NPASS Compound

Natural Product: NPC95427

Natural Product ID	NPC95427
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ORJDDOBAOGKRJV-CQSZACIVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6950539
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

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

Chemical Representations

RDKit 3D 34 36 0 0 0 0 0 0 0 0999 V2000 -5.6079 -0.1323 1.5340 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2484 -0.0451 1.8129 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2437 -0.1454 0.8857 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5627 -0.3517 -0.4585 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5599 -0.4528 -1.3907 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2616 -0.3518 -1.0020 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2024 -0.4564 -1.9695 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4981 -0.7195 -3.1666 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2286 -0.2711 -1.6375 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3304 0.4430 -0.3312 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7102 0.5088 0.1922 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0191 1.0061 1.4415 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3134 1.0602 1.9146 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3687 0.6143 1.1506 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0749 0.1132 -0.1037 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7655 0.0616 -0.5748 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4198 -0.0561 0.6363 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9190 -0.1453 0.3382 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9286 -0.0454 1.2638 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8388 -0.6586 -2.7407 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8603 -0.8712 0.7485 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0707 0.8494 1.2645 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1638 -0.4628 2.4543 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5743 -0.4329 -0.7781 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7066 -1.2635 -1.6463 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6815 0.4025 -2.4183 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0195 1.5101 -0.5173 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1698 1.3566 2.0369 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5364 1.4519 2.8930 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3975 0.6428 1.4924 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9089 -0.2380 -0.7046 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5634 -0.3364 -1.5624 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6892 0.1127 2.2955 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9848 0.1501 -3.3529 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 10 17 1 0 17 18 1 0 18 19 2 0 5 20 1 0 19 3 1 0 18 6 1 0 16 11 1 0 1 21 1 0 1 22 1 0 1 23 1 0 4 24 1 0 9 25 1 0 9 26 1 0 10 27 1 6 12 28 1 0 13 29 1 0 14 30 1 0 15 31 1 0 16 32 1 0 19 33 1 0 20 34 1 0 M END

Standard InCHIKey	ORJDDOBAOGKRJV-CQSZACIVSA-N
Standard InCHI	InChI=1S/C16H14O4/c1-19-11-7-12(17)16-13(18)9-14(20-15(16)8-11)10-5-3-2-4-6-10/h2-8,14,17H,9H2,1H3/t14-/m1/s1
SMILES	COc1cc(c2C(=O)C[C@H](c3ccccc3)Oc2c1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	270.09	Volume:	276.329 ? Van der Waals volume.
Dense:	0.977	LogP:	3.61 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.464 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.862 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	18.0
TPSA:	55.76 ? 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:	0.911	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.59	Fsp³:	0.188
MCE-18:	51.368 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.538	Fluc inhibitor:	0.889 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.334 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.318 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.425	Promiscuous compounds:	0.061

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.854	MDCK Permeability:	-4.754
Pgp-inhibitor:	1.0	Pgp-substrate:	0.009
PAMPA:	0.054 ? 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%):	0.0	30% Bioavailability (F30%):	0.601
50% Bioavailability (F50%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017	MRP1:	0.674
Plasma Protein Binding (PPB):	98.332%	Volume Distribution (VD):	0.287
Fu:	1.356% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.998
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.92	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.018	CYP2C19-substrate:	0.966
CYP2C9-inhibitor:	0.534	CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.073	CYP2D6-substrate:	0.391
CYP3A4-inhibitor:	0.004	CYP3A4-substrate:	0.007
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.666
HLM stability:	0.99 ? 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):

5.459

Half-life (T1/2):

