Natural Product: NPC98179

Natural Product IDNPC98179
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Marmesin
IUPAC Name (2S)-2-(2-hydroxypropan-2-yl)-2,3-dihydrofuro[3,2-g]chromen-7-one
Synonyms Marmesin
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL442813
PubChem CID 334704
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives
        • [CHEMONTID:0000358] Furanocoumarins
          • [CHEMONTID:0002569] Linear furanocoumarins
            • [CHEMONTID:0000202] Psoralens

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 FWYSBEAFFPBAQU-LBPRGKRZSA-N
Standard InCHI InChI=1S/C14H14O4/c1-14(2,16)12-6-9-5-8-3-4-13(15)18-10(8)7-11(9)17-12/h3-5,7,12,16H,6H2,1-2H3/t12-/m0/s1
SMILES CC(C)([C@@H]1Cc2cc3ccc(=O)oc3cc2O1)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   246.09 Volume:   247.009
?
Van der Waals volume.
Dense:   0.996 LogP:   2.587
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.425
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.22
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   1.0 Rigid Bonds:   16.0
TPSA:   59.67
?
Topological Polar Surface Area.
 H-Bond Acceptor:   4.0
H-Bond Donor:   1.0 Rings:   3.0
Heavy Atoms:   4.0

MedChem Properties

QED Drug-Likeness Score:   0.78 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.173 Fsp3:   0.357
MCE-18:   57.789
?
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:   Rejected
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.51 Fluc inhibitor:   0.878
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.993
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.185
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.338 Promiscuous compounds:   0.385

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.549 MDCK Permeability:   -4.493
Pgp-inhibitor:   0.037 Pgp-substrate:   0.0
PAMPA:   0.345
?
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):   0.001
20% Bioavailability (F20%):   0.683 30% Bioavailability (F30%):   0.6
50% Bioavailability (F50%):   0.268

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.0 MRP1:   0.999
Plasma Protein Binding (PPB):   72.355% Volume Distribution (VD):   -0.244
Fu: 23.836%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.999
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.0
BSEP inhibitor:   0.999

ADMET: Metabolism

CYP1A2-inhibitor:   0.926 CYP1A2-substrate:   0.024
CYP2C19-inhibitor:   0.928 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.987 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.549 CYP2D6-substrate:   0.324
CYP3A4-inhibitor:   0.597 CYP3A4-substrate:   0.895
CYP2B6-substrate:   0.001 CYP2C8-inhibitor:   0.98
HLM stability:   0.457
?
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):  5.923 Half-life (T1/2):  0.876

