Natural Product: NPC133609

Natural Product IDNPC133609
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Notoamide F
IUPAC Name n.a.
Synonyms Notoamide F
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL461207
PubChem CID 25180710
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0001734] Pyrroloquinolines

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

  Chemical Representations

Standard InCHIKey RWPUAUNPEMCSNR-CZQHCSHRSA-N
Standard InCHI InChI=1S/C27H31N3O4/c1-24(2)11-9-14-16(34-24)8-7-15-18-20(28-19(14)15)25(3,4)17-13-26-10-6-12-30(26)23(32)27(17,21(18)33-5)29-22(26)31/h7-9,11,17,21,28H,6,10,12-13H2,1-5H3,(H,29,31)/t17-,21-,26-,27+/m0/s1
SMILES CO[C@H]1c2c3ccc4c(c3[nH]c2C([C@H]2[C@]31N=C(O)[C@@]1(N(C3=O)CCC1)C2)(C)C)C=CC(O4)(C)C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   461.23 Volume:   465.349
?
Van der Waals volume.
Dense:   0.991 LogP:   3.663
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.32
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.466
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   1.0 Rigid Bonds:   33.0
TPSA:   87.15
?
Topological Polar Surface Area.
 H-Bond Acceptor:   7.0
H-Bond Donor:   2.0 Rings:   8.0
Heavy Atoms:   7.0

MedChem Properties

QED Drug-Likeness Score:   0.658 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   6.382 Fsp3:   0.556
MCE-18:   196.952
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Rejected GSK Rule:   Accepted
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.365 Fluc inhibitor:   0.108
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.597
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.778
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.003 Promiscuous compounds:   0.399

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.044 MDCK Permeability:   -4.862
Pgp-inhibitor:   0.367 Pgp-substrate:   0.958
PAMPA:   0.846
?
The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).
 Human Intestinal Absorption (HIA):   0.021
20% Bioavailability (F20%):   0.902 30% Bioavailability (F30%):   0.973
50% Bioavailability (F50%):   0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.035 MRP1:   0.894
Plasma Protein Binding (PPB):   97.152% Volume Distribution (VD):   0.123
Fu: 2.254%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.872
OATP1B3 inhibitor:   0.317 BCRP inhibitor:   0.258
BSEP inhibitor:   0.96

ADMET: Metabolism

CYP1A2-inhibitor:   0.114 CYP1A2-substrate:   0.479
CYP2C19-inhibitor:   0.865 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.458 CYP2C9-substrate:   0.001
CYP2D6-inhibitor:   0.002 CYP2D6-substrate:   0.071
CYP3A4-inhibitor:   0.998 CYP3A4-substrate:   0.652
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.86
HLM stability:   0.945
?
Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):  5.269 Half-life (T1/2):  1.032

