Structure

Physi-Chem Properties

Molecular Weight:  270.09
Volume:  276.329
LogP:  4.439
LogD:  3.624
LogS:  -4.885
# Rotatable Bonds:  3
TPSA:  52.58
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.535
Synthetic Accessibility Score:  2.674
Fsp3:  0.188
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.761
MDCK Permeability:  2.0566252715070732e-05
Pgp-inhibitor:  0.038
Pgp-substrate:  0.558
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.015
30% Bioavailability (F30%):  0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.01
Plasma Protein Binding (PPB):  83.98088836669922%
Volume Distribution (VD):  0.978
Pgp-substrate:  10.704306602478027%

ADMET: Metabolism

CYP1A2-inhibitor:  0.986
CYP1A2-substrate:  0.522
CYP2C19-inhibitor:  0.946
CYP2C19-substrate:  0.095
CYP2C9-inhibitor:  0.623
CYP2C9-substrate:  0.843
CYP2D6-inhibitor:  0.742
CYP2D6-substrate:  0.77
CYP3A4-inhibitor:  0.644
CYP3A4-substrate:  0.202

ADMET: Excretion

Clearance (CL):  13.699
Half-life (T1/2):  0.18

ADMET: Toxicity

hERG Blockers:  0.08
Human Hepatotoxicity (H-HT):  0.907
Drug-inuced Liver Injury (DILI):  0.875
AMES Toxicity:  0.069
Rat Oral Acute Toxicity:  0.115
Maximum Recommended Daily Dose:  0.238
Skin Sensitization:  0.144
Carcinogencity:  0.59
Eye Corrosion:  0.003
Eye Irritation:  0.713
Respiratory Toxicity:  0.533

