Structure

Physi-Chem Properties

Molecular Weight:  358.14
Volume:  357.173
LogP:  2.08
LogD:  2.62
LogS:  -4.024
# Rotatable Bonds:  4
TPSA:  77.38
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.874
Synthetic Accessibility Score:  3.679
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.849
MDCK Permeability:  1.509168214397505e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.323
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.014
30% Bioavailability (F30%):  0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.015
Plasma Protein Binding (PPB):  94.6217269897461%
Volume Distribution (VD):  0.57
Pgp-substrate:  6.732779026031494%

ADMET: Metabolism

CYP1A2-inhibitor:  0.053
CYP1A2-substrate:  0.881
CYP2C19-inhibitor:  0.11
CYP2C19-substrate:  0.659
CYP2C9-inhibitor:  0.436
CYP2C9-substrate:  0.714
CYP2D6-inhibitor:  0.379
CYP2D6-substrate:  0.82
CYP3A4-inhibitor:  0.321
CYP3A4-substrate:  0.587

ADMET: Excretion

Clearance (CL):  5.662
Half-life (T1/2):  0.644

ADMET: Toxicity

hERG Blockers:  0.348
Human Hepatotoxicity (H-HT):  0.238
Drug-inuced Liver Injury (DILI):  0.847
AMES Toxicity:  0.227
Rat Oral Acute Toxicity:  0.145
Maximum Recommended Daily Dose:  0.842
Skin Sensitization:  0.943
Carcinogencity:  0.14
Eye Corrosion:  0.004
Eye Irritation:  0.91
Respiratory Toxicity:  0.86

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General Info & Identifiers & Properties  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC115207

Natural Product ID:  NPC115207
Common Name*:   (-)-Pinoresinol
IUPAC Name:   4-[(3R,3aR,6R,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
Synonyms:   (-)-Pinoresinol
Standard InCHIKey:  HGXBRUKMWQGOIE-FEBSWUBLSA-N
Standard InCHI:  InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3/t13-,14-,19-,20-/m0/s1
SMILES:  COc1cc(ccc1O)[C@@H]1OC[C@H]2[C@@H]1CO[C@H]2c1ccc(c(c1)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL460862
PubChem CID:   12309637
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003686] Furanoid lignans

