High Similarity NPC470625
0.8805 High Similarity NPC160015
0.8805 High Similarity NPC19860
0.8805 High Similarity NPC247677
0.8797 High Similarity NPC472583
0.8797 High Similarity NPC469405
0.8797 High Similarity NPC122365
0.8797 High Similarity NPC223701
0.8797 High Similarity NPC7989
0.879 High Similarity NPC472420
0.879 High Similarity NPC290671
0.879 High Similarity NPC472580
0.879 High Similarity NPC263384
0.879 High Similarity NPC471676
0.879 High Similarity NPC472422
0.879 High Similarity NPC472636
0.879 High Similarity NPC244577
0.8782 High Similarity NPC37226
0.8782 High Similarity NPC39929
0.8782 High Similarity NPC296030
0.8782 High Similarity NPC317492
0.8782 High Similarity NPC226644
0.878 High Similarity NPC476459
0.8774 High Similarity NPC14875
0.8773 High Similarity NPC136641
0.8773 High Similarity NPC173149
0.8773 High Similarity NPC179015
0.8766 High Similarity NPC171656
0.8766 High Similarity NPC297788
0.8765 High Similarity NPC78612
0.8765 High Similarity NPC234536
0.8758 High Similarity NPC260296
0.8758 High Similarity NPC115432
0.8758 High Similarity NPC243509
0.875 High Similarity NPC470856
0.875 High Similarity NPC65504
0.8742 High Similarity NPC474542
0.8742 High Similarity NPC469934
0.8742 High Similarity NPC470681
0.8734 High Similarity NPC477957
0.8726 High Similarity NPC135303
0.8726 High Similarity NPC148423
0.8726 High Similarity NPC474735
0.872 High Similarity NPC53640
0.8718 High Similarity NPC168085
0.8712 High Similarity NPC179464
0.8712 High Similarity NPC155640
0.8712 High Similarity NPC15819
0.871 High Similarity NPC316769
0.8696 High Similarity NPC244750
0.8696 High Similarity NPC33320
0.8693 High Similarity NPC254010
0.8688 High Similarity NPC17521
0.8684 High Similarity NPC262635
0.8684 High Similarity NPC472515
0.8679 High Similarity NPC1477
0.8679 High Similarity NPC472462
0.8679 High Similarity NPC213608
0.8671 High Similarity NPC170169
0.8671 High Similarity NPC471677
0.8671 High Similarity NPC116604
0.8671 High Similarity NPC98028
0.8663 High Similarity NPC73703
0.8662 High Similarity NPC164299
0.8662 High Similarity NPC221868
0.8662 High Similarity NPC37208
0.8655 High Similarity NPC472663
0.8655 High Similarity NPC472662
0.8654 High Similarity NPC91902
0.8654 High Similarity NPC12148
0.8654 High Similarity NPC222298
0.8654 High Similarity NPC473133
0.8654 High Similarity NPC85773
0.8654 High Similarity NPC51070
0.8654 High Similarity NPC285748
0.8654 High Similarity NPC130581
0.8654 High Similarity NPC198427
0.8654 High Similarity NPC47388
0.8654 High Similarity NPC470670
0.8645 High Similarity NPC294365
0.8645 High Similarity NPC470857
0.8645 High Similarity NPC316535
0.8642 High Similarity NPC328102
0.8636 High Similarity NPC294432
0.8625 High Similarity NPC207809
0.8625 High Similarity NPC473241
0.8625 High Similarity NPC477958
0.8625 High Similarity NPC217706
0.8625 High Similarity NPC259710
0.8625 High Similarity NPC304207
0.8625 High Similarity NPC48579
0.8625 High Similarity NPC198490
0.8616 High Similarity NPC171651
0.8616 High Similarity NPC161881
0.8616 High Similarity NPC67654
0.8616 High Similarity NPC475790
0.8616 High Similarity NPC150123
0.8616 High Similarity NPC10807
0.8616 High Similarity NPC244583
0.8616 High Similarity NPC243171
0.8616 High Similarity NPC56232
0.8616 High Similarity NPC5871
0.8616 High Similarity NPC130015
0.8616 High Similarity NPC38361
0.8616 High Similarity NPC35567
0.8608 High Similarity NPC230713
0.8608 High Similarity NPC78335
0.8608 High Similarity NPC472406
0.8608 High Similarity NPC179178
0.8608 High Similarity NPC61258
0.8606 High Similarity NPC255787
0.8599 High Similarity NPC135325
0.8599 High Similarity NPC272194
0.8599 High Similarity NPC10097
0.8599 High Similarity NPC306788
0.8598 High Similarity NPC471286
0.8598 High Similarity NPC124038

  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 NPC239270 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
0.9272 High Similarity NPD920 Approved
0.9013 High Similarity NPD642 Clinical (unspecified phase)
0.8882 High Similarity NPD643 Clinical (unspecified phase)
0.8734 High Similarity NPD6801 Discontinued
0.8696 High Similarity NPD919 Approved
0.8684 High Similarity NPD1243 Approved
0.8679 High Similarity NPD7096 Clinical (unspecified phase)
0.8571 High Similarity NPD6559 Discontinued
