Structure

Physi-Chem Properties

Molecular Weight:  426.39
Volume:  490.807
LogP:  7.651
LogD:  5.86
LogS:  -6.645
# Rotatable Bonds:  5
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.441
Synthetic Accessibility Score:  5.579
Fsp3:  0.933
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.887
MDCK Permeability:  1.1121113857370801e-05
Pgp-inhibitor:  0.156
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.989
30% Bioavailability (F30%):  0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.143
Plasma Protein Binding (PPB):  94.38288116455078%
Volume Distribution (VD):  1.314
Pgp-substrate:  1.890112280845642%

ADMET: Metabolism

CYP1A2-inhibitor:  0.061
CYP1A2-substrate:  0.422
CYP2C19-inhibitor:  0.08
CYP2C19-substrate:  0.959
CYP2C9-inhibitor:  0.188
CYP2C9-substrate:  0.212
CYP2D6-inhibitor:  0.143
CYP2D6-substrate:  0.563
CYP3A4-inhibitor:  0.931
CYP3A4-substrate:  0.858

ADMET: Excretion

Clearance (CL):  9.592
Half-life (T1/2):  0.036

ADMET: Toxicity

hERG Blockers:  0.949
Human Hepatotoxicity (H-HT):  0.176
Drug-inuced Liver Injury (DILI):  0.805
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.147
Maximum Recommended Daily Dose:  0.042
Skin Sensitization:  0.932
Carcinogencity:  0.311
Eye Corrosion:  0.454
Eye Irritation:  0.121
Respiratory Toxicity:  0.838

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  Natural Product: NPC49168

Natural Product ID:  NPC49168
Common Name*:   Cycloeucalenol
IUPAC Name:   n.a.
Synonyms:   Cycloeucalenol
Standard InCHIKey:  HUNLTIZKNQDZEI-PGFZVWMDSA-N
Standard InCHI:  InChI=1S/C30H50O/c1-19(2)20(3)8-9-21(4)23-12-14-28(7)26-11-10-24-22(5)25(31)13-15-29(24)18-30(26,29)17-16-27(23,28)6/h19,21-26,31H,3,8-18H2,1-2,4-7H3/t21-,22+,23-,24+,25+,26+,27-,28+,29-,30+/m1/s1
SMILES:  CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4[C@H](C)[C@H](CC[C@]54C[C@@]35CC[C@]12C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL225634
PubChem CID:   101690
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO26629 Caesalpinia pulcherrima Species Fabaceae Eukaryota n.a. stem n.a. DOI[10.1021/np0201523]
NPO24176 Streptomyces fradiae Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10757717]
NPO23281 Aplysinella rhax Species Aplysinellidae Eukaryota n.a. n.a. n.a. PMID[10757728]
NPO24219 Erylus nobilis Species n.a. n.a. n.a. n.a. n.a. PMID[11421740]
NPO24219 Erylus nobilis Species n.a. n.a. n.a. n.a. n.a. PMID[11908993]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[11914965]
NPO17048 Jungermannia subulata Species Jungermanniaceae Eukaryota n.a. n.a. n.a. PMID[11999396]
NPO26629 Caesalpinia pulcherrima Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[12193012]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[12350165]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. Okinawan, Japan n.a. PMID[14695804]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[15332859]
NPO15538 Eucalyptus citriodora Species Myrtaceae Eukaryota Leaves the campus of Panjab University, Chandigarh, India PMID[16989303]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[17407351]
NPO23281 Aplysinella rhax Species Aplysinellidae Eukaryota n.a. n.a. n.a. PMID[17827010]
NPO20637 Piper acutifolium Species Piperaceae Eukaryota n.a. leaf n.a. PMID[18712933]
NPO26661 Heimia salicifolia Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. PMID[20488581]
NPO23499 Carpesium faberi Species Asteraceae Eukaryota whole plant Changshou County, Chongqing, China 2008-Aug PMID[21109433]
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota n.a. root n.a. PMID[22779710]
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[22779710]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota Roots n.a. n.a. PMID[24054487]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota roots n.a. n.a. PMID[24412339]
NPO15538 Eucalyptus citriodora Species Myrtaceae Eukaryota Essential oil n.a. n.a. PMID[24641242]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[25987373]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[27116034]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[28294615]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[29667821]
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota Roots n.a. n.a. PMID[31625742]
NPO26629 Caesalpinia pulcherrima Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[3783154]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[7807132]