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

  Natural Product: NPC88445

Natural Product ID:  NPC88445
Common Name*:   Isoimperatorin
IUPAC Name:   4-(3-methylbut-2-enoxy)furo[3,2-g]chromen-7-one
Synonyms:   Isoimperatorin
Standard InCHIKey:  IGWDEVSBEKYORK-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H14O4/c1-10(2)5-7-19-16-11-3-4-15(17)20-14(11)9-13-12(16)6-8-18-13/h3-6,8-9H,7H2,1-2H3
SMILES:  CC(=CCOc1c2ccc(=O)oc2cc2c1cco2)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL448060
PubChem CID:   68081
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
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. whole plant n.a. DOI[10.1007/BF02329610]
NPO27288 Citrus maxima 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]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. callus n.a. PMID[10552648]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[11374978]
NPO26919 Sanguisorba officinalis Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[11520216]
NPO12078 Teclea nobilis Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[12350171]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[12510838]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota leaves n.a. n.a. PMID[12568545]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[12628396]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[1453177]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. PMID[15270561]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[15646793]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15679317]
NPO27036 Xenia blumi Species Xeniidae Eukaryota n.a. Green Island, Taiwan 2002-MAY PMID[16180809]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[16309325]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota roots purchased from Kiu Shun Trading Ltd., Vancouver, Canada 2000 PMID[16643021]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. Seoul, Korea 2000-Jun PMID[16643034]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. root n.a. PMID[17238120]
NPO157 Convallaria majalis Species Asparagaceae Eukaryota n.a. rhizome n.a. PMID[17268112]
NPO6365 Pachychalina alcaloidifera Species Niphatidae Eukaryota n.a. Brazilian n.a. PMID[17346073]
NPO29994 Angelica koreana Species Apiaceae Eukaryota n.a. root n.a. PMID[17396918]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[17703773]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[17997069]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. leaf n.a. PMID[18214349]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. root n.a. PMID[18405608]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruit n.a. n.a. PMID[18505286]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. root n.a. PMID[18661821]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[19191562]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota Hairy roots n.a. n.a. PMID[19271765]
NPO23546 Clausena lansium Species Rutaceae Eukaryota leaves n.a. n.a. PMID[19327990]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruit n.a. n.a. PMID[19650637]
NPO5227 Lawsonia inermis Species Lythraceae Eukaryota leaves n.a. n.a. PMID[20634065]
NPO30526 0topterygium incisum n.a. n.a. n.a. n.a. root n.a. PMID[20707067]
NPO30526 0topterygium incisum n.a. n.a. n.a. n.a. rhizome n.a. PMID[20707067]
NPO30686 Citrus hystrix Species Rutaceae Eukaryota n.a. exocarp n.a. PMID[20964319]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. seed n.a. PMID[21049975]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21417376]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO6125 Peucedanum ostruthium Species Apiaceae Eukaryota n.a. root n.a. PMID[21627108]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21627108]
NPO6125 Peucedanum ostruthium Species Apiaceae Eukaryota n.a. rhizome n.a. PMID[21627108]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[21657081]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21800857]
NPO23546 Clausena lansium Species Rutaceae Eukaryota Stems n.a. n.a. PMID[22372931]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruits n.a. n.a. PMID[23305920]
NPO23546 Clausena lansium Species Rutaceae Eukaryota Roots n.a. n.a. PMID[24798144]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[24813739]
NPO6749 Bergenia crassifolia Species Saxifragaceae Eukaryota n.a. leaf n.a. PMID[24895781]
NPO8797 Cudrania tricuspidata Species Moraceae Eukaryota Root barks n.a. n.a. PMID[25051453]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25333853]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25538068]
NPO5227 Lawsonia inermis Species Lythraceae Eukaryota flower buds n.a. n.a. PMID[25987378]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[26285573]
NPO23546 Clausena lansium Species Rutaceae Eukaryota Leaves n.a. n.a. PMID[26523463]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27400088]
NPO8797 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. PMID[27420919]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27444348]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota Whole Plants n.a. n.a. PMID[28093914]
NPO40301 Prangos haussknechtii Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[28885836]
NPO27785 Atalantia buxifolia Species Rutaceae Eukaryota Twigs n.a. n.a. PMID[29975532]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota Roots n.a. n.a. PMID[31464439]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[32141747]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[6619887]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[6631435]
NPO157 Convallaria majalis Species Asparagaceae Eukaryota n.a. rhizome n.a. PMID[6893493]
NPO157 Convallaria majalis Species Asparagaceae Eukaryota n.a. aerial part n.a. PMID[6893493]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7264679]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7264682]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7320741]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. root n.a. PMID[7700984]
NPO3509 Angelica furcijuga Species Apiaceae Eukaryota roots Miyazaki prefecture, Japan n.a. PMID[9873511]
NPO8583 Angelica japonica Species Apiaceae Eukaryota n.a. root n.a. PMID[9987830]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25198 Octopus vulgaris Species Octopodidae Eukaryota n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25198 Octopus vulgaris Species Octopodidae Eukaryota n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO30125 0topterygium forbesii n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16027 Niphogeton ternata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27785 Atalantia buxifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO662 Angelica officinalis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5227 Lawsonia inermis Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13291 Changium smyrnioides Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26919 Sanguisorba officinalis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8874 Glehnia littoralis 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]
NPO25198 Octopus vulgaris Species Octopodidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23546 Clausena lansium 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]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8583 Angelica japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8471 Angelica taiwaniana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3509 Angelica furcijuga Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6125 Peucedanum ostruthium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6749 Bergenia crassifolia Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30526 0topterygium incisum n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2921 Angelica acutiloba 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]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO5227 Lawsonia inermis Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8797 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25198 Octopus vulgaris Species Octopodidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3509 Angelica furcijuga Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16027 Niphogeton ternata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12730 Heracleum maximum 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]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2921 Angelica acutiloba 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]
NPO27785 Atalantia buxifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8471 Angelica taiwaniana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13291 Changium smyrnioides 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]