ADMET: Toxicity

hERG Blockers:  0.145 hERG Blockers (10um):  0.256
Human Hepatotoxicity (H-HT):  0.608 Drug-induced Liver Injury (DILI):  0.774
AMES Toxicity:  0.702 Rat Oral Acute Toxicity:  0.586
Maximum Recommended Daily Dose:  0.81 Skin Sensitization:  0.501
Carcinogencity:  0.808 Eye Corrosion:  0.076
Eye Irritation:  0.979 Respiratory Toxicity:  0.844
Drug-induced Neurotoxicity:  0.338 Ototoxicity:  0.323
Hematotoxicity:  0.358 Drug-induced Nephrotoxicity:  0.501
Genotoxicity:  0.974 RPMI-8226 Immunitoxicity:  0.066
A549 Cytotoxicity:  0.078 Hek293 Cytotoxicity:  0.274
BCF:   0.595
?
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:   3.268
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.617
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.032
?
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
NPO64852 Mangrove + Fusarium sp. symbiont Species n.a. n.a. n.a. n.a. n.a. PMID[ 21213977]
NPO64794 Moringa oleifera + Nigrospora sp. symbiont Species n.a. n.a. n.a. n.a. n.a. PMID[ 22806033]
NPO64741 Forsythia viridissima + Pezicula sp. symbiont Species n.a. n.a. n.a. n.a. n.a. PMID[ 24928260]
NPO64719 Litsea akoensis + Xylaria cubensis symbiont Species n.a. n.a. n.a. n.a. n.a. DOI[10.1002/hlca.201400091]
NPO64621 Cinnamomum sp. + Annulohypoxylon bovei var. microspora symbiont Species n.a. n.a. n.a. n.a. n.a. DOI[10.1007/s10600-011-9990-5]
NPO64667 Prumnopitys andina + Penicillium janczewskii symbiont Species n.a. n.a. n.a. n.a. n.a. DOI[10.1007/s11274-004-1552-6]
NPO64727 Sapindus saponaria + Xylariaceae sp. symbiont Species n.a. n.a. n.a. n.a. n.a. DOI[10.1007/s11274-007-9607-0]
NPO64633 Cinnamomum sp. + Annulohypoxylon squamulosum symbiont Species n.a. n.a. n.a. n.a. n.a. DOI[10.1016/j.phytol.2011.12.012]
NPO64951 Garcinia sp. + Xylaria sp. symbiont Species n.a. n.a. n.a. n.a. n.a. DOI[10.1016/j.phytol.2012.11.007]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. DOI[10.5012/bkcs.2003.24.11.1699]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[11374978]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. root n.a. PMID[11395279]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota whole plants Shawnee National Forest, Harrisburg, IL, US n.a. PMID[11678652]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota whole plants n.a. n.a. PMID[11678652]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. PMID[12419367]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[12510838]
NPO17729 Tephrosia toxicaria Species Geometridae Eukaryota n.a. stem n.a. PMID[14510590]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[1453177]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[15646793]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15679317]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota roots purchased from Kiu Shun Trading Ltd., Vancouver, Canada 2000 PMID[16643021]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[17703773]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[17997069]
NPO5045 Aegle marmelos Species Rutaceae Eukaryota leaves n.a. n.a. PMID[18760601]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota leaves Kaohsiung, Taiwan 2006-SEP PMID[18986201]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota Fruits n.a. n.a. PMID[19296617]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota rhizomes n.a. n.a. PMID[19757853]
NPO8369 Antiaris toxicaria Species Moraceae Eukaryota n.a. n.a. n.a. PMID[20553004]
NPO30526 Notopterygium incisum n.a. n.a. n.a. n.a. root n.a. PMID[20707067]
NPO30526 Notopterygium incisum n.a. n.a. n.a. n.a. rhizome n.a. PMID[20707067]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota n.a. rhizome n.a. PMID[21370894]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[21657081]
NPO5045 Aegle marmelos Species Rutaceae Eukaryota n.a. bark n.a. PMID[21875114]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. root n.a. PMID[22784551]
NPO5045 Aegle marmelos Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[23434131]
NPO8369 Antiaris toxicaria Species Moraceae Eukaryota latex Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Yunnan Province, China 2011-Mar PMID[24033101]
NPO8369 Antiaris toxicaria Species Moraceae Eukaryota trunk bark Yunnan, China n.a. PMID[24582402]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[24813739]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. root n.a. PMID[25068578]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25333853]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25538068]
NPO5045 Aegle marmelos Species Rutaceae Eukaryota n.a. fruit n.a. PMID[26247834]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27400088]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27444348]
NPO5045 Aegle marmelos Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[30579794]
NPO5045 Aegle marmelos Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[31302251]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota Roots n.a. n.a. PMID[31464439]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[36838931]
NPO30526 Notopterygium incisum n.a. n.a. n.a. n.a. n.a. n.a. PMID[37382684]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[37480748]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[38830452]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota Rhizomes n.a. n.a. PMID[8482946]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. formosan n.a. PMID[8864236]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. PMID[9358644]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO854 Fucus serratus Species Fucaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17729 Tephrosia toxicaria Species Geometridae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7279 Ferulago capillaries Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12746 Pleurospermum rivulorum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16614 Zanthoxylum spinosum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO30526 Notopterygium incisum n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO5045 Aegle marmelos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2629 Cystoseira caespitosa Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1117 Hypholoma capnoides Species Strophariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24248.1 Lactarius deliciosus var. deterrimus Varieties Russulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9366 Rosa transmorrisonensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4812 Cynometra hankei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8369 Antiaris toxicaria Species Moraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28975 Thamnosma rhodesica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23235 Zanthoxylum arnottianum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30526 Notopterygium incisum n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12746 Pleurospermum rivulorum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24205 Peucedanum terebinthaceum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7279 Ferulago capillaries Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17866 Peucedanum rubricaule Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25702 Angelica pachycarpa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8369 Antiaris toxicaria Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17729 Tephrosia toxicaria Species Geometridae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2655 Heracleum rapula Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5045 Aegle marmelos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28975 Thamnosma rhodesica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12746 Pleurospermum rivulorum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17729 Tephrosia toxicaria Species Geometridae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11302 Hymenidium lindleyanum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17866 Peucedanum rubricaule Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25702 Angelica pachycarpa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8369 Antiaris toxicaria Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2655 Heracleum rapula Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24205 Peucedanum terebinthaceum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7279 Ferulago capillaries Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23235 Zanthoxylum arnottianum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5045 Aegle marmelos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17866 Peucedanum rubricaule Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5045 Aegle marmelos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30526 Notopterygium incisum n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2629 Cystoseira caespitosa Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4812 Cynometra hankei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9366 Rosa transmorrisonensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24248.1 Lactarius deliciosus var. deterrimus Varieties Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1538 Lepechinia hastata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16614 Zanthoxylum spinosum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1117 Hypholoma capnoides Species Strophariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24079 Eucalyptus laevopinea Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1100 Croton joufra Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6128 Hunteria eburnea Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28975 Thamnosma rhodesica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3750 Solidago missouriensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23235 Zanthoxylum arnottianum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8067 Pelargonium crispum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8369 Antiaris toxicaria Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7614 Laurus camphora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO854 Fucus serratus Species Fucaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25702 Angelica pachycarpa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17729 Tephrosia toxicaria Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24205 Peucedanum terebinthaceum Species Apiaceae 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
NPO16755 Saposhnikovia divaricata n.a. Roots 229.08586, 213.05461, 175.03899, 119.04936 n.a. n.a. % PMID[38830452]
NPO16755 Saposhnikovia divaricata n.a. Roots 0.16 n.a. n.a. % PMID[38830452]
NPO16755 Saposhnikovia divaricata n.a. Roots 0.08 n.a. n.a. % PMID[38830452]