1.045

ADMET: Toxicity

hERG Blockers:	0.146	hERG Blockers (10um):	0.51
Human Hepatotoxicity (H-HT):	0.774	Drug-induced Liver Injury (DILI):	0.538
AMES Toxicity:	0.734	Rat Oral Acute Toxicity:	0.497
Maximum Recommended Daily Dose:	0.548	Skin Sensitization:	0.664
Carcinogencity:	0.526	Eye Corrosion:	0.029
Eye Irritation:	0.99	Respiratory Toxicity:	0.213
Drug-induced Neurotoxicity:	0.874	Ototoxicity:	0.371
Hematotoxicity:	0.304	Drug-induced Nephrotoxicity:	0.808
Genotoxicity:	0.749	RPMI-8226 Immunitoxicity:	0.142
A549 Cytotoxicity:	0.311	Hek293 Cytotoxicity:	0.343
BCF:	1.599 ? 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:	4.086 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.657 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.801 ? 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
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[10514313]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[10514313]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654416]
NPO27986	Lonchocarpus chiricanus	Species	Fabaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[11421729]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[11575962]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	seed	n.a.	PMID[14577694]
NPO27695	Centaurea sonchifolia	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1624943]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[16643038]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	rhizomes	Pindaya Township, Shan State, Myanmar	2004-NOV	PMID[17896818]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[18177011]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271742]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20014777]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20038159]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506820]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20590154]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	seed	n.a.	PMID[21942765]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	seeds	n.a.	n.a.	PMID[21942765]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22459211]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	aerial part	n.a.	n.a.	PMID[25442304]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27508308]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[28099006]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31664789]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32872604]
NPO19745	Esox lucius	Species	Esocidae	Eukaryota	n.a.	n.a.	n.a.	PMID[3349210]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36352904]
NPO4164	Salvia virgata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38611827]
NPO28385	Iris kashmiriana	Species	Tarachodidae	Eukaryota	n.a.	n.a.	n.a.	PMID[39433747]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39679248]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39680258]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8064299]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176404]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28412	Amorphophallus konjac	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27986	Lonchocarpus chiricanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28206	Aniba santalodora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28003	Astragalus circassicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28063	Beilschmiedia madang	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8961	Bethencourtia palmensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27882	Boswellia ovalifoliolata	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25499	Campanula choziatowskyi	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17337	Centaurea scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27695	Centaurea sonchifolia	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1184	Colchicum filifolium	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11849	Cynoglossum macrostylum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26342	Dialium excelsum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27397	Drymaria cordata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27455	Dysidea fragilis	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28044	Erythrina hypaphorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19745	Esox lucius	Species	Esocidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28426	Etmopterus spinax	Species	Etmopteridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27145	Euphorbia hylonoma	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27916	Hardenbergia violacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27637	Heliotropium scabrum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27613	Helleborus macranthus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28385	Iris kashmiriana	Species	Tarachodidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19383	Lactarius mitissimus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26553	Lemonia spectabilis	Species	Lemoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9354	Lepechinia urbanii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27702	Matricaria sabulosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27057	Matsucoccus josephi	Species	Margarodidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28313	Mentzelia decapetala	Species	Loasaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2030	Mimosa pigra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16156	Mucuna holtonii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28289	Nepytia freemani	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27506	Orgyia pseudotsugata	Species	Lymantriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25835	Parmotrema nilgherrense	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5970.1	Petunia axillaris subsp. parodii	Subspecies	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27642	Podocarpus dacrydioides	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26476	Preussia terricola	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27816	Pterocaulon serrulatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16298	Quercus marilandica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27614	Salix rosmarinifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28083	Salvia lavanduloides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26321	Salvia patens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4164	Salvia virgata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27338	Senecio platyphylloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27854	Sphaeria rousseliana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27234	Thalassiosira weissflogii	Species	Thalassiosiraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19745	Esox lucius	Species	Esocidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO19745	Esox lucius	Species	Esocidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27882	Boswellia ovalifoliolata	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27397	Drymaria cordata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26342	Dialium excelsum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16298	Quercus marilandica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25835	Parmotrema nilgherrense	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19745	Esox lucius	Species	Esocidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27854	Sphaeria rousseliana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27600	Boesenbergia pandurata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27916	Hardenbergia violacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26476	Preussia terricola	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27882	Boswellia ovalifoliolata	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27338	Senecio platyphylloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27816	Pterocaulon serrulatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17337	Centaurea scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28313	Mentzelia decapetala	Species	Loasaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28206	Aniba santalodora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28083	Salvia lavanduloides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1184	Colchicum filifolium	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27642	Podocarpus dacrydioides	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27057	Matsucoccus josephi	Species	Margarodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27145	Euphorbia hylonoma	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28289	Nepytia freemani	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27986	Lonchocarpus chiricanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28063	Beilschmiedia madang	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27613	Helleborus macranthus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27637	Heliotropium scabrum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8961	Bethencourtia palmensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27397	Drymaria cordata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27702	Matricaria sabulosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9354	Lepechinia urbanii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27695	Centaurea sonchifolia	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4164	Salvia virgata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28385	Iris kashmiriana	Species	Tarachodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27455	Dysidea fragilis	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27234	Thalassiosira weissflogii	Species	Thalassiosiraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26553	Lemonia spectabilis	Species	Lemoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26321	Salvia patens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28003	Astragalus circassicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19383	Lactarius mitissimus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28426	Etmopterus spinax	Species	Etmopteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28412	Amorphophallus konjac	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2030	Mimosa pigra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25499	Campanula choziatowskyi	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28044	Erythrina hypaphorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16156	Mucuna holtonii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5970.1	Petunia axillaris subsp. parodii	Subspecies	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11849	Cynoglossum macrostylum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27506	Orgyia pseudotsugata	Species	Lymantriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27614	Salix rosmarinifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	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