0.8519 High Similarity NPD7075 Discontinued
0.8491 Intermediate Similarity NPD4380 Phase 2
0.8462 Intermediate Similarity NPD6799 Approved
0.8364 Intermediate Similarity NPD1247 Approved
0.8293 Intermediate Similarity NPD3749 Approved
0.8293 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8291 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD6599 Discontinued
0.8247 Intermediate Similarity NPD2796 Approved
0.8225 Intermediate Similarity NPD3818 Discontinued
0.8221 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8221 Intermediate Similarity NPD7819 Suspended
0.821 Intermediate Similarity NPD7411 Suspended
0.8171 Intermediate Similarity NPD3817 Phase 2
0.8121 Intermediate Similarity NPD3882 Suspended
0.8084 Intermediate Similarity NPD5494 Approved
0.8075 Intermediate Similarity NPD5403 Approved
0.807 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8063 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8063 Intermediate Similarity NPD5401 Approved
0.8061 Intermediate Similarity NPD5402 Approved
0.8049 Intermediate Similarity NPD1934 Approved
0.8025 Intermediate Similarity NPD1549 Phase 2
0.8 Intermediate Similarity NPD2801 Approved
0.7975 Intermediate Similarity NPD2800 Approved
0.7965 Intermediate Similarity NPD5844 Phase 1
0.7962 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7962 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7962 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.795 Intermediate Similarity NPD2532 Approved
0.795 Intermediate Similarity NPD2534 Approved
0.795 Intermediate Similarity NPD2533 Approved
0.7949 Intermediate Similarity NPD1510 Phase 2
0.7925 Intermediate Similarity NPD4628 Phase 3
0.791 Intermediate Similarity NPD8434 Phase 2
0.7904 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7904 Intermediate Similarity NPD7768 Phase 2
0.7898 Intermediate Similarity NPD1551 Phase 2
0.7895 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7862 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7844 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7834 Intermediate Similarity NPD2799 Discontinued
0.7812 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7806 Intermediate Similarity NPD1240 Approved
0.7792 Intermediate Similarity NPD2313 Discontinued
0.7792 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD6166 Phase 2
0.7791 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD1511 Approved
0.7778 Intermediate Similarity NPD6232 Discontinued
0.7759 Intermediate Similarity NPD7054 Approved
0.7759 Intermediate Similarity NPD7286 Phase 2
0.7746 Intermediate Similarity NPD7473 Discontinued
0.7736 Intermediate Similarity NPD2344 Approved
0.7733 Intermediate Similarity NPD3926 Phase 2
0.7719 Intermediate Similarity NPD6959 Discontinued
0.7714 Intermediate Similarity NPD7472 Approved
0.7714 Intermediate Similarity NPD7074 Phase 3
0.7707 Intermediate Similarity NPD1607 Approved
0.7702 Intermediate Similarity NPD3750 Approved
0.7688 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7683 Intermediate Similarity NPD1512 Approved
0.7673 Intermediate Similarity NPD2935 Discontinued
0.767 Intermediate Similarity NPD6797 Phase 2
0.767 Intermediate Similarity NPD5953 Discontinued
0.7627 Intermediate Similarity NPD7251 Discontinued
0.761 Intermediate Similarity NPD3748 Approved
0.761 Intermediate Similarity NPD7033 Discontinued
0.76 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD7808 Phase 3
0.7574 Intermediate Similarity NPD1465 Phase 2
0.7571 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD6832 Phase 2
0.7546 Intermediate Similarity NPD2309 Approved
0.7545 Intermediate Similarity NPD3226 Approved
0.7532 Intermediate Similarity NPD5124 Phase 1
0.7532 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7473 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD2424 Discontinued
0.7446 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD1652 Phase 2
0.7421 Intermediate Similarity NPD447 Suspended
0.7407 Intermediate Similarity NPD2346 Discontinued
0.7399 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD9717 Approved
0.7375 Intermediate Similarity NPD6651 Approved
0.7371 Intermediate Similarity NPD7229 Phase 3
0.7371 Intermediate Similarity NPD5711 Approved
0.7371 Intermediate Similarity NPD5710 Approved
0.7371 Intermediate Similarity NPD6808 Phase 2
