NPASS Compound

Natural Product: NPC265624

Natural Product ID	NPC265624
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ginkgetin
IUPAC Name	5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)chromen-4-one
Synonyms	Ginkgetin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL377324
PubChem CID	5271805
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 64 69 0 0 0 0 0 0 0 0999 V2000 -7.2652 3.7919 0.9539 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2632 3.4665 -0.4017 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2952 2.6341 -0.9446 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3530 2.3569 -2.2798 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4158 1.5351 -2.8722 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4155 0.9969 -2.0854 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4472 0.1619 -2.6380 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4828 -0.1060 -3.8674 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4748 -0.3428 -1.7963 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4243 -0.0598 -0.4580 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4176 -0.5704 0.4633 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4526 -0.2217 1.8164 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5138 -0.6907 2.7059 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5054 -1.5257 2.3075 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5577 -1.8808 0.9802 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3900 -1.4050 0.0923 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6251 -2.7621 0.5346 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4158 -4.1182 0.5607 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4410 -4.9355 0.1339 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6425 -4.4153 -0.3071 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8086 -3.0331 -0.3155 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9835 -2.4490 -0.7437 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9204 -3.1879 -1.1334 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0846 -1.0618 -0.7269 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0635 -0.2511 -0.3020 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1414 1.2074 -0.2735 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0747 1.9688 0.1671 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1432 3.3390 0.1957 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2797 3.9914 -0.2150 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3493 3.2673 -0.6552 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2598 1.8841 -0.6762 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3352 5.3915 -0.1803 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9658 -0.8742 0.0950 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8125 -2.1772 0.1017 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6838 -5.2121 -0.7392 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1944 -4.6639 1.0083 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4552 -1.9923 3.2406 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3936 -1.6247 4.5917 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3614 0.7328 0.0119 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3135 1.2462 -0.7320 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2830 2.0806 -0.1854 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4858 1.2632 -4.2222 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2729 4.1201 1.3122 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9969 4.6252 1.1261 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6331 2.9103 1.5513 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1442 2.7880 -2.8796 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7332 -0.9867 -2.2375 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2530 0.4343 2.1302 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5351 -0.4215 3.7680 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3636 -1.6774 -0.9678 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2781 -5.9965 0.1540 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9989 -0.5997 -1.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1897 1.4358 0.4860 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3183 3.9463 0.5372 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2605 3.7488 -0.9862 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1394 1.3753 -1.0348 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2596 5.8492 -0.1737 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5759 -5.9692 -1.4132 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1806 -5.4549 0.4980 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1777 -2.1586 5.1326 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3570 -1.8911 4.9484 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5151 -0.5091 4.6888 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2221 2.2892 0.8725 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8175 0.3878 -4.5616 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 2 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 15 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 29 32 1 0 25 33 1 0 33 34 1 0 20 35 1 0 18 36 1 0 14 37 1 0 37 38 1 0 10 39 1 0 39 40 1 0 40 41 2 0 5 42 1 0 41 3 1 0 40 6 1 0 16 11 1 0 34 17 1 0 34 21 2 0 31 26 1 0 1 43 1 0 1 44 1 0 1 45 1 0 4 46 1 0 9 47 1 0 12 48 1 0 13 49 1 0 16 50 1 0 19 51 1 0 24 52 1 0 27 53 1 0 28 54 1 0 30 55 1 0 31 56 1 0 32 57 1 0 35 58 1 0 36 59 1 0 38 60 1 0 38 61 1 0 38 62 1 0 41 63 1 0 42 64 1 0 M END

Standard InCHIKey	AIFCFBUSLAEIBR-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C32H22O10/c1-39-18-10-20(34)30-23(37)13-27(41-28(30)11-18)16-5-8-25(40-2)19(9-16)29-21(35)12-22(36)31-24(38)14-26(42-32(29)31)15-3-6-17(33)7-4-15/h3-14,33-36H,1-2H3
SMILES	COc1cc(c2c(=O)cc(c3ccc(c(c3)c3c(cc(c4c(=O)cc(c5ccc(cc5)O)oc34)O)O)OC)oc2c1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	566.12	Volume:	556.408 ? Van der Waals volume.
Dense:	1.017	LogP:	4.272 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.755 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.469 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	36.0
TPSA:	159.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.203	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.984	Fsp³:	0.062
MCE-18:	36.0 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.996	Fluc inhibitor:	0.418 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.972 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.998 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.359	Promiscuous compounds:	0.936

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.996	MDCK Permeability:	-4.779
Pgp-inhibitor:	0.136	Pgp-substrate:	0.293
PAMPA:	0.224 ? 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):	0.002
20% Bioavailability (F20%):	0.189	30% Bioavailability (F30%):	0.703
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.932
Plasma Protein Binding (PPB):	97.564%	Volume Distribution (VD):	-0.22
Fu:	1.764% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.985
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.971
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	0.175	CYP1A2-substrate:	0.188
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.869	CYP2C9-substrate:	0.908
CYP2D6-inhibitor:	0.999	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.934 ? 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):