NPO23546 Clausena lansium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26919 Sanguisorba officinalis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6749 Bergenia crassifolia Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12078 Teclea nobilis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO662 Angelica officinalis 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]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8583 Angelica japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5881 Catharanthus roseus Species Apocynaceae 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]
NPO23546 Clausena lansium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22273 Angelica pubescens 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]
NPO27785 Atalantia buxifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26919 Sanguisorba officinalis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30713 Angelica talwaniana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30125 0topterygium forbesii n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30526 0topterygium incisum n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6125 Peucedanum ostruthium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2921 Angelica acutiloba 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]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2392 Hansenia weberbaueriana Species Apiaceae 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]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3127 Aralia continentalis Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26919 Sanguisorba officinalis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13291 Changium smyrnioides 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]
NPO27288 Citrus maxima Species Rutaceae 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]
NPO2921 Angelica acutiloba 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]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9518 Gardenia jasminoides Species Rubiaceae 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]
NPO1763 Rabdosia angustifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22273 Angelica pubescens 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]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8583 Angelica japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12078 Teclea nobilis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26501 Palafoxia texana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1420 Tenebrio obscurus Species Tenebrionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6125 Peucedanum ostruthium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26387 Linum crispum Species Linaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26919 Sanguisorba officinalis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23546 Clausena lansium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12730 Heracleum maximum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16296 Macrococculus pomiferus Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26056 Atroxima liberica Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8710 Licaria brasiliensis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8797 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6365 Pachychalina alcaloidifera Species Niphatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO157 Convallaria majalis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6177 Veronicastrum japonicum Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25198 Octopus vulgaris Species Octopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24644 Hansenia forbesii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25071 Aspergillus albus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27785 Atalantia buxifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO832 Pseudocinchona pachyceras Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25444 Christisonia bicolor Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8471 Angelica taiwaniana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1068 Platytaenia lasiocarpa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO2953 Ostericum grosseserratum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3127 Aralia continentalis Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8830 Crotalaria orixensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16614 Zanthoxylum spinosum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2352 Tynanthus panurensis Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27036 Xenia blumi Species Xeniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6749 Bergenia crassifolia Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21533 Smilax bracteata Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16027 Niphogeton ternata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO662 Angelica officinalis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25123 Scutellaria sieberi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3509 Angelica furcijuga 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]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5227 Lawsonia inermis Species Lythraceae 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
NPO5954 NPC88445 Raw Fruit 0.3 0 0.6 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
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 69000.0 nM PMID[558094]
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 31622.8 nM PMID[558096]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 63095.7 nM PMID[558096]
NPT63 Individual Protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 50118.7 nM PMID[558096]
NPT160 Individual Protein TAR DNA-binding protein 43 Homo sapiens Potency n.a. 17782.8 nM PMID[558097]
NPT535 Individual Protein Parathyroid hormone receptor Homo sapiens Potency n.a. 112201.8 nM PMID[558097]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 7079.5 nM PMID[558096]
NPT1604 Individual Protein Cytochrome P450 1B1 Homo sapiens Ki = 6000.0 nM PMID[558105]
NPT2740 Cell Line Neutrophils IC50 > 10000.0 nM PMID[558107]
NPT2740 Cell Line Neutrophils IC50 = 2600.0 nM PMID[558107]
NPT81 Cell Line A549 Homo sapiens IC50 > 20.0 ug.mL-1 PMID[558107]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 20.0 ug.mL-1 PMID[558107]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 20.0 ug.mL-1 PMID[558107]
NPT2107 Cell Line PSN1 Homo sapiens PC50 = 41.7 uM PMID[558109]
NPT783 Cell Line MIA PaCa-2 Homo sapiens PC50 = 37.2 uM PMID[558109]
NPT461 Cell Line PANC-1 Homo sapiens PC50 = 41.2 uM PMID[558109]
NPT65 Cell Line HepG2 Homo sapiens Activity = 71.1 % PMID[558111]
NPT65 Cell Line HepG2 Homo sapiens Activity = 67.0 % PMID[558111]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus IC50 = 25600.0 nM PMID[558112]
NPT582 Individual Protein Monoamine oxidase B Homo sapiens IC50 > 60000.0 nM PMID[558112]
NPT261 Individual Protein Monoamine oxidase A Homo sapiens IC50 > 20000.0 nM PMID[558112]
NPT582 Individual Protein Monoamine oxidase B Homo sapiens Activity = 78.3 % PMID[558112]
NPT261 Individual Protein Monoamine oxidase A Homo sapiens Activity = 76.2 % PMID[558112]
NPT740 Individual Protein Beta-secretase 1 Homo sapiens IC50 = 244200.0 nM PMID[558095]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 39810.7 nM PMID[558096]
NPT2 Others Unspecified Potency = 4610.9 nM PMID[558096]
NPT2 Others Unspecified EC50 > 120000.0 nM PMID[558097]
NPT67 Individual Protein Cholinesterase Equus caballus IC50 = 23100.0 nM PMID[558098]
NPT2 Others Unspecified Potency n.a. 23109.3 nM PMID[558096]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 70794.6 nM PMID[558097]
NPT740 Individual Protein Beta-secretase 1 Homo sapiens IC50 = 244200.0 nM PMID[558100]
NPT2 Others Unspecified Potency n.a. 22387.2 nM PMID[558097]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 64.0 ug.mL-1 PMID[558102]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 4200.0 nM PMID[558103]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 10000.0 nM PMID[558103]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 3500.0 nM PMID[558104]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 > 50000.0 nM PMID[558104]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 9200.0 nM PMID[558104]
NPT2 Others Unspecified IC50 = 63700.0 nM PMID[558106]
NPT1007 Protein Complex GABA-A receptor; alpha-1/beta-2/gamma-2 Homo sapiens Activity > 20.0 % PMID[558110]