*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
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seeds n.a. DOI[10.1002/ejlt.201100207]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. fruit n.a. DOI[10.1007/s00217-007-0799-1]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11746-997-0093-1]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. flower n.a. DOI[10.1016/j.foodchem.2011.01.077]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seeds n.a. DOI[10.5219/332]
NPO13757 Coptis japonica Species Ranunculaceae Eukaryota rhizomes n.a. n.a. PMID[11000020]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. leaf n.a. PMID[11348221]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[11520216]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. seed n.a. PMID[11540412]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. tuber n.a. PMID[12913245]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[1293938]
NPO9642 Brassica fruticulosa Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[14518939]
NPO19805 Forsythia viridissima Species Oleaceae Eukaryota n.a. flower n.a. PMID[15481244]
NPO21349 Punica granatum Species Lythraceae Eukaryota Seeds n.a. n.a. PMID[15620261]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruit n.a. n.a. PMID[15844957]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[16181762]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruits n.a. n.a. PMID[16378361]
NPO17434 Sambucus williamsii Species Adoxaceae Eukaryota n.a. stem n.a. PMID[16651764]
NPO2211 Solanum nigrum Species Solanaceae Eukaryota Whole plant n.a. steroidal saponins PMID[16933867]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. PMID[17156960]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruits Tahiti n.a. PMID[17378609]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[17480098]
NPO7490 Aconitum japonicum Species Ranunculaceae Eukaryota roots n.a. n.a. PMID[18044843]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota roots n.a. n.a. PMID[18076142]
NPO12339 Daphne feddei Species Thymelaeaceae Eukaryota stem bark Kunming, Yunnan Province, China n.a. PMID[18986199]
NPO17039 Pharbitis nil Species Convolvulaceae Eukaryota Seeds n.a. n.a. PMID[19435339]
NPO4001 Berberis koreana Species Berberidaceae Eukaryota n.a. n.a. n.a. PMID[19813743]
NPO13757 Coptis japonica Species Ranunculaceae Eukaryota n.a. rhizome n.a. PMID[21401114]
NPO4001 Berberis koreana Species Berberidaceae Eukaryota trunk Jeju island, Korea 2005-Dec PMID[21420296]
NPO4001 Berberis koreana Species Berberidaceae Eukaryota n.a. n.a. n.a. PMID[21420296]
NPO2462 Machilus robusta Species Lauraceae Eukaryota bark n.a. n.a. PMID[21627109]
NPO2462 Machilus robusta Species Lauraceae Eukaryota n.a. bark n.a. PMID[21627109]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. flower n.a. PMID[21916433]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[22223386]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. PMID[22537213]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota Lateral roots n.a. n.a. PMID[22607495]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[22628040]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[22907155]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[23225552]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota flower buds n.a. n.a. PMID[23558238]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[23707213]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[23707213]
NPO7490 Aconitum japonicum Species Ranunculaceae Eukaryota n.a. root n.a. PMID[24190290]
NPO7490 Aconitum japonicum Species Ranunculaceae Eukaryota n.a. leaf n.a. PMID[24190290]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[24224843]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. PMID[24417583]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[24793215]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. PMID[26422318]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seeds n.a. n.a. PMID[26923696]
NPO17434 Sambucus williamsii Species Adoxaceae Eukaryota n.a. n.a. n.a. PMID[26988298]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[27196335]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[27228307]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[27761113]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota Fruits n.a. n.a. PMID[28218000]
NPO19805 Forsythia viridissima Species Oleaceae Eukaryota Roots n.a. n.a. PMID[30676026]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota Roots n.a. n.a. PMID[30892884]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota Roots n.a. n.a. PMID[31150241]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[31860304]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota Roots n.a. n.a. PMID[32004936]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[32083868]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[32223193]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seed Oil n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Stem Bark n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Twig n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Root Bark n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. Database[FooDB]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. Database[FooDB]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14108 Nardostachys jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19805 Forsythia viridissima Species Oleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7490 Aconitum japonicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2211 Solanum nigrum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13757 Coptis japonica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17434 Sambucus williamsii Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5649 Coptis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22622 Coptis deltoidea Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO21349 Punica granatum Species Lythraceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO19805 Forsythia viridissima Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22622 Coptis deltoidea Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5649 Coptis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12128 Ipomoea purpurea Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2211 Solanum nigrum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9069 Persicaria tinctoria Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17039 Pharbitis nil Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17434 Sambucus williamsii Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13757 Coptis japonica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14108 Nardostachys jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7490 Aconitum japonicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14108 Nardostachys jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5649 Coptis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2211 Solanum nigrum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14108 Nardostachys jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23035 Clematis montana Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17039 Pharbitis nil Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7490 Aconitum japonicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2211 Solanum nigrum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17434 Sambucus williamsii Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9069 Persicaria tinctoria Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5649 Coptis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22622 Coptis deltoidea Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22589 Clematis armandii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12128 Ipomoea purpurea Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29008 Coptis teeta Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13757 Coptis japonica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19805 Forsythia viridissima Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2462 Machilus robusta Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12128 Ipomoea purpurea Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17434 Sambucus williamsii Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4001 Berberis koreana Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14108 Nardostachys jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29008 Coptis teeta Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12339 Daphne feddei Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22622 Coptis deltoidea Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13757 Coptis japonica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5649 Coptis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7490 Aconitum japonicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9069 Persicaria tinctoria Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9642 Brassica fruticulosa Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2211 Solanum nigrum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17039 Pharbitis nil Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9756 Daphne genkwa Species Thymelaeaceae 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
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens IC50 = 13800.0 nM PMID[468441]
NPT257 Individual Protein Arachidonate 15-lipoxygenase Oryctolagus cuniculus IC50 = 3500.0 nM PMID[468441]
NPT31 Individual Protein Cyclooxygenase-2 Homo sapiens IC50 > 100000.0 nM PMID[468441]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 266000.0 nM PMID[468443]
NPT34 Cell Line BV-2 Mus musculus IC50 = 26190.0 nM PMID[468444]
NPT81 Cell Line A549 Homo sapiens IC50 > 30000.0 nM PMID[468444]
NPT147 Cell Line SK-MEL-2 Homo sapiens IC50 = 26600.0 nM PMID[468444]
NPT574 Cell Line XF498 Homo sapiens IC50 = 13320.0 nM PMID[468444]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 > 30000.0 nM PMID[468444]
NPT681 Cell Line PC-12 Rattus norvegicus Activity = 73.2 % PMID[468445]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 = 18690.0 nM PMID[468447]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 10.0 ug.mL-1 PMID[468442]