0.7368 Intermediate Similarity NPD5761 Phase 2
0.7368 Intermediate Similarity NPD5760 Phase 2
0.7355 Intermediate Similarity NPD1203 Approved
0.7337 Intermediate Similarity NPD4287 Approved
0.7314 Intermediate Similarity NPD7199 Phase 2
0.7312 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD230 Phase 1
0.7312 Intermediate Similarity NPD6355 Discontinued
0.7303 Intermediate Similarity NPD3751 Discontinued
0.7288 Intermediate Similarity NPD2403 Approved
0.7284 Intermediate Similarity NPD4308 Phase 3
0.7273 Intermediate Similarity NPD3787 Discontinued
0.7267 Intermediate Similarity NPD8455 Phase 2
0.7253 Intermediate Similarity NPD8312 Approved
0.7253 Intermediate Similarity NPD8313 Approved
0.7251 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7243 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD6798 Discontinued
0.7233 Intermediate Similarity NPD3268 Approved
0.7222 Intermediate Similarity NPD1729 Discontinued
0.7216 Intermediate Similarity NPD7584 Approved
0.7209 Intermediate Similarity NPD37 Approved
0.7208 Intermediate Similarity NPD422 Phase 1
0.7202 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD1019 Discontinued
0.7195 Intermediate Similarity NPD6004 Phase 3
0.7195 Intermediate Similarity NPD6002 Phase 3
0.7195 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD6005 Phase 3
0.7195 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD4966 Approved
0.7184 Intermediate Similarity NPD4967 Phase 2
0.7184 Intermediate Similarity NPD4965 Approved
0.7169 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD5049 Phase 3
0.7143 Intermediate Similarity NPD6764 Approved
0.7143 Intermediate Similarity NPD943 Approved
0.7143 Intermediate Similarity NPD4307 Phase 2
0.7143 Intermediate Similarity NPD6765 Approved
0.7135 Intermediate Similarity NPD7458 Discontinued
0.7135 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD2797 Approved
0.7128 Intermediate Similarity NPD7583 Approved
0.7126 Intermediate Similarity NPD2354 Approved
0.7126 Intermediate Similarity NPD3887 Approved
0.7125 Intermediate Similarity NPD1296 Phase 2
0.7125 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD6280 Approved
0.711 Intermediate Similarity NPD6279 Approved
0.7108 Intermediate Similarity NPD2654 Approved
0.7102 Intermediate Similarity NPD6234 Discontinued
0.7099 Intermediate Similarity NPD1933 Approved
0.7097 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD4575 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD7585 Approved
0.7091 Intermediate Similarity NPD1471 Phase 3
0.709 Intermediate Similarity NPD4363 Phase 3
0.709 Intermediate Similarity NPD4360 Phase 2
0.7089 Intermediate Similarity NPD2798 Approved
0.7081 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD6233 Phase 2
0.7076 Intermediate Similarity NPD1653 Approved
0.7071 Intermediate Similarity NPD7783 Phase 2
0.7071 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD7435 Discontinued
0.7059 Intermediate Similarity NPD6273 Approved
0.7056 Intermediate Similarity NPD8151 Discontinued
0.7053 Intermediate Similarity NPD4361 Phase 2
0.7053 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD8150 Discontinued
0.7041 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD2296 Approved
0.7025 Intermediate Similarity NPD3266 Approved
0.7025 Intermediate Similarity NPD3267 Approved
0.7024 Intermediate Similarity NPD6190 Approved
0.7019 Intermediate Similarity NPD411 Approved
0.7019 Intermediate Similarity NPD3764 Approved
0.7 Intermediate Similarity NPD4661 Approved
0.7 Intermediate Similarity NPD4662 Approved
0.6995 Remote Similarity NPD6776 Approved
0.6995 Remote Similarity NPD6779 Approved
0.6995 Remote Similarity NPD6778 Approved
0.6995 Remote Similarity NPD6782 Approved
0.6995 Remote Similarity NPD6780 Approved
0.6995 Remote Similarity NPD6777 Approved
0.6995 Remote Similarity NPD6781 Approved
0.6989 Remote Similarity NPD6785 Approved
0.6989 Remote Similarity NPD6784 Approved
0.6981 Remote Similarity NPD5647 Approved
0.697 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6962 Remote Similarity NPD3225 Approved
0.6957 Remote Similarity NPD7685 Pre-registration
0.6954 Remote Similarity NPD5889 Approved
0.6954 Remote Similarity NPD5890 Approved
0.6948 Remote Similarity NPD9545 Approved
0.6944 Remote Similarity NPD5242 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