1.801

Half-life (T1/2):

1.767

ADMET: Toxicity

hERG Blockers:	0.095	hERG Blockers (10um):	0.472
Human Hepatotoxicity (H-HT):	0.471	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.784	Rat Oral Acute Toxicity:	0.609
Maximum Recommended Daily Dose:	0.975	Skin Sensitization:	0.255
Carcinogencity:	0.886	Eye Corrosion:	0.001
Eye Irritation:	0.982	Respiratory Toxicity:	0.894
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.058
Hematotoxicity:	0.061	Drug-induced Nephrotoxicity:	0.023
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.131
A549 Cytotoxicity:	0.622	Hek293 Cytotoxicity:	0.945
BCF:	1.271 ? 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:	4.579 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.125 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.804 ? 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
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12081149]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542368]
NPO2284	Cephalotaxus koreana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16574412]
NPO2284	Cephalotaxus koreana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17994703]
NPO6895	Elateriospermum tapos	Species	Euphorbiaceae	Eukaryota	leaves and stem	Nakorn Si Thammarat Province, Thailand	2004-MAR	PMID[18179177]
NPO21757	Selaginella moellendorfii	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19422203]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19757853]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21370894]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	root	n.a.	PMID[22051934]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	aerial parts	herbal garden of Chungbuk National University, Cheongju, Korea	2012-Oct	PMID[24963714]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28139925]
NPO21757	Selaginella moellendorfii	Species	Selaginellaceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[29412669]
NPO11132	Alangium longiflorum	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30106296]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184894]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[8482946]
NPO21757	Selaginella moellendorfii	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9134745]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	aerial part	n.a.	Database[Article]
NPO10874	Selaginella sanguinolenta	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO563	Leucopaxillus cerealis	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28466	Torreya nucifera	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11819	Trichophyton megnini	Species	Arthrodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15125.1	Taxus wallichiana var. chinensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10487	Rosa americana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22296	Rheum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11936	Ptilocaulis walpersi	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10953	Papaver strigosum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27451	Ophiocordyceps sinensis	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21703	Maianthemum atropurpureum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2284	Cephalotaxus koreana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10084	Equisetum hyemale	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3362	Dictyostelium mucoroides	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12272	Calceolaria petiolaris	Species	Calceolariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7785	Boletus fomentarius	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11132	Alangium longiflorum	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28635	Cephalotaxus harringtonia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30166	Dacrydium sp	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28635	Cephalotaxus harringtonia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10421	Selaginella braunii	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3583	Selaginella stauntoniana	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21757	Selaginella moellendorfii	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10874	Selaginella sanguinolenta	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10874	Selaginella sanguinolenta	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21757	Selaginella moellendorfii	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1010	Dacrydium sp.	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10084	Equisetum hyemale	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28635	Cephalotaxus harringtonia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3583	Selaginella stauntoniana	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27451	Ophiocordyceps sinensis	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10421	Selaginella braunii	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27231	Herba selaginellae doederleinii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO15125.1	Taxus wallichiana var. chinensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	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]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	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]
NPO27451	Ophiocordyceps sinensis	Species	Ophiocordycipitaceae	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]
NPO10084	Equisetum hyemale	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	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]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11819	Trichophyton megnini	Species	Arthrodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7785	Boletus fomentarius	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12272	Calceolaria petiolaris	Species	Calceolariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10084	Equisetum hyemale	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21703	Maianthemum atropurpureum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15125.1	Taxus wallichiana var. chinensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12615	Athrotaxis selaginoides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27451	Ophiocordyceps sinensis	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11936	Ptilocaulis walpersi	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3362	Dictyostelium mucoroides	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO563	Leucopaxillus cerealis	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11132	Alangium longiflorum	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10487	Rosa americana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10953	Papaver strigosum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10874	Selaginella sanguinolenta	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22296	Rheum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2284	Cephalotaxus koreana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28635	Cephalotaxus harringtonia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28466	Torreya nucifera	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6895	Elateriospermum tapos	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21757	Selaginella moellendorfii	Species	Selaginellaceae	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