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO14246 Helleborus thibetanus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22455 Corydalis sewerzowi Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21625 Bidens tripartita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16027 Niphogeton ternata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26629 Caesalpinia pulcherrima Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14650 Lobelia chinensis Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18366 Papaver commutatum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO21625 Bidens tripartita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18366 Papaver commutatum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22455 Corydalis sewerzowi Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16027 Niphogeton ternata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15538 Eucalyptus citriodora Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14650 Lobelia chinensis Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26172 Dryopteris sacrosancta Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15580 Justicia simplex Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26629 Caesalpinia pulcherrima Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14246 Helleborus thibetanus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18366 Papaver commutatum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14650 Lobelia chinensis Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15580 Justicia simplex Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24090 Aplysilla rosea Species Darwinellidae Eukaryota n.a. Austrila n.a. Database[Title]
NPO14650 Lobelia chinensis Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15538 Eucalyptus citriodora Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8534 Cineraria saxifraga Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26906 Astragalus interpositus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23961 Scytonema ocellatum Species Scytonemataceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26383 Lemna trisulca Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24219 Erylus nobilis Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO23834 Chlamydomonas allensworthii Species Chlamydomonadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21295 Botryotrichum piluliferum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16043 Centaurea musimomum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22143 Genista sessilifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20637 Piper acutifolium Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26190 Aspergillus wentii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21625 Bidens tripartita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23545 Vellozia streptophylla Species Velloziaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7166 Streptomyces aureus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18566 Gymnocladus dioicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26629 Caesalpinia pulcherrima Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13645 Armoracia rusticana Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13127 Vallaris heynei Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25876 Chromodoris inornata Species Chromodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26411 Stemphylium radicinum Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24445 Arbacia pustulosa Species Arbaciidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15580 Justicia simplex Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17264 Mycena haematopus Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24176 Streptomyces fradiae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO15416 Petasites fragrans Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23364 Lambertella corni Species Rutstroemiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8593 Zygosaccharomyces rouxii Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12429 Acicarpha tribuloides Species Calyceraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29041 Scutellaria orientalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15832 