☑ 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 NPC88445 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
0.993 High Similarity NPC191104
0.9859 High Similarity NPC304443
0.9859 High Similarity NPC74539
0.9718 High Similarity NPC246903
0.9653 High Similarity NPC266743
0.958 High Similarity NPC208584
0.9577 High Similarity NPC166858
0.9577 High Similarity NPC51146
0.9577 High Similarity NPC313036
0.953 High Similarity NPC269495
0.9527 High Similarity NPC278010
0.9527 High Similarity NPC250769
0.9527 High Similarity NPC295608
0.9514 High Similarity NPC190572
0.9459 High Similarity NPC131725
0.9404 High Similarity NPC49009
0.9404 High Similarity NPC169
0.94 High Similarity NPC270044
0.9388 High Similarity NPC135303
0.9388 High Similarity NPC148423
0.9388 High Similarity NPC155882
0.9371 High Similarity NPC254010
0.9366 High Similarity NPC262635
0.9342 High Similarity NPC14822
0.9315 High Similarity NPC198427
0.9276 High Similarity NPC239270
0.9276 High Similarity NPC303210
0.9276 High Similarity NPC95472
0.9262 High Similarity NPC130015
0.9262 High Similarity NPC38361
0.9252 High Similarity NPC306788
0.92 High Similarity NPC41719
0.9195 High Similarity NPC472407
0.9167 High Similarity NPC470856
0.915 High Similarity NPC243509
0.9139 High Similarity NPC233776
0.9133 High Similarity NPC263676
0.9128 High Similarity NPC472406
0.9103 High Similarity NPC210460
0.9103 High Similarity NPC155264
0.9103 High Similarity NPC67450
0.9103 High Similarity NPC193881
0.9097 High Similarity NPC179464
0.9097 High Similarity NPC472515
0.9097 High Similarity NPC136095
0.9091 High Similarity NPC253616
0.9091 High Similarity NPC216092
0.9085 High Similarity NPC33320
0.9067 High Similarity NPC98028
0.9032 High Similarity NPC234536
0.9032 High Similarity NPC78612
0.9028 High Similarity NPC36414
0.9021 High Similarity NPC268081
0.9021 High Similarity NPC472516
0.898 High Similarity NPC17262
0.8958 High Similarity NPC103001
0.8954 High Similarity NPC247677
0.8954 High Similarity NPC160015
0.894 High Similarity NPC116604
0.8933 High Similarity NPC226644
0.8933 High Similarity NPC37226
0.8917 High Similarity NPC179015
0.8917 High Similarity NPC173149
0.8903 High Similarity NPC115432
0.8903 High Similarity NPC260296
0.8896 High Similarity NPC260902
0.8896 High Similarity NPC296957
0.8889 High Similarity NPC29638
0.8882 High Similarity NPC67654
0.8839 High Similarity NPC476350
0.8839 High Similarity NPC476349
0.8839 High Similarity NPC244750
0.8836 High Similarity NPC473209
0.8831 High Similarity NPC470625
0.8824 High Similarity NPC1477
0.8824 High Similarity NPC213608
0.8824 High Similarity NPC122365
0.882 High Similarity NPC72455
0.882 High Similarity NPC233956
0.8816 High Similarity NPC156244
0.8816 High Similarity NPC290671
0.8816 High Similarity NPC170169
0.8812 High Similarity NPC144288
0.8808 High Similarity NPC39929
0.8808 High Similarity NPC296030
0.8808 High Similarity NPC317492
0.8803 High Similarity NPC175159
0.88 High Similarity NPC130581
0.88 High Similarity NPC12148
0.8792 High Similarity NPC171656
0.879 High Similarity NPC193998
0.8774 High Similarity NPC65504
0.8766 High Similarity NPC198490
0.8766 High Similarity NPC474542
0.8759 High Similarity NPC254741
0.8758 High Similarity NPC5871
0.8758 High Similarity NPC253872
0.875 High Similarity NPC230713
