Structure

Physi-Chem Properties

Molecular Weight:  404.13
Volume:  365.702
LogP:  -0.803
LogD:  -1.486
LogS:  -1.12
# Rotatable Bonds:  5
TPSA:  179.28
# H-Bond Aceptor:  11
# H-Bond Donor:  6
# Rings:  3
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.278
Synthetic Accessibility Score:  4.507
Fsp3:  0.706
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.952
MDCK Permeability:  7.893562724348158e-05
Pgp-inhibitor:  0.016
Pgp-substrate:  0.971
Human Intestinal Absorption (HIA):  0.961
20% Bioavailability (F20%):  0.619
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.138
Plasma Protein Binding (PPB):  47.28031539916992%
Volume Distribution (VD):  0.535
Pgp-substrate:  32.13848876953125%

ADMET: Metabolism

CYP1A2-inhibitor:  0.027
CYP1A2-substrate:  0.03
CYP2C19-inhibitor:  0.034
CYP2C19-substrate:  0.104
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.037
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.107
CYP3A4-inhibitor:  0.006
CYP3A4-substrate:  0.016

ADMET: Excretion

Clearance (CL):  1.226
Half-life (T1/2):  0.721

ADMET: Toxicity

hERG Blockers:  0.208
Human Hepatotoxicity (H-HT):  0.075
Drug-inuced Liver Injury (DILI):  0.442
AMES Toxicity:  0.138
Rat Oral Acute Toxicity:  0.372
Maximum Recommended Daily Dose:  0.002
Skin Sensitization:  0.181
Carcinogencity:  0.142
Eye Corrosion:  0.003
Eye Irritation:  0.105
Respiratory Toxicity:  0.185