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

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 NPC95427 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	23797
0.1-0.2	21115
0.2-0.3	4151
0.3-0.4	516
0.4-0.5	178
0.5-0.6	63
0.6-0.7	23
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC150648
0.8444	Intermediate Similarity	NPC6407
0.8444	Intermediate Similarity	NPC545184
0.8085	Intermediate Similarity	NPC329203
0.8085	Intermediate Similarity	NPC222342
0.74	Intermediate Similarity	NPC18727
0.7347	Intermediate Similarity	NPC73028
0.7234	Intermediate Similarity	NPC140890
0.6939	Remote Similarity	NPC243083
0.6939	Remote Similarity	NPC13768
0.6939	Remote Similarity	NPC287246
0.68	Remote Similarity	NPC37392
0.6786	Remote Similarity	NPC477840
0.6731	Remote Similarity	NPC310135
0.6667	Remote Similarity	NPC255106
0.6667	Remote Similarity	NPC194432
0.6667	Remote Similarity	NPC235165
0.6531	Remote Similarity	NPC265871
0.6531	Remote Similarity	NPC205093
0.6471	Remote Similarity	NPC312391
0.6346	Remote Similarity	NPC274784
0.6346	Remote Similarity	NPC482119
0.6346	Remote Similarity	NPC20709
0.6346	Remote Similarity	NPC482120
0.6327	Remote Similarity	NPC485642
0.6327	Remote Similarity	NPC611561
0.6275	Remote Similarity	NPC204515
0.619	Remote Similarity	NPC97052
0.6154	Remote Similarity	NPC177354
0.6038	Remote Similarity	NPC99597
0.6038	Remote Similarity	NPC122828
0.5962	Remote Similarity	NPC482487
0.5862	Remote Similarity	NPC109183
0.5862	Remote Similarity	NPC39045
0.5833	Remote Similarity	NPC228184
0.5818	Remote Similarity	NPC469758
0.5769	Remote Similarity	NPC476480
0.5769	Remote Similarity	NPC28753
0.5769	Remote Similarity	NPC188243
0.5769	Remote Similarity	NPC213322
0.5769	Remote Similarity	NPC110228
0.5769	Remote Similarity	NPC84585
0.5763	Remote Similarity	NPC175504
0.5741	Remote Similarity	NPC215885
0.5741	Remote Similarity	NPC110038
0.5667	Remote Similarity	NPC470131
0.5667	Remote Similarity	NPC470132
0.566	Remote Similarity	NPC32441
0.566	Remote Similarity	NPC482121
0.566	Remote Similarity	NPC79943
0.566	Remote Similarity	NPC270964
0.5636	Remote Similarity	NPC475267
0.5606	Remote Similarity	NPC219163
0.56	Remote Similarity	NPC99854
0.5593	Remote Similarity	NPC1089
0.5574	Remote Similarity	NPC480158
0.5536	Remote Similarity	NPC2416
0.5472	Remote Similarity	NPC225153
0.5472	Remote Similarity	NPC479876
0.5455	Remote Similarity	NPC480993
0.5455	Remote Similarity	NPC338131
0.5439	Remote Similarity	NPC302950
0.537	Remote Similarity	NPC248372
0.5357	Remote Similarity	NPC606248
0.5306	Remote Similarity	NPC314329
0.5306	Remote Similarity	NPC603208
0.5273	Remote Similarity	NPC20354
0.5273	Remote Similarity	NPC484336
0.5273	Remote Similarity	NPC162869
0.5273	Remote Similarity	NPC484337
0.5263	Remote Similarity	NPC48208
0.5263	Remote Similarity	NPC271590
0.5263	Remote Similarity	NPC599987
0.5263	Remote Similarity	NPC601395
0.5254	Remote Similarity	NPC236637
0.5246	Remote Similarity	NPC3642
0.5185	Remote Similarity	NPC22467
0.5185	Remote Similarity	NPC182421
0.5179	Remote Similarity	NPC107586
0.5179	Remote Similarity	NPC156057
0.5179	Remote Similarity	NPC110776
0.5179	Remote Similarity	NPC324386
0.5161	Remote Similarity	NPC176229
0.5161	Remote Similarity	NPC470133
0.5161	Remote Similarity	NPC470135
0.5147	Remote Similarity	NPC39351
0.5088	Remote Similarity	NPC321011
0.5088	Remote Similarity	NPC294852
0.5088	Remote Similarity	NPC476153
0.5088	Remote Similarity	NPC469764
0.5088	Remote Similarity	NPC188679
0.5085	Remote Similarity	NPC35150
0.5085	Remote Similarity	NPC106328
0.5079	Remote Similarity	NPC316816

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC95427 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3508
0.1-0.2	5325
0.2-0.3	301
0.3-0.4	9
0.4-0.5	3
0.5-0.6	3
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6939	Remote Similarity	NPD1550	Phase 2
0.566	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.5439	Remote Similarity	NPD1934	Phase 0
0.5306	Remote Similarity	NPD1547	Clinical (unspecified phase)

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