0.875 High Similarity NPC78335
0.8742 High Similarity NPC323137
0.8742 High Similarity NPC135325
0.8742 High Similarity NPC168085
0.8734 High Similarity NPC65846
0.8734 High Similarity NPC155640
0.8733 High Similarity NPC210826
0.8733 High Similarity NPC300267
0.8733 High Similarity NPC51641
0.8732 High Similarity NPC472517
0.8726 High Similarity NPC264293
0.8725 High Similarity NPC302181
0.8725 High Similarity NPC184702
0.8725 High Similarity NPC225884
0.8716 High Similarity NPC297985
0.8712 High Similarity NPC107244
0.8712 High Similarity NPC325176
0.8701 High Similarity NPC183874
0.8701 High Similarity NPC472462
0.8699 High Similarity NPC38153
0.8696 High Similarity NPC281835
0.8696 High Similarity NPC51404
0.8688 High Similarity NPC320789
0.8684 High Similarity NPC164299
0.8684 High Similarity NPC178202
0.8684 High Similarity NPC221868
0.8684 High Similarity NPC37208
0.8681 High Similarity NPC247743
0.8681 High Similarity NPC292998
0.8679 High Similarity NPC204088
0.8679 High Similarity NPC259007
0.8679 High Similarity NPC329215
0.8675 High Similarity NPC17816
0.8667 High Similarity NPC230943
0.8667 High Similarity NPC179970
0.8667 High Similarity NPC294365
0.8658 High Similarity NPC53192
0.865 High Similarity NPC224165
0.865 High Similarity NPC53917
0.8645 High Similarity NPC148938
0.8645 High Similarity NPC108937
0.8645 High Similarity NPC279218
0.8636 High Similarity NPC41326
0.8634 High Similarity NPC41853
0.863 High Similarity NPC161196
0.8627 High Similarity NPC474735
0.8621 High Similarity NPC66705
0.8621 High Similarity NPC229128
0.8618 High Similarity NPC272194
0.8616 High Similarity NPC15819
0.8611 High Similarity NPC55147
0.8611 High Similarity NPC229646
0.8611 High Similarity NPC54503
0.8611 High Similarity NPC182428
0.8609 High Similarity NPC470322
0.8609 High Similarity NPC154217
0.8609 High Similarity NPC473927
0.8608 High Similarity NPC304387
0.86 High Similarity NPC470932
0.8599 High Similarity NPC40583
0.8591 High Similarity NPC22467
0.859 High Similarity NPC474609
0.859 High Similarity NPC469936
0.859 High Similarity NPC78554
0.859 High Similarity NPC321372
0.859 High Similarity NPC474738
0.859 High Similarity NPC19860
0.859 High Similarity NPC129053
0.859 High Similarity NPC109967
0.859 High Similarity NPC475797
0.8581 High Similarity NPC11566
0.8581 High Similarity NPC186507
0.8581 High Similarity NPC235333
0.8581 High Similarity NPC137009
0.858 High Similarity NPC120220
0.8571 High Similarity NPC259685
0.8571 High Similarity NPC318424
0.8571 High Similarity NPC167479
0.8571 High Similarity NPC332594
0.8571 High Similarity NPC115324
0.8562 High Similarity NPC38914
0.8562 High Similarity NPC46869
0.8562 High Similarity NPC136641
0.8553 High Similarity NPC218300
0.8553 High Similarity NPC219861
0.8553 High Similarity NPC282335
0.8553 High Similarity NPC471285
0.8552 High Similarity NPC223354
0.8544 High Similarity NPC74749
0.8544 High Similarity NPC19554
0.8544 High Similarity NPC43971
0.8543 High Similarity NPC311741
0.8543 High Similarity NPC469953
0.8543 High Similarity NPC196137
0.8543 High Similarity NPC1886
0.8543 High Similarity NPC234629
0.8543 High Similarity NPC155144
0.8543 High Similarity NPC98926
0.8542 High Similarity NPC278556
0.8542 High Similarity NPC284424
0.8535 High Similarity NPC212967
0.8535 High Similarity NPC246647