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

  Natural Product: NPC254848

Natural Product ID:  NPC254848
Common Name*:   RHMXXJGYXNZAPX-UHFFFAOYSA-M
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  RHMXXJGYXNZAPX-UHFFFAOYSA-M
Standard InCHI:  InChI=1S/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3/p-1
SMILES:  Cc1cc2c(c(c1)O)C(=O)c1c(cc(cc1O)[O-])C2=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   25201450
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes
        • [CHEMONTID:0000151] Anthraquinones
          • [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO12955 Rumex crispus Species Polygonaceae Eukaryota n.a. leaf n.a. DOI[10.1002/ardp.19542870405]
NPO15018.1 Dioscorea collettii var. hypoglauca Varieties Dioscoreaceae Eukaryota n.a. n.a. n.a. PMID[10075765]
NPO25430 Xanthoceras sorbifolium Species Sapindaceae Eukaryota n.a. xylem n.a. PMID[10691716]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. seed n.a. PMID[10898633]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[11076555]
NPO23982 Ventilago leiocarpa Species Rhamnaceae Eukaryota n.a. n.a. n.a. PMID[11374975]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota Roots n.a. n.a. PMID[11459643]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota n.a. n.a. n.a. PMID[12081149]
NPO30021 Rheum emodi Species Polygonaceae Eukaryota Roots Gorkha district, Nepal 1996-OCT PMID[12932135]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[1517743]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota n.a. root n.a. PMID[16564530]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota rhizomes n.a. n.a. PMID[19757853]
NPO29334 Oplopanax elatus Species Araliaceae Eukaryota stems n.a. n.a. PMID[20387902]
NPO30179 Cassia occidentalis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21080643]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota n.a. rhizome n.a. PMID[21370894]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota n.a. root n.a. PMID[22051934]
NPO8921 Senna obtusifolia Species Fabaceae Eukaryota Seeds n.a. n.a. PMID[2213033]
NPO31520 Polygonum multiflorum Species Polygonaceae Eukaryota roots n.a. n.a. PMID[24499304]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota aerial parts herbal garden of Chungbuk National University, Cheongju, Korea 2012-Oct PMID[24963714]
NPO31136 Cassia tora Species Fabaceae Eukaryota seeds n.a. n.a. PMID[26483136]
NPO23736 Myrsine africana Species Primulaceae Eukaryota root n.a. n.a. PMID[2778455]
NPO23736 Myrsine africana Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[29300477]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota Roots n.a. n.a. PMID[29359942]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota Roots n.a. n.a. PMID[31944695]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota Roots; Tubers n.a. n.a. PMID[7714535]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[8277318]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota Rhizomes n.a. n.a. PMID[8482946]
NPO29836 Cassia obtusifolia Species Fabaceae Eukaryota n.a. seed n.a. PMID[9810700]
NPO23736 Myrsine africana Species Primulaceae Eukaryota n.a. fruit n.a. Database[Article]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota n.a. aerial part n.a. Database[Article]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO13418 Rumex acetosa Species Polygonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO13418 Rumex acetosa Species Polygonaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO13418 Rumex acetosa Species Polygonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO13054 Rhamnus davurica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29334 Oplopanax elatus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31520 Polygonum multiflorum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15308 Stigma croci n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO26212 Fagopyrum tataricum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25658 Rumex japonicus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3004 Ventilago calyculata Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24601 Rumex dentatus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23736 Myrsine africana Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO574 Rumex nepalensis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18339 Rheum wittrocki Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31365 Cephaelis ipecacuanha Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12955 Rumex crispus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30179 Cassia occidentalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23368 Caulis sargentodoxae n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO31136 Cassia tora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18681 Artemisia scoparia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27678 Boehmeria platanifolia Species Urticaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13418 Rumex acetosa Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30326 Polygonum perfoliatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11192 Hedera helix Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30631 Rhamnus frangula Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30021 Rheum emodi Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13107 Rumex patientia Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10994 Sargentodoxa cuneata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29836 Cassia obtusifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7026 Vismia orientalis Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1475.1 Lilium brownii var. viridulum Varieties Liliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23982 Ventilago leiocarpa Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12759 Rheum australe Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10994 Sargentodoxa cuneata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3004 Ventilago calyculata Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2690 Carapichea ipecacuanha Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13107 Rumex patientia Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23982 Ventilago leiocarpa Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27678 Boehmeria platanifolia Species Urticaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27034 Radix et rhizoma rhei praeparata Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4195 Radix et rhizoma rhei Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29334 Oplopanax elatus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12955 Rumex crispus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO574 Rumex nepalensis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5990 Frangula alnus Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24601 Rumex dentatus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26212 Fagopyrum tataricum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7672 Senna tora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18339 Rheum wittrocki Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7026 Vismia orientalis Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12327 Senna occidentalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26294 Rhizoma dioscoreae hypoglaucae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11192 Hedera helix Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13418 Rumex acetosa Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15308 Stigma croci n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO12834 Radix polygoni multiflori preparata Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11222 Rubus alceifolius Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8921 Senna obtusifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23368 Caulis sargentodoxae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15018.1 Dioscorea collettii var. hypoglauca Varieties Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13054 Rhamnus davurica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9721 Radix moghaniae philippinensis Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25430 Xanthoceras sorbifolium Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25658 Rumex japonicus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18681 Artemisia scoparia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23736 Myrsine africana Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1475.1 Lilium brownii var. viridulum Varieties Liliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18030 Herba acalyphae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO6826 Persicaria perfoliata Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9148 Caulis polygoni multiflori n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO25628 Abrus pulchellus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18339 Rheum wittrocki Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10994 Sargentodoxa cuneata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31520 Polygonum multiflorum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18681 Artemisia scoparia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30179 Cassia occidentalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29334 Oplopanax elatus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13054 Rhamnus davurica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24601 Rumex dentatus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31136 Cassia tora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO574 Rumex nepalensis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28024 Rheum palmatum Species Polygonaceae 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]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11192 Hedera helix Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29836 Cassia obtusifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25658 Rumex japonicus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13107 Rumex patientia Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30631 Rhamnus frangula Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20881 Rheum officinale Species Polygonaceae 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]
NPO6826 Persicaria perfoliata Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7672 Senna tora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8921 Senna obtusifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2690 Carapichea ipecacuanha Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10994 Sargentodoxa cuneata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25658 Rumex japonicus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12327 Senna occidentalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13054 Rhamnus davurica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO574 Rumex nepalensis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15018.1 Dioscorea collettii var. hypoglauca Varieties Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12759 Rheum australe Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25430 Xanthoceras sorbifolium Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12955 Rumex crispus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11222 Rubus alceifolius Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23982 Ventilago leiocarpa Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13418 Rumex acetosa Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10994 Sargentodoxa cuneata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11192 Hedera helix Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27678 Boehmeria platanifolia Species Urticaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6826 Persicaria perfoliata Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3004 Ventilago calyculata Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7672 Senna tora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2690 Carapichea ipecacuanha Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29334 Oplopanax elatus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18681 Artemisia scoparia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26212 Fagopyrum tataricum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25658 Rumex japonicus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13107 Rumex patientia Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5990 Frangula alnus Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8921 Senna obtusifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25628 Abrus pulchellus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7026 Vismia orientalis Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23736 Myrsine africana Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24601 Rumex dentatus Species Polygonaceae 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

☑ 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 NPC254848 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

  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 NPC254848 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

  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