Ruscus hypophyllum Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23281 Aplysinella rhax Species Aplysinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17737 Lepidorhinus squamosus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO24132 Euphausia superba Species Euphausiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24249 Codonopsis cordifolioidea Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26215 Eleusine indica Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23211 Xyris indica Species Xyridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO738 Dahlstedtia pentaphylla Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13892 Calea clausseniana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO426 Camellia reticulata Species Theaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18434 Dactylosporangium aurantiacum Species Micromonosporaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18976 Centaurea arbutifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26433 Conus marmoreus Species Conidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16421 Chalciporus piperatus Species Boletaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17933 Cylicodaphne sebifera n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26839 Microlepia speluncae Species Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17048 Jungermannia subulata Species Jungermanniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21665.1 Mycobacterium avium subsp. paratuberculosis Subspecies Mycobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24005 Mytilus galloprovincialis Species Mytilidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26888 Narcissus asturiensis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22455 Corydalis sewerzowi Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16942 Asparagus thunbergianus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23459 Onoseris alata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23413 Crematogaster africana Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2066 Streptomyces ipomoeae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16631 Libocedrus yateensis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14650 Lobelia chinensis Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4283 Tripteris vaillantii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18366 Papaver commutatum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11999 Piptadenia peregrina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20998 Machaerium kuhlmannii Species Dolichopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17488 Rhoiptelea chiliantha Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17168 Ageratina riparia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16027 Niphogeton ternata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14246 Helleborus thibetanus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18903 Chromodoris willani Species Chromodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23499 Carpesium faberi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24090 Aplysilla rosea Species Darwinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23318 Aconitum palmatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21827 Albatrellus caeruleoporus Species Albatrellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22595 Trapa bicornis Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23696 Solanum diflorum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26931 Dolichothele uberiformis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO23739 Staehelina fruticosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23043 Cryptolestes pusillus Species Laemophloeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23884 Hippobroma longiflora Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23920 Amanita pseudoporphyria Species Amanitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23114 Cacalia robusta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22324 Erium villosum Species Pseudococcidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23610 Aconitum tianschanicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26172 Dryopteris sacrosancta Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24290 Claviceps