☑ 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 NPC115207 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 NPC27843
1.0 High Similarity NPC158079
1.0 High Similarity NPC40432
1.0 High Similarity NPC228346
1.0 High Similarity NPC161557
1.0 High Similarity NPC7171
0.992 High Similarity NPC181049
0.992 High Similarity NPC207400
0.9762 High Similarity NPC4940
0.976 High Similarity NPC241522
0.976 High Similarity NPC42300
0.976 High Similarity NPC257582
0.976 High Similarity NPC153739
0.976 High Similarity NPC242807
0.976 High Similarity NPC77040
0.976 High Similarity NPC145305
0.976 High Similarity NPC174495
0.976 High Similarity NPC64201
0.976 High Similarity NPC187998
0.976 High Similarity NPC92164
0.9758 High Similarity NPC11258
0.9758 High Similarity NPC184733
0.9758 High Similarity NPC128208
0.9758 High Similarity NPC129570
0.9758 High Similarity NPC282703
0.9758 High Similarity NPC45774
0.9758 High Similarity NPC21867
0.9688 High Similarity NPC99572
0.9688 High Similarity NPC126409
0.9683 High Similarity NPC277804
0.968 High Similarity NPC475875
0.96 High Similarity NPC470084
0.9535 High Similarity NPC142547
0.9535 High Similarity NPC141765
0.9535 High Similarity NPC135777
0.9535 High Similarity NPC165155
0.9535 High Similarity NPC24490
0.9535 High Similarity NPC34103
0.9531 High Similarity NPC158331
0.952 High Similarity NPC165045
0.952 High Similarity NPC118533
0.9466 High Similarity NPC123526
0.9466 High Similarity NPC88640
0.9466 High Similarity NPC193666
0.9457 High Similarity NPC67247
0.9457 High Similarity NPC287745
0.9453 High Similarity NPC175067
0.9453 High Similarity NPC204215
0.944 High Similarity NPC206882
0.9435 High Similarity NPC257682
0.9435 High Similarity NPC121783
0.9435 High Similarity NPC34902
0.9435 High Similarity NPC131747
0.9435 High Similarity NPC18449
0.9435 High Similarity NPC146355
0.9365 High Similarity NPC5428
0.936 High Similarity NPC148627
0.9355 High Similarity NPC31344
0.9355 High Similarity NPC317769
0.9313 High Similarity NPC54743
0.9313 High Similarity NPC156502
0.9313 High Similarity NPC471988
0.9313 High Similarity NPC177160
0.9313 High Similarity NPC10737
0.9313 High Similarity NPC209985
0.9313 High Similarity NPC263367
0.9313 High Similarity NPC477939
0.9313 High Similarity NPC29799
0.9308 High Similarity NPC49603
0.9308 High Similarity NPC326095
0.9308 High Similarity NPC471942
0.9308 High Similarity NPC193026
0.9308 High Similarity NPC187616
0.9308 High Similarity NPC244983
0.9302 High Similarity NPC471505
0.9291 High Similarity NPC252307
0.9291 High Similarity NPC245826
0.9291 High Similarity NPC474178
0.9248 High Similarity NPC177868
0.9248 High Similarity NPC55793
0.9242 High Similarity NPC281780
0.9237 High Similarity NPC184938
0.9237 High Similarity NPC101624
0.9225 High Similarity NPC474017
0.9213 High Similarity NPC292056
0.9213 High Similarity NPC118787
0.9213 High Similarity NPC147821
0.9213 High Similarity NPC111247
0.9213 High Similarity NPC163332
0.9213 High Similarity NPC183181
0.9213 High Similarity NPC41706
0.9213 High Similarity NPC319625
0.92 High Similarity NPC471693
0.92 High Similarity NPC280704
0.92 High Similarity NPC473451
0.9194 High Similarity NPC126935
0.9194 High Similarity NPC57268
0.9194 High Similarity NPC312713
0.9194 High Similarity NPC172676