  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 NPC88445 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
0.9859 High Similarity NPD920 Approved
0.9718 High Similarity NPD642 Clinical (unspecified phase)
0.9577 High Similarity NPD643 Clinical (unspecified phase)
0.9366 High Similarity NPD1243 Approved
0.9085 High Similarity NPD919 Approved
0.8726 High Similarity NPD1247 Approved
0.863 High Similarity NPD2796 Approved
0.8421 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8418 Intermediate Similarity NPD3749 Approved
0.8355 Intermediate Similarity NPD6799 Approved
0.8344 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD7819 Suspended
0.8333 Intermediate Similarity NPD7411 Suspended
0.828 Intermediate Similarity NPD6801 Discontinued
0.82 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.8199 Intermediate Similarity NPD5494 Approved
0.8188 Intermediate Similarity NPD1510 Phase 2
0.8188 Intermediate Similarity NPD3748 Approved
0.8187 Intermediate Similarity NPD7075 Discontinued
0.8153 Intermediate Similarity NPD6599 Discontinued
0.8146 Intermediate Similarity NPD1549 Phase 2
0.8144 Intermediate Similarity NPD6559 Discontinued
0.8133 Intermediate Similarity NPD1551 Phase 2
0.8092 Intermediate Similarity NPD2800 Approved
0.8079 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8079 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8065 Intermediate Similarity NPD2532 Approved
0.8065 Intermediate Similarity NPD2534 Approved
0.8065 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8065 Intermediate Similarity NPD2533 Approved
0.8063 Intermediate Similarity NPD3817 Phase 2
0.8041 Intermediate Similarity NPD1240 Approved
0.8038 Intermediate Similarity NPD4380 Phase 2
0.8027 Intermediate Similarity NPD2313 Discontinued
0.8014 Intermediate Similarity NPD6832 Phase 2
0.8012 Intermediate Similarity NPD7768 Phase 2
0.8 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7974 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7961 Intermediate Similarity NPD2344 Approved
0.7947 Intermediate Similarity NPD2799 Discontinued
0.7939 Intermediate Similarity NPD3926 Phase 2
0.7933 Intermediate Similarity NPD1607 Approved
0.7922 Intermediate Similarity NPD3750 Approved
0.7922 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7908 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7905 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7904 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7901 Intermediate Similarity NPD3882 Suspended
0.7867 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.784 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7834 Intermediate Similarity NPD5401 Approved
0.7826 Intermediate Similarity NPD1934 Approved
0.7798 Intermediate Similarity NPD3818 Discontinued
0.7778 Intermediate Similarity NPD2801 Approved
0.7778 Intermediate Similarity NPD2935 Discontinued
0.7771 Intermediate Similarity NPD1511 Approved
0.7765 Intermediate Similarity NPD5953 Discontinued
0.7756 Intermediate Similarity NPD2309 Approved
0.7755 Intermediate Similarity NPD1019 Discontinued
0.7751 Intermediate Similarity NPD7286 Phase 2
0.775 Intermediate Similarity NPD3226 Approved
0.7736 Intermediate Similarity NPD5403 Approved
0.773 Intermediate Similarity NPD5402 Approved
0.7673 Intermediate Similarity NPD1512 Approved
0.7667 Intermediate Similarity NPD1296 Phase 2
0.7665 Intermediate Similarity NPD6232 Discontinued
0.7665 Intermediate Similarity NPD6808 Phase 2
0.7647 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD5844 Phase 1
0.7633 Intermediate Similarity NPD7473 Discontinued
0.7625 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD2346 Discontinued
0.7613 Intermediate Similarity NPD1471 Phase 3
0.7605 Intermediate Similarity NPD6959 Discontinued
0.7603 Intermediate Similarity NPD9717 Approved
0.7576 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD3266 Approved
0.7568 Intermediate Similarity NPD3267 Approved
0.7568 Intermediate Similarity NPD1203 Approved
0.7566 Intermediate Similarity NPD4307 Phase 2
0.7534 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD2654 Approved
0.75 Intermediate Similarity NPD6280 Approved
0.75 Intermediate Similarity NPD6279 Approved
0.7471 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD4628 Phase 3
0.7456 Intermediate Similarity NPD7229 Phase 3
0.7456 Intermediate Similarity NPD5710 Approved
0.7456 Intermediate Similarity NPD5711 Approved
0.7416 Intermediate Similarity NPD4287 Approved
0.7415 Intermediate Similarity NPD422 Phase 1