microcephala Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5782 Aniba rosaeodora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23792 Gomphostemma parviflorum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26661 Heimia salicifolia Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24048 Cladonia pityrea Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24408 Ariocarpus fissuratus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19535 Senecio zoellneri Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26568 Rubus koehneanus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18044 Lotus albus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5062 Aristolochia tagala Species Aristolochiaceae 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
NPT80 Cell Line Raji Homo sapiens Activity = 70.0 % PMID[533093]
NPT164 Organism Human herpesvirus 4 Human herpesvirus 4 Inhibition = 0.0 % PMID[533093]
NPT164 Organism Human herpesvirus 4 Human herpesvirus 4 Inhibition = 26.5 % PMID[533093]
NPT164 Organism Human herpesvirus 4 Human herpesvirus 4 Inhibition = 68.1 % PMID[533093]
NPT164 Organism Human herpesvirus 4 Human herpesvirus 4 Inhibition = 94.8 % PMID[533093]
NPT164 Organism Human herpesvirus 4 Human herpesvirus 4 IC50 = 8.9 nM PMID[533093]
NPT2 Others Unspecified Activity = 1.7 n.a. PMID[533093]

☑ 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 NPC49168 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 NPC145552
1.0 High Similarity NPC5046
1.0 High Similarity NPC254509
1.0 High Similarity NPC196358
0.9855 High Similarity NPC70982
0.9855 High Similarity NPC230704
0.9855 High Similarity NPC200243
0.9853 High Similarity NPC195489
0.9706 High Similarity NPC111234
0.9577 High Similarity NPC331618
0.9577 High Similarity NPC257191
0.9559 High Similarity NPC45296
0.9444 High Similarity NPC472342
0.9444 High Similarity NPC65897
0.9444 High Similarity NPC85346
0.9444 High Similarity NPC302041
0.9429 High Similarity NPC62657
0.9429 High Similarity NPC192638
0.9429 High Similarity NPC25511
0.9296 High Similarity NPC240235
0.9296 High Similarity NPC3403
0.9296 High Similarity NPC178383
0.9296 High Similarity NPC212879
0.9296 High Similarity NPC104387
0.9296 High Similarity NPC185536
0.9296 High Similarity NPC231256
0.9178 High Similarity NPC312328
0.9167 High Similarity NPC93662
0.9167 High Similarity NPC14112
0.9167 High Similarity NPC86305
0.9167 High Similarity NPC78067
0.9167 High Similarity NPC237460
0.9167 High Similarity NPC278091
0.9167 High Similarity NPC91573
0.9155 High Similarity NPC472503
0.9155 High Similarity NPC308440
0.9041 High Similarity NPC202540
0.9041 High Similarity NPC119355
0.9041 High Similarity NPC248830
0.9041 High Similarity NPC212241
0.8919 High Similarity NPC285761
0.8919 High Similarity NPC102708
0.8919 High Similarity NPC6978
0.8919 High Similarity NPC167037
0.8919 High Similarity NPC244385
0.8919 High Similarity NPC31828
0.8919 High Similarity NPC477819
0.8919 High Similarity NPC138621
0.8919 High Similarity NPC42853
0.8919 High Similarity NPC477817
0.8919 High Similarity NPC301707
0.8904 High Similarity NPC189883
0.8831 High Similarity NPC113978
0.8824 High Similarity NPC41577
0.8824 High Similarity NPC473276
0.8824 High Similarity NPC476737
0.8824 High Similarity NPC474380
0.8824 High Similarity NPC27243
0.88 High Similarity NPC49599
0.88 High Similarity NPC80297
0.88 High Similarity NPC116119
0.88 High Similarity NPC475727
0.88 High Similarity NPC472742
0.88 High Similarity NPC273410
0.88 High Similarity NPC80530
0.88 High Similarity NPC49627
0.8784 High Similarity NPC34019
0.8784 High Similarity NPC260301
0.8784 High Similarity NPC307336
0.8784 High Similarity NPC138502
0.8767 High Similarity NPC257347
0.8767 High Similarity NPC121744
0.8767 High Similarity NPC322353
0.8767 High Similarity NPC103822
0.8767 High Similarity NPC141071
0.8767 High Similarity NPC118508
0.8767 High Similarity NPC471723
0.8684 High Similarity NPC102253
0.8684 High Similarity NPC78545
0.8684 High Similarity NPC13554
0.8684 High Similarity NPC71535
0.8684 High Similarity NPC475679
0.8684 High Similarity NPC322313
0.8684 High Similarity NPC236237
0.8676 High Similarity NPC69149
0.8667 High Similarity NPC472499
0.8667 High Similarity NPC472500
0.8667 High Similarity NPC472501
0.8649 High Similarity NPC73875