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
NPT204 Individual protein Acetylcholinesterase Homo sapiens IC50 = 67000.0 nM PMID[11374978]
NPT72 Individual protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 103.86 % PMID[23571415]
NPT740 Individual protein Beta-secretase 1 Homo sapiens IC50 > 500000.0 nM PMID[22222157]
NPT740 Individual protein Beta-secretase 1 Homo sapiens Inhibition = 2.9 % PMID[22222157]
NPT73 Individual protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 89.64 % PMID[23571415]
NPT441 Individual protein Cytochrome P450 19A1 Homo sapiens IC50 > 40.0 ug.mL-1 PMID[11678652]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell line MCF7 Homo sapiens ED50 > 20.0 ug ml-1 PMID[24582402]
NPT81 Cell line A549 Homo sapiens ED50 > 20.0 ug ml-1 PMID[24582402]

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 NPC98179 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
1.0 High Similarity NPC253574
0.7308 Intermediate Similarity NPC234109
0.7308 Intermediate Similarity NPC188327
0.6491 Remote Similarity NPC235682
0.6491 Remote Similarity NPC608821
0.6364 Remote Similarity NPC33986
0.625 Remote Similarity NPC78746
0.5938 Remote Similarity NPC7526
0.5938 Remote Similarity NPC222036
0.5938 Remote Similarity NPC14248
0.5893 Remote Similarity NPC248429
0.5893 Remote Similarity NPC111347
0.5797 Remote Similarity NPC296377
0.5789 Remote Similarity NPC72281
0.569 Remote Similarity NPC601133
0.5625 Remote Similarity NPC119640
0.5625 Remote Similarity NPC183646
0.5588 Remote Similarity NPC211110
0.5556 Remote Similarity NPC605579
0.5507 Remote Similarity NPC279573
0.5455 Remote Similarity NPC207002
0.5455 Remote Similarity NPC133956
0.5455 Remote Similarity NPC47163
0.5424 Remote Similarity NPC608534
0.5397 Remote Similarity NPC220582
0.5397 Remote Similarity NPC304839
0.5333 Remote Similarity NPC204353
0.5333 Remote Similarity NPC76753
0.5286 Remote Similarity NPC85624
0.5147 Remote Similarity NPC151946
0.5072 Remote Similarity NPC120220

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC98179 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