0.9194 High Similarity NPC65933
0.9194 High Similarity NPC216929
0.9185 High Similarity NPC477898
0.9185 High Similarity NPC298317
0.9185 High Similarity NPC255566
0.9185 High Similarity NPC265154
0.9167 High Similarity NPC77861
0.9154 High Similarity NPC259742
0.9154 High Similarity NPC219671
0.9154 High Similarity NPC147616
0.9154 High Similarity NPC106739
0.9154 High Similarity NPC104077
0.9141 High Similarity NPC222127
0.9141 High Similarity NPC82862
0.9134 High Similarity NPC58607
0.9134 High Similarity NPC178284
0.9134 High Similarity NPC191037
0.912 High Similarity NPC85488
0.9118 High Similarity NPC470097
0.9118 High Similarity NPC84181
0.9118 High Similarity NPC114119
0.9118 High Similarity NPC471415
0.9104 High Similarity NPC160283
0.9104 High Similarity NPC254759
0.9104 High Similarity NPC184797
0.9104 High Similarity NPC309124
0.9091 High Similarity NPC18576
0.9084 High Similarity NPC26394
0.9084 High Similarity NPC169973
0.907 High Similarity NPC170844
0.907 High Similarity NPC476968
0.907 High Similarity NPC5851
0.907 High Similarity NPC86030
0.9062 High Similarity NPC8050
0.9062 High Similarity NPC473093
0.9062 High Similarity NPC473092
0.9062 High Similarity NPC127587
0.9055 High Similarity NPC194519
0.9051 High Similarity NPC279298
0.9051 High Similarity NPC223185
0.9051 High Similarity NPC22150
0.9051 High Similarity NPC38041
0.9044 High Similarity NPC12728
0.9044 High Similarity NPC185071
0.904 High Similarity NPC262156
0.904 High Similarity NPC470804
0.904 High Similarity NPC184651
0.904 High Similarity NPC324571
0.904 High Similarity NPC343720
0.904 High Similarity NPC54872
0.904 High Similarity NPC470212
0.904 High Similarity NPC473853
0.904 High Similarity NPC476343
0.904 High Similarity NPC312675
0.904 High Similarity NPC113865
0.9037 High Similarity NPC87725
0.9037 High Similarity NPC472711
0.9037 High Similarity NPC471414
0.9037 High Similarity NPC263261
0.9032 High Similarity NPC95614
0.9032 High Similarity NPC227217
0.9032 High Similarity NPC56214
0.9032 High Similarity NPC232316
0.9032 High Similarity NPC242885
0.9032 High Similarity NPC165133
0.9032 High Similarity NPC117780
0.903 High Similarity NPC236306
0.903 High Similarity NPC292882
0.903 High Similarity NPC473739
0.903 High Similarity NPC232164
0.9015 High Similarity NPC47181
0.9015 High Similarity NPC478085
0.9008 High Similarity NPC253105
0.9008 High Similarity NPC201587
0.9008 High Similarity NPC230219
0.9 High Similarity NPC275950
0.9 High Similarity NPC173308
0.9 High Similarity NPC143483
0.9 High Similarity NPC181079
0.8992 High Similarity NPC165128
0.8992 High Similarity NPC186843
0.8992 High Similarity NPC54321
0.8992 High Similarity NPC98631
0.8992 High Similarity NPC57119
0.8992 High Similarity NPC328682
0.8992 High Similarity NPC158471
0.8992 High Similarity NPC470213
0.8992 High Similarity NPC226862
0.8992 High Similarity NPC206615
0.8992 High Similarity NPC72529
0.8992 High Similarity NPC281864
0.8986 High Similarity NPC317053
0.8986 High Similarity NPC112861
0.8986 High Similarity NPC324492
0.8984 High Similarity NPC50683
0.8984 High Similarity NPC112571
0.8984 High Similarity NPC76451
0.8984 High Similarity NPC285725
0.8976 High Similarity NPC293701
0.8976 High Similarity NPC94276
0.8976 High Similarity NPC48990