0.8649 High Similarity NPC134330
0.8649 High Similarity NPC38141
0.8649 High Similarity NPC46160
0.8649 High Similarity NPC129165
0.8649 High Similarity NPC202642
0.8649 High Similarity NPC300324
0.8649 High Similarity NPC240604
0.863 High Similarity NPC476736
0.8611 High Similarity NPC164045
0.8611 High Similarity NPC301226
0.8608 High Similarity NPC76518
0.859 High Similarity NPC82623
0.859 High Similarity NPC134481
0.8571 High Similarity NPC473230
0.8571 High Similarity NPC475884
0.8553 High Similarity NPC1319
0.8553 High Similarity NPC24504
0.8553 High Similarity NPC476316
0.8533 High Similarity NPC214570
0.8514 High Similarity NPC136188
0.8514 High Similarity NPC22105
0.8514 High Similarity NPC230301
0.8514 High Similarity NPC285893
0.8514 High Similarity NPC162742
0.8514 High Similarity NPC288035
0.8514 High Similarity NPC304309
0.8514 High Similarity NPC134847
0.8514 High Similarity NPC28657
0.85 High Similarity NPC71520
0.85 High Similarity NPC269058
0.8493 Intermediate Similarity NPC201373
0.8493 Intermediate Similarity NPC472506
0.8493 Intermediate Similarity NPC211009
0.8481 Intermediate Similarity NPC86238
0.8462 Intermediate Similarity NPC296701
0.8462 Intermediate Similarity NPC477599
0.8462 Intermediate Similarity NPC218616
0.8442 Intermediate Similarity NPC47149
0.8442 Intermediate Similarity NPC236112
0.8442 Intermediate Similarity NPC206735
0.8421 Intermediate Similarity NPC475
0.8421 Intermediate Similarity NPC275910
0.8421 Intermediate Similarity NPC205455
0.8421 Intermediate Similarity NPC186191
0.8421 Intermediate Similarity NPC472502
0.84 Intermediate Similarity NPC113733
0.84 Intermediate Similarity NPC321016
0.84 Intermediate Similarity NPC321381
0.84 Intermediate Similarity NPC107059
0.84 Intermediate Similarity NPC470362
0.8395 Intermediate Similarity NPC89747
0.8382 Intermediate Similarity NPC71460
0.8382 Intermediate Similarity NPC148174
0.8382 Intermediate Similarity NPC218585
0.8378 Intermediate Similarity NPC100334
0.8378 Intermediate Similarity NPC469534
0.8378 Intermediate Similarity NPC469533
0.8378 Intermediate Similarity NPC469593
0.8375 Intermediate Similarity NPC22133
0.8354 Intermediate Similarity NPC207013
0.8354 Intermediate Similarity NPC470929
0.8354 Intermediate Similarity NPC475726
0.8354 Intermediate Similarity NPC5280
0.8354 Intermediate Similarity NPC110778
0.8354 Intermediate Similarity NPC232023
0.8354 Intermediate Similarity NPC216420
0.8354 Intermediate Similarity NPC85095
0.8354 Intermediate Similarity NPC211135
0.8354 Intermediate Similarity NPC477818
0.8354 Intermediate Similarity NPC246956
0.8354 Intermediate Similarity NPC472743
0.8333 Intermediate Similarity NPC241085
0.8333 Intermediate Similarity NPC157655
0.8333 Intermediate Similarity NPC474531
0.8333 Intermediate Similarity NPC210323
0.8333 Intermediate Similarity NPC299948
0.8333 Intermediate Similarity NPC470830
0.8312 Intermediate Similarity NPC30986
0.8312 Intermediate Similarity NPC209430
0.8312 Intermediate Similarity NPC472463
0.8312 Intermediate Similarity NPC5604
0.8312 Intermediate Similarity NPC47808
0.8293 Intermediate Similarity NPC67872
0.8293 Intermediate Similarity NPC146937
0.8289 Intermediate Similarity NPC198968
0.8289 Intermediate Similarity NPC155986
0.8289 Intermediate Similarity NPC318495
0.8272 Intermediate Similarity NPC94462
0.8267 Intermediate Similarity NPC144075
0.8261 Intermediate Similarity NPC114891
0.825 Intermediate Similarity NPC74595
0.825 Intermediate Similarity NPC474482
0.825 Intermediate Similarity NPC264665
0.825 Intermediate Similarity NPC255882
0.825 Intermediate Similarity NPC475745
0.825 Intermediate Similarity NPC209802
0.8243 Intermediate Similarity NPC182717
0.8228 Intermediate Similarity NPC470049
0.8228 Intermediate Similarity NPC472504
0.8228 Intermediate Similarity NPC30166
0.8228 Intermediate Similarity NPC477858
0.8228 Intermediate Similarity NPC248886
0.8194 Intermediate Similarity NPC2648
0.8194 Intermediate Similarity NPC160209
0.8182 Intermediate Similarity NPC477522
0.8182 Intermediate Similarity NPC473943
0.8182 Intermediate Similarity NPC18603
0.8182 Intermediate Similarity NPC474216
0.8182 Intermediate Similarity NPC76931
0.8182 Intermediate Similarity NPC87604
0.8182 Intermediate Similarity NPC307965

  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 NPC49168 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