ADMET: Toxicity

hERG Blockers:  0.003 hERG Blockers (10um):  0.002
Human Hepatotoxicity (H-HT):  1.0 Drug-induced Liver Injury (DILI):  0.904
AMES Toxicity:  0.977 Rat Oral Acute Toxicity:  0.942
Maximum Recommended Daily Dose:  0.146 Skin Sensitization:  1.0
Carcinogencity:  1.0 Eye Corrosion:  0.0
Eye Irritation:  0.287 Respiratory Toxicity:  0.844
Drug-induced Neurotoxicity:  0.413 Ototoxicity:  0.91
Hematotoxicity:  0.474 Drug-induced Nephrotoxicity:  1.0
Genotoxicity:  1.0 RPMI-8226 Immunitoxicity:  0.003
A549 Cytotoxicity:  0.003 Hek293 Cytotoxicity:  0.103
BCF:   1.498
?
Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].
 IGC50:   4.292
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.695
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   5.224
?
96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO21005 Baphia nitida Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(92)80059-N]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. xylem n.a. DOI[10.1016/S0040-4039(00)86970-1]
NPO4343 Guanomyces polythrix Species n.a. Eukaryota n.a. n.a. n.a. PMID[10869195]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota rhizosphere Sonoran desert n.a. PMID[15620238]
NPO17256 Kobresia nepalensis Species Cyperaceae Eukaryota n.a. stem n.a. PMID[16508191]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[17340534]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17542490]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17564467]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19053517]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21366228]
NPO19192 Sinocalamus affinis Species n.a. n.a. n.a. stem n.a. PMID[21469695]
NPO19192 Sinocalamus affinis Species n.a. n.a. skin-removed stems Pingle Town, Sichuang Province, China 2008-AUG PMID[21469695]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21718031]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21854017]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota healthy leaf of Ginkgo biloba campus of Nanjing University, Nanjing, China 2008-OCT PMID[22196792]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota isolated from the sponge Xestospongia testudinaria n.a. n.a. PMID[22225637]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota Isolated from a sandy-loam soil sample 50 m inland from Waikiki Beach, Honolulu, Hawaii 2010-JUL PMID[22400916]
NPO19192 Sinocalamus affinis Species n.a. n.a. n.a. n.a. n.a. PMID[22690646]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22703109]
NPO19901 Emilia sonchifolia Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[23397723]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23527875]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24050204]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25001296]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25581396]
NPO20739 Jungermannia hyalina Species Jungermanniaceae Eukaryota n.a. Guangxi Zhuang Autonomous Region, China n.a. PMID[25856683]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26273902]
NPO21618 Ircinia oros Species Irciniidae Eukaryota n.a. n.a. n.a. PMID[28840725]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[31012585]
NPO21679 Nuphar lutea Species Nymphaeaceae Eukaryota n.a. n.a. n.a. PMID[31182315]
NPO20212 Callistemon viminalis Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[31276403]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[33305943]
NPO19017 Prangos pabularia Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[35430270]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota Fruits n.a. n.a. PMID[3760884]
NPO20212 Callistemon viminalis Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[38893531]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[6736970]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[6875576]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[6875577]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. xylem n.a. PMID[6875577]
NPO20671 Selliguea feei Species Polypodiaceae Eukaryota Rhizomes n.a. n.a. PMID[8254348]
NPO14136 Acherontia atropus Species Sphingidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21550 Achillea macrophylla Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14330 Agave aurea Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20408 Ajuga spectabilis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21426 Alstroemeria revoluta Species Alstroemeriaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21231 Astragalus tragacantha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21005 Baphia nitida Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20212 Callistemon viminalis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20546 Cissus pallidiflorus Species Vitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19986 Crataegus davisii Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16454 Crinum erubescens Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16044 Cupressus lawsoniana Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19901 Emilia sonchifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15216 Encephalartos altensteinii Species Zamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13260 Eria foetida Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22510 Eupatorium havanense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11966 Euphorbia kamerunica Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19622 Euphorbia marginata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18096 Excoecaria oppositifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20051 Gardenia collinsae Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18620 Grindelia acutifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4343 Guanomyces polythrix Species n.a. Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2854 Gymnosporia senegalensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21618 Ircinia oros Species Irciniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20739 Jungermannia hyalina Species Jungermanniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17256 Kobresia nepalensis Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21365 Ligularia muliensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26840 Litsea aciculata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21088 Litsea pulchella Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21486 Marrubium alysson Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20872 Melampodium heterophyllum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20813 Myrmica sabuleti Species Formicidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3237 Mytilus edulis Species Mytilidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21679 Nuphar lutea Species Nymphaeaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20340 Pausinystalia mayumbensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14466 Penicillium olsonii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16907 Pentzia incana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8650.1 Perilla frutescens var. arguta Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19017 Prangos pabularia Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17515 Pronephrium triphyllum Species Thelypteridaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20671 Selliguea feei Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11622.1 Shuteria involucrata var. vestita Varieties Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19192 Sinocalamus affinis Species n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO3777 Stevia chamaedrys Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21289 Teucrium oxylepis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19488 Trifolium subterraneum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8678 Trillium camschatcense Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20612 Ursinia abrotanifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19773 Xenorhabdus bovienii Species Morganellaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO21679 Nuphar lutea Species Nymphaeaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8650.1 Perilla frutescens var. arguta Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19901 Emilia sonchifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19017 Prangos pabularia Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19488 Trifolium subterraneum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19488 Trifolium subterraneum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19901 Emilia sonchifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8650.1 Perilla frutescens var. arguta Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8678 Trillium camschatcense Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19017 Prangos pabularia Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11966 Euphorbia kamerunica Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17256 Kobresia nepalensis Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21679 Nuphar lutea Species Nymphaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19017 Prangos pabularia Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19901 Emilia sonchifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17256 Kobresia nepalensis Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21231 Astragalus tragacantha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21088 Litsea pulchella Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20813 Myrmica sabuleti Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21679 Nuphar lutea Species Nymphaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11622.1 Shuteria involucrata var. vestita Varieties Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16907 Pentzia incana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14136 Acherontia atropus Species Sphingidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18620 Grindelia acutifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20612 Ursinia abrotanifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19488 Trifolium subterraneum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13260 Eria foetida Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21005 Baphia nitida Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8678 Trillium camschatcense Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14466 Penicillium olsonii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21486 Marrubium alysson Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19622 Euphorbia marginata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20671 Selliguea feei Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21365 Ligularia muliensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3777 Stevia chamaedrys Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19986 Crataegus davisii Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21618 Ircinia oros Species Irciniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4343 Guanomyces polythrix Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16454 Crinum erubescens Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16044 Cupressus lawsoniana Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11966 Euphorbia kamerunica Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19773 Xenorhabdus bovienii Species Morganellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO21550 Achillea macrophylla Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20340 Pausinystalia mayumbensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21426 Alstroemeria revoluta Species Alstroemeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18096 Excoecaria oppositifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26840 Litsea aciculata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19901 Emilia sonchifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19192 Sinocalamus affinis Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO2854 Gymnosporia senegalensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17515 Pronephrium triphyllum Species Thelypteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19017 Prangos pabularia Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3237 Mytilus edulis Species Mytilidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15216 Encephalartos altensteinii Species Zamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14330 Agave aurea Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20739 Jungermannia hyalina Species Jungermanniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20872 Melampodium heterophyllum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22510 Eupatorium havanense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20546 Cissus pallidiflorus Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21289 Teucrium oxylepis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8650.1 Perilla frutescens var. arguta Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20051 Gardenia collinsae Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20212 Callistemon viminalis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20408 Ajuga spectabilis Species Lamiaceae 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 Organism Name 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

Molecular-level activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT165 Cell line HeLa Homo sapiens IC50 > 50.0 ug.mL-1 PMID[19053517]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference





 Experimental ADME

Experiment Model Experiment Tissue ADME Type ADME Relation ADME Value ADME Unit Reference





 Experimental Toxicity

Quantitative toxicity

Experiment Model Experiment Organism Toxicity Type Toxicity Relation Toxicity Value Toxicity Unit Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption
Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]


  Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

●  The left chart: Distribution of similarity level between NPC133609 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score Similarity Level Natural Product ID
0.75 Intermediate Similarity NPC244543
0.7416 Intermediate Similarity NPC131486
0.7174 Intermediate Similarity NPC189079

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC133609 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
NPD

Bioactivity similarity

  Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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