  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 NPC115207 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
0.907 High Similarity NPD3027 Phase 3
0.8468 Intermediate Similarity NPD5283 Phase 1
0.8444 Intermediate Similarity NPD1613 Approved
0.8444 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8306 Intermediate Similarity NPD228 Approved
0.8284 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8209 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8209 Intermediate Similarity NPD2861 Phase 2
0.8175 Intermediate Similarity NPD3620 Phase 2
0.8175 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.8168 Intermediate Similarity NPD3705 Approved
0.8146 Intermediate Similarity NPD6234 Discontinued
0.8145 Intermediate Similarity NPD3021 Approved
0.8145 Intermediate Similarity NPD3022 Approved
0.8045 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD4966 Approved
0.7895 Intermediate Similarity NPD4967 Phase 2
0.7895 Intermediate Similarity NPD4965 Approved
0.7883 Intermediate Similarity NPD4908 Phase 1
0.7803 Intermediate Similarity NPD1357 Approved
0.7786 Intermediate Similarity NPD1558 Phase 1
0.7786 Intermediate Similarity NPD4060 Phase 1
0.7785 Intermediate Similarity NPD7228 Approved
0.7778 Intermediate Similarity NPD2982 Phase 2
0.7778 Intermediate Similarity NPD2983 Phase 2
0.777 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7761 Intermediate Similarity NPD1610 Phase 2
0.7755 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD4236 Phase 3
0.7724 Intermediate Similarity NPD4237 Approved
0.7708 Intermediate Similarity NPD7266 Discontinued
0.7704 Intermediate Similarity NPD2981 Phase 2
0.7697 Intermediate Similarity NPD1934 Approved
0.7697 Intermediate Similarity NPD37 Approved
0.7681 Intermediate Similarity NPD3018 Phase 2
0.7647 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7638 Intermediate Similarity NPD2684 Approved
0.7634 Intermediate Similarity NPD7157 Approved
0.7606 Intermediate Similarity NPD5735 Approved
0.7603 Intermediate Similarity NPD6674 Discontinued
0.7603 Intermediate Similarity NPD3060 Approved
0.7603 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7569 Intermediate Similarity NPD5588 Approved
0.7551 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD6331 Phase 2
0.7551 Intermediate Similarity NPD4110 Phase 3
0.7548 Intermediate Similarity NPD3882 Suspended
0.7538 Intermediate Similarity NPD7843 Approved
0.7532 Intermediate Similarity NPD2977 Approved
0.7532 Intermediate Similarity NPD2978 Approved
0.7532 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD5536 Phase 2
0.7517 Intermediate Similarity NPD2161 Phase 2
0.75 Intermediate Similarity NPD4538 Approved
0.75 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4536 Approved
0.75 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD6355 Discontinued
0.7468 Intermediate Similarity NPD7199 Phase 2
0.7466 Intermediate Similarity NPD1375 Discontinued
0.7463 Intermediate Similarity NPD1548 Phase 1
0.745 Intermediate Similarity NPD5058 Phase 3
0.7419 Intermediate Similarity NPD3020 Approved
0.7419 Intermediate Similarity NPD2801 Approved
0.7413 Intermediate Similarity NPD2238 Phase 2
0.741 Intermediate Similarity NPD3094 Phase 2
0.741 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD5111 Phase 2
0.7394 Intermediate Similarity NPD5109 Approved
0.7394 Intermediate Similarity NPD5110 Phase 2
0.7391 Intermediate Similarity NPD4749 Approved
0.7375 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD1091 Approved
0.7368 Intermediate Similarity NPD6671 Approved
0.7365 Intermediate Similarity NPD5177 Phase 3
0.7361 Intermediate Similarity NPD3657 Discovery
0.7357 Intermediate Similarity NPD6584 Phase 3
0.7351 Intermediate Similarity NPD4123 Phase 3
0.7347 Intermediate Similarity NPD5762 Approved
0.7347 Intermediate Similarity NPD5763 Approved
0.7346 Intermediate Similarity NPD3818 Discontinued
0.7344 Intermediate Similarity NPD968 Approved
0.7343 Intermediate Similarity NPD2674 Phase 3
0.7338 Intermediate Similarity NPD8651 Approved
0.7329 Intermediate Similarity NPD5960 Phase 3
0.7329 Intermediate Similarity NPD6166 Phase 2
0.7329 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD7095 Approved
0.7324 Intermediate Similarity NPD4625 Phase 3
0.732 Intermediate Similarity NPD1653 Approved
0.7315 Intermediate Similarity NPD4628 Phase 3
0.731 Intermediate Similarity NPD6653 Approved
0.7303 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD290 Approved
0.7273 Intermediate Similarity NPD3145 Approved