0.8684 High Similarity NPD7525 Registered
0.8514 High Similarity NPD7339 Approved
0.8514 High Similarity NPD6942 Approved
0.8148 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7922 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7848 Intermediate Similarity NPD7645 Phase 2
0.7838 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD6924 Approved
0.7662 Intermediate Similarity NPD6926 Approved
0.7632 Intermediate Similarity NPD7151 Approved
0.7632 Intermediate Similarity NPD7152 Approved
0.7632 Intermediate Similarity NPD7150 Approved
0.7632 Intermediate Similarity NPD4243 Approved
0.76 Intermediate Similarity NPD6922 Approved
0.76 Intermediate Similarity NPD6923 Approved
0.759 Intermediate Similarity NPD4786 Approved
0.7558 Intermediate Similarity NPD5328 Approved
0.75 Intermediate Similarity NPD4787 Phase 1
0.75 Intermediate Similarity NPD7144 Approved
0.75 Intermediate Similarity NPD7143 Approved
0.747 Intermediate Similarity NPD4788 Approved
0.7468 Intermediate Similarity NPD6933 Approved
0.7436 Intermediate Similarity NPD4785 Approved
0.7436 Intermediate Similarity NPD4784 Approved
0.7412 Intermediate Similarity NPD3618 Phase 1
0.7403 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD8035 Phase 2
0.7386 Intermediate Similarity NPD8034 Phase 2
0.7386 Intermediate Similarity NPD6079 Approved
0.7349 Intermediate Similarity NPD3667 Approved
0.7317 Intermediate Similarity NPD4748 Discontinued
0.725 Intermediate Similarity NPD6117 Approved
0.7215 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD6929 Approved
0.716 Intermediate Similarity NPD6116 Phase 1
0.7143 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD4190 Phase 3
0.7125 Intermediate Similarity NPD5275 Approved
0.7111 Intermediate Similarity NPD4202 Approved
0.7108 Intermediate Similarity NPD6930 Phase 2
0.7108 Intermediate Similarity NPD6931 Approved
0.7108 Intermediate Similarity NPD7509 Discontinued
0.7073 Intermediate Similarity NPD6118 Approved
0.7073 Intermediate Similarity NPD6114 Approved
0.7073 Intermediate Similarity NPD6697 Approved
0.7073 Intermediate Similarity NPD6115 Approved
0.7024 Intermediate Similarity NPD6902 Approved
0.6977 Remote Similarity NPD3665 Phase 1
0.6977 Remote Similarity NPD3666 Approved
0.6977 Remote Similarity NPD3133 Approved
0.6951 Remote Similarity NPD6925 Approved
0.6951 Remote Similarity NPD6932 Approved
0.6951 Remote Similarity NPD5776 Phase 2
0.6915 Remote Similarity NPD7638 Approved
0.6914 Remote Similarity NPD3703 Phase 2
0.6882 Remote Similarity NPD4697 Phase 3
0.6882 Remote Similarity NPD5222 Approved
0.6882 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6882 Remote Similarity NPD5221 Approved
0.6867 Remote Similarity NPD7145 Approved
0.686 Remote Similarity NPD6695 Phase 3
0.6842 Remote Similarity NPD7640 Approved
0.6842 Remote Similarity NPD7639 Approved
0.6835 Remote Similarity NPD4245 Approved
0.6835 Remote Similarity NPD4244 Approved
0.6835 Remote Similarity NPD4789 Approved
0.6813 Remote Similarity NPD7515 Phase 2
0.6809 Remote Similarity NPD4755 Approved
0.6809 Remote Similarity NPD5173 Approved
0.6795 Remote Similarity NPD5360 Phase 3
0.6795 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6786 Remote Similarity NPD4195 Approved
0.6786 Remote Similarity NPD6683 Phase 2
0.6782 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6739 Remote Similarity NPD6399 Phase 3
0.6709 Remote Similarity NPD3698 Phase 2
0.6706 Remote Similarity NPD6928 Phase 2
0.6706 Remote Similarity NPD7514 Phase 3
0.6705 Remote Similarity NPD6893 Approved
0.6667 Remote Similarity NPD4700 Approved
0.6667 Remote Similarity NPD4696 Approved
0.6667 Remote Similarity NPD5285 Approved
0.6667 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5286 Approved
0.6629 Remote Similarity NPD5279 Phase 3
0.6623 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6598 Remote Similarity NPD5223 Approved
0.6593 Remote Similarity NPD4753 Phase 2
0.6591 Remote Similarity NPD3668 Phase 3
0.6562 Remote Similarity NPD5290 Discontinued
0.6556 Remote Similarity NPD7524 Approved
0.6556 Remote Similarity NPD7750 Discontinued
0.6552 Remote Similarity NPD4221 Approved
0.6552 Remote Similarity NPD4223 Phase 3
0.6531 Remote Similarity NPD5224 Approved
0.6531 Remote Similarity NPD5226 Approved
0.6531 Remote Similarity NPD5225 Approved