Activity Type	# Activity
IC50	8
logIC50	1
Inhibition	4
Activity	50

Activity Type	# Activity
Individual protein	6
Cell line	39
Unchecked	13
Others	3
Organism	1
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1602	Individual protein	Neuraminidase	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	=	55.0	ug.mL-1	PMID[20116898]
NPT1602	Individual protein	Neuraminidase	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	logIC50	=	1.74	n.a.	PMID[20116898]
NPT740	Individual protein	Beta-secretase 1	Homo sapiens	IC50	=	4180.0	nM	PMID[20598535]
NPT5467	Individual protein	Protein-tyrosine phosphatase 4A3	Homo sapiens	IC50	=	25800.0	nM	PMID[33766767]
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Inhibition	n.a.	n.a.	%	PMID[36700552]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1309	Cell line	Osteoblasts	n.a.	Activity	=	69.3	%	PMID[16574412]
NPT1309	Cell line	Osteoblasts	n.a.	Activity	=	116.8	%	PMID[16574412]
NPT1309	Cell line	Osteoblasts	n.a.	Activity	=	39.9	%	PMID[16574412]
NPT377	Cell line	OVCAR-3	Homo sapiens	IC50	=	1.8	ug.mL-1	PMID[9134745]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	43.1	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	45.3	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	0.99	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	67.6	%	PMID[36700552]
NPT2170	Cell line	RKO	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	10.5	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	58.1	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	39.2	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	51.2	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	25.8	%	PMID[36700552]
NPT323	Cell line	SW-620	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	5.69	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	3.37	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	1.2	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	55.4	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	0.54	%	PMID[36700552]
NPT114	Cell line	LoVo	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[36700552]
NPT139	Cell line	HT-29	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	1.47	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	52.1	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	33.6	%	PMID[36700552]
NPT28438	Unchecked	Unchecked	n.a.	Activity	n.a.	n.a.	n.a.	PMID[36700552]
NPT28438	Unchecked	Unchecked	n.a.	Inhibition	n.a.	n.a.	%	PMID[36700552]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	2800.0	nM	PMID[22989363]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	59.8	%	PMID[26004578]
NPT2	Others	Unspecified	n.a.	IC50	=	55.0	ug.mL-1	PMID[17110111]
NPT2	Others	Unspecified	n.a.	IC50	=	9.78	ug.mL-1	PMID[17110111]
NPT2	Others	Unspecified	n.a.	IC50	>	100.0	ug.mL-1	PMID[17110111]

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 NPC265624 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	30547
0.1-0.2	16482
0.2-0.3	1919
0.3-0.4	656
0.4-0.5	194
0.5-0.6	34
0.6-0.7	13
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8971	High Similarity	NPC14606
0.8286	Intermediate Similarity	NPC71061
0.8169	Intermediate Similarity	NPC194593
0.7917	Intermediate Similarity	NPC159707
0.7808	Intermediate Similarity	NPC121649
0.7639	Intermediate Similarity	NPC150908
0.7467	Intermediate Similarity	NPC205026
0.7403	Intermediate Similarity	NPC55443
0.7105	Intermediate Similarity	NPC215203
0.7027	Intermediate Similarity	NPC248739
0.697	Remote Similarity	NPC234133
0.6933	Remote Similarity	NPC603508
0.6795	Remote Similarity	NPC18699
0.6623	Remote Similarity	NPC303485
0.6623	Remote Similarity	NPC158027
0.6538	Remote Similarity	NPC186227
0.641	Remote Similarity	NPC72425
0.6324	Remote Similarity	NPC29353
0.6203	Remote Similarity	NPC290830
0.6173	Remote Similarity	NPC601565
0.6	Remote Similarity	NPC138299
0.6	Remote Similarity	NPC485523
0.6	Remote Similarity	NPC600396
0.5972	Remote Similarity	NPC124784
0.597	Remote Similarity	NPC222713
0.5915	Remote Similarity	NPC108406
0.589	Remote Similarity	NPC610914
0.5875	Remote Similarity	NPC601984
0.5857	Remote Similarity	NPC127447
0.5753	Remote Similarity	NPC195202
0.5753	Remote Similarity	NPC223579
0.5679	Remote Similarity	NPC600972
0.5676	Remote Similarity	NPC137062
0.5652	Remote Similarity	NPC485524
0.56	Remote Similarity	NPC67322
0.5556	Remote Similarity	NPC231772
0.5556	Remote Similarity	NPC143799
0.5375	Remote Similarity	NPC254351
0.5357	Remote Similarity	NPC272064
0.5342	Remote Similarity	NPC33265
0.5342	Remote Similarity	NPC48479
0.5287	Remote Similarity	NPC27942
0.5244	Remote Similarity	NPC259757
0.5205	Remote Similarity	NPC52611
0.5143	Remote Similarity	NPC50898
0.5135	Remote Similarity	NPC198826
0.5135	Remote Similarity	NPC250266
0.5135	Remote Similarity	NPC146679
0.5135	Remote Similarity	NPC120163
0.5132	Remote Similarity	NPC177298
0.5125	Remote Similarity	NPC288840
0.5116	Remote Similarity	NPC39360
0.5116	Remote Similarity	NPC29763
0.5116	Remote Similarity	NPC210003
0.5111	Remote Similarity	NPC604941
0.5067	Remote Similarity	NPC78913
0.506	Remote Similarity	NPC606549

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC265624 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5995
0.1-0.2	3090
0.2-0.3	54
0.3-0.4	8
0.4-0.5	3
0.5-0.6	0
0.6-0.7	0
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
		NPD

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