0.7403 Intermediate Similarity NPD1933 Approved
0.7403 Intermediate Similarity NPD447 Suspended
0.7401 Intermediate Similarity NPD8434 Phase 2
0.7381 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD4308 Phase 3
0.7372 Intermediate Similarity NPD7033 Discontinued
0.7371 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6166 Phase 2
0.7368 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD6651 Approved
0.7349 Intermediate Similarity NPD1465 Phase 2
0.7341 Intermediate Similarity NPD7054 Approved
0.7333 Intermediate Similarity NPD5889 Approved
0.7333 Intermediate Similarity NPD5890 Approved
0.732 Intermediate Similarity NPD3268 Approved
0.7303 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD7472 Approved
0.7299 Intermediate Similarity NPD7074 Phase 3
0.729 Intermediate Similarity NPD230 Phase 1
0.729 Intermediate Similarity NPD5124 Phase 1
0.729 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD2798 Approved
0.7279 Intermediate Similarity NPD17 Approved
0.7273 Intermediate Similarity NPD1241 Discontinued
0.7267 Intermediate Similarity NPD2403 Approved
0.7257 Intermediate Similarity NPD6797 Phase 2
0.7229 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD2797 Approved
0.7216 Intermediate Similarity NPD7251 Discontinued
0.7208 Intermediate Similarity NPD411 Approved
0.7202 Intermediate Similarity NPD4288 Approved
0.7202 Intermediate Similarity NPD2296 Approved
0.72 Intermediate Similarity NPD1729 Discontinued
0.7175 Intermediate Similarity NPD7808 Phase 3
0.7169 Intermediate Similarity NPD6585 Discontinued
0.7168 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD3225 Approved
0.7152 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5760 Phase 2
0.7143 Intermediate Similarity NPD9545 Approved
0.7143 Intermediate Similarity NPD5761 Phase 2
0.7133 Intermediate Similarity NPD1608 Approved
0.7133 Intermediate Similarity NPD3972 Approved
0.7115 Intermediate Similarity NPD943 Approved
0.711 Intermediate Similarity NPD5242 Approved
0.7099 Intermediate Similarity NPD3887 Approved
0.7097 Intermediate Similarity NPD3764 Approved
0.7081 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD2353 Approved
0.7063 Intermediate Similarity NPD6002 Phase 3
0.7063 Intermediate Similarity NPD6005 Phase 3
0.7063 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD6004 Phase 3
0.7063 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD1876 Approved
0.7027 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD4361 Phase 2
0.7007 Intermediate Similarity NPD9493 Approved
0.7006 Intermediate Similarity NPD7458 Discontinued
0.7006 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD2979 Phase 3
0.7 Intermediate Similarity NPD5353 Approved
0.6994 Remote Similarity NPD7199 Phase 2
0.6993 Remote Similarity NPD1164 Approved
0.6987 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6987 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6975 Remote Similarity NPD1652 Phase 2
0.6973 Remote Similarity NPD4363 Phase 3
0.6973 Remote Similarity NPD4360 Phase 2
0.6962 Remote Similarity NPD6355 Discontinued
0.6957 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6954 Remote Similarity NPD1281 Approved
0.694 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6933 Remote Similarity NPD7003 Approved
0.6928 Remote Similarity NPD6273 Approved
0.6923 Remote Similarity NPD6386 Approved
0.6923 Remote Similarity NPD6385 Approved
0.6914 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6914 Remote Similarity NPD2424 Discontinued
0.6913 Remote Similarity NPD1548 Phase 1
0.6909 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6909 Remote Similarity NPD7390 Discontinued
0.6901 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6899 Remote Similarity NPD3142 Approved
0.6899 Remote Similarity NPD3140 Approved
0.6894 Remote Similarity NPD4476 Approved
0.6894 Remote Similarity NPD4477 Approved
0.6893 Remote Similarity NPD3751 Discontinued
0.689 Remote Similarity NPD2354 Approved
0.6882 Remote Similarity NPD37 Approved
0.6879 Remote Similarity NPD6798 Discontinued
0.6867 Remote Similarity NPD5691 Approved
0.686 Remote Similarity NPD4965 Approved
0.686 Remote Similarity NPD4967 Phase 2
0.686 Remote Similarity NPD4966 Approved
0.6859 Remote Similarity NPD4908 Phase 1
0.6851 Remote Similarity NPD8312 Approved
0.6851 Remote Similarity NPD8313 Approved
0.6849 Remote Similarity NPD5535 Approved
0.6842 Remote Similarity NPD1611 Approved
0.6842 Remote Similarity NPD1610 Phase 2
0.6842 Remote Similarity NPD8455 Phase 2

  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