0.6531 Remote Similarity NPD4633 Approved
0.6531 Remote Similarity NPD5211 Phase 2
0.6517 Remote Similarity NPD5329 Approved
0.6512 Remote Similarity NPD7332 Phase 2
0.6506 Remote Similarity NPD8264 Approved
0.65 Remote Similarity NPD5739 Approved
0.65 Remote Similarity NPD6402 Approved
0.65 Remote Similarity NPD7128 Approved
0.65 Remote Similarity NPD6675 Approved
0.6489 Remote Similarity NPD7748 Approved
0.6471 Remote Similarity NPD3671 Phase 1
0.6465 Remote Similarity NPD5175 Approved
0.6465 Remote Similarity NPD4754 Approved
0.6465 Remote Similarity NPD5174 Approved
0.6437 Remote Similarity NPD6898 Phase 1
0.6404 Remote Similarity NPD4197 Approved
0.64 Remote Similarity NPD5141 Approved
0.6375 Remote Similarity NPD6705 Phase 1
0.6373 Remote Similarity NPD6899 Approved
0.6373 Remote Similarity NPD7320 Approved
0.6373 Remote Similarity NPD6881 Approved
0.6364 Remote Similarity NPD7632 Discontinued
0.6341 Remote Similarity NPD4758 Discontinued
0.6337 Remote Similarity NPD4768 Approved
0.6337 Remote Similarity NPD4767 Approved
0.6324 Remote Similarity NPD384 Approved
0.6324 Remote Similarity NPD385 Approved
0.6311 Remote Similarity NPD6372 Approved
0.6311 Remote Similarity NPD6373 Approved
0.6304 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6289 Remote Similarity NPD7902 Approved
0.6289 Remote Similarity NPD6084 Phase 2
0.6289 Remote Similarity NPD6083 Phase 2
0.6279 Remote Similarity NPD3617 Approved
0.6277 Remote Similarity NPD7087 Discontinued
0.6275 Remote Similarity NPD5701 Approved
0.6275 Remote Similarity NPD5697 Approved
0.6264 Remote Similarity NPD4690 Approved
0.6264 Remote Similarity NPD7146 Approved
0.6264 Remote Similarity NPD4138 Approved
0.6264 Remote Similarity NPD5330 Approved
0.6264 Remote Similarity NPD4688 Approved
0.6264 Remote Similarity NPD7521 Approved
0.6264 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6264 Remote Similarity NPD4693 Phase 3
0.6264 Remote Similarity NPD7334 Approved
0.6264 Remote Similarity NPD6684 Approved
0.6264 Remote Similarity NPD4689 Approved
0.6264 Remote Similarity NPD6409 Approved
0.6264 Remote Similarity NPD5205 Approved
0.6263 Remote Similarity NPD4159 Approved
0.625 Remote Similarity NPD7102 Approved
0.625 Remote Similarity NPD5210 Approved
0.625 Remote Similarity NPD7290 Approved
0.625 Remote Similarity NPD6356 Clinical (unspecified phase)
0.625 Remote Similarity NPD6883 Approved
0.625 Remote Similarity NPD4629 Approved
0.6237 Remote Similarity NPD6051 Approved
0.6214 Remote Similarity NPD5168 Approved
0.6214 Remote Similarity NPD4730 Approved
0.6214 Remote Similarity NPD6011 Approved
0.6214 Remote Similarity NPD4729 Approved
0.6214 Remote Similarity NPD5128 Approved
0.619 Remote Similarity NPD6650 Approved
0.619 Remote Similarity NPD6847 Approved
0.619 Remote Similarity NPD8130 Phase 1
0.619 Remote Similarity NPD6869 Approved
0.619 Remote Similarity NPD6617 Approved
0.619 Remote Similarity NPD6401 Clinical (unspecified phase)
0.619 Remote Similarity NPD6649 Approved
0.617 Remote Similarity NPD6701 Clinical (unspecified phase)
0.617 Remote Similarity NPD6700 Approved
0.6154 Remote Similarity NPD6012 Approved
0.6154 Remote Similarity NPD6013 Approved
0.6154 Remote Similarity NPD6014 Approved
0.6145 Remote Similarity NPD6081 Approved
0.6132 Remote Similarity NPD8297 Approved
0.6132 Remote Similarity NPD6882 Approved
0.6129 Remote Similarity NPD6903 Approved
0.6129 Remote Similarity NPD4722 Approved
0.6129 Remote Similarity NPD4723 Approved
0.6129 Remote Similarity NPD6672 Approved
0.6129 Remote Similarity NPD5737 Approved
0.6125 Remote Similarity NPD4224 Phase 2
0.6105 Remote Similarity NPD6703 Approved
0.6105 Remote Similarity NPD6702 Approved
0.6095 Remote Similarity NPD5251 Approved
0.6095 Remote Similarity NPD4634 Approved
0.6095 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6095 Remote Similarity NPD5248 Approved
0.6095 Remote Similarity NPD5135 Approved
0.6095 Remote Similarity NPD5249 Phase 3
0.6095 Remote Similarity NPD5169 Approved
0.6095 Remote Similarity NPD5247 Approved
0.6095 Remote Similarity NPD5250 Approved
0.6092 Remote Similarity NPD5364 Discontinued
0.6087 Remote Similarity NPD5690 Phase 2
0.6087 Remote Similarity NPD5280 Approved
0.6087 Remote Similarity NPD4694 Approved
0.6067 Remote Similarity NPD4692 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