0.7273 Intermediate Similarity NPD3144 Approved
0.7273 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7240 Approved
0.7267 Intermediate Similarity NPD2677 Approved
0.7267 Intermediate Similarity NPD6190 Approved
0.7266 Intermediate Similarity NPD5327 Phase 3
0.7261 Intermediate Similarity NPD2560 Approved
0.7261 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD2563 Approved
0.7254 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD4162 Approved
0.7246 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD3092 Approved
0.7237 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD5846 Approved
0.7226 Intermediate Similarity NPD4675 Approved
0.7226 Intermediate Similarity NPD5126 Approved
0.7226 Intermediate Similarity NPD5125 Phase 3
0.7226 Intermediate Similarity NPD4678 Approved
0.7226 Intermediate Similarity NPD6516 Phase 2
0.7222 Intermediate Similarity NPD27 Approved
0.7222 Intermediate Similarity NPD6233 Phase 2
0.7222 Intermediate Similarity NPD2489 Approved
0.7222 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD7124 Phase 2
0.7214 Intermediate Similarity NPD6696 Suspended
0.7211 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD4210 Discontinued
0.7197 Intermediate Similarity NPD5772 Approved
0.7197 Intermediate Similarity NPD5773 Approved
0.7194 Intermediate Similarity NPD2230 Approved
0.7194 Intermediate Similarity NPD2235 Phase 2
0.7194 Intermediate Similarity NPD1608 Approved
0.7194 Intermediate Similarity NPD2233 Approved
0.7194 Intermediate Similarity NPD2231 Phase 2
0.7194 Intermediate Similarity NPD2232 Approved
0.7192 Intermediate Similarity NPD6353 Approved
0.719 Intermediate Similarity NPD52 Approved
0.719 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD7526 Approved
0.7188 Intermediate Similarity NPD5494 Approved
0.7186 Intermediate Similarity NPD7312 Approved
0.7186 Intermediate Similarity NPD7313 Approved
0.7186 Intermediate Similarity NPD7311 Approved
0.7186 Intermediate Similarity NPD7310 Approved
0.7183 Intermediate Similarity NPD9494 Approved
0.7177 Intermediate Similarity NPD2860 Approved
0.7177 Intermediate Similarity NPD2859 Approved
0.7172 Intermediate Similarity NPD4140 Approved
0.7172 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD1511 Approved
0.7171 Intermediate Similarity NPD4357 Discontinued
0.717 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD7685 Pre-registration
0.7165 Intermediate Similarity NPD291 Approved
0.7161 Intermediate Similarity NPD4005 Discontinued
0.716 Intermediate Similarity NPD2969 Approved
0.716 Intermediate Similarity NPD2970 Approved
0.7153 Intermediate Similarity NPD6798 Discontinued
0.7152 Intermediate Similarity NPD7074 Phase 3
0.7152 Intermediate Similarity NPD5241 Discontinued
0.7143 Intermediate Similarity NPD6583 Phase 3
0.7143 Intermediate Similarity NPD7309 Approved
0.7143 Intermediate Similarity NPD6582 Phase 2
0.7143 Intermediate Similarity NPD6895 Approved
0.7143 Intermediate Similarity NPD6896 Approved
0.7114 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD3540 Phase 1
0.7114 Intermediate Similarity NPD6004 Phase 3
0.7114 Intermediate Similarity NPD6005 Phase 3
0.7114 Intermediate Similarity NPD6002 Phase 3
0.7114 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD4624 Approved
0.7101 Intermediate Similarity NPD2667 Approved
0.7101 Intermediate Similarity NPD2668 Approved
0.7099 Intermediate Similarity NPD3051 Approved
0.7097 Intermediate Similarity NPD2933 Approved
0.7097 Intermediate Similarity NPD9296 Approved
0.7097 Intermediate Similarity NPD3687 Approved
0.7097 Intermediate Similarity NPD2934 Approved
0.7097 Intermediate Similarity NPD3686 Approved
0.7091 Intermediate Similarity NPD7054 Approved
0.7089 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD4578 Approved
0.7083 Intermediate Similarity NPD4577 Approved
0.708 Intermediate Similarity NPD3091 Approved
0.708 Intermediate Similarity NPD1182 Approved
0.7078 Intermediate Similarity NPD1512 Approved
0.7071 Intermediate Similarity NPD1840 Phase 2
0.7067 Intermediate Similarity NPD7037 Approved
0.7059 Intermediate Similarity NPD4663 Approved
0.7055 Intermediate Similarity NPD3062 Approved
0.7055 Intermediate Similarity NPD3059 Approved
0.7055 Intermediate Similarity NPD3061 Approved
0.7048 Intermediate Similarity NPD7472 Approved
0.7047 Intermediate Similarity NPD3539 Phase 1
0.7047 Intermediate Similarity NPD2438 Suspended
0.7045 Intermediate Similarity NPD5451 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