NPASS Compound

Natural Product: NPC102256

Natural Product ID	NPC102256
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Schizandrin
IUPAC Name	n.a.
Synonyms	Schisandrin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL253688
PubChem CID	3001664
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 63 65 0 0 0 0 0 0 0 0999 V2000 0.0148 4.7653 -0.0983 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3899 3.8898 0.9381 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8890 2.6571 0.5845 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2654 2.4551 0.3511 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1208 3.5300 0.4837 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5007 3.3363 0.2517 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7442 1.2097 -0.0020 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9028 0.1754 -0.1305 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5393 0.3945 0.1001 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0094 1.6097 0.4609 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3431 1.6792 0.6858 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9324 1.4581 1.9601 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6362 -0.4624 -0.0251 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9077 -1.7458 0.4654 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1682 -2.2252 0.2226 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1100 -1.4731 -0.4711 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7721 -0.1957 -0.9400 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5206 0.3245 -0.7222 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0758 1.5544 -1.1581 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4629 1.7611 -2.4201 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6859 0.5841 -1.6372 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5693 1.4904 -1.0212 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3729 -1.9444 -0.7150 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7601 -3.2306 -0.2602 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0919 -2.7446 1.1609 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2557 -2.9834 0.5550 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3169 -2.0019 0.7151 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6396 -1.0897 -0.4582 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6263 -2.7345 1.0037 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0707 -1.2442 1.8852 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0069 -3.2627 -0.9370 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2522 5.8193 0.1186 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4686 4.4801 -1.0523 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1068 4.6110 -0.2304 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9166 2.4975 0.8480 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7027 3.0694 -0.8176 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0959 4.2316 0.5028 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8071 1.0212 -0.1871 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9292 1.9179 2.0386 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0501 0.3717 2.0765 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2112 1.8121 2.7271 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4002 -3.2158 0.5943 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6369 2.7576 -2.8327 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6112 1.4861 -2.3719 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9242 0.9855 -3.0996 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9248 1.1039 -0.0346 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1171 2.4823 -0.8515 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4649 1.6478 -1.6735 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7259 -3.2037 0.8495 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9808 -3.9397 -0.6397 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7661 -3.5090 -0.5697 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0391 -2.4188 2.2134 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6238 -3.7200 1.1966 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5986 -3.9627 0.9583 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2460 -1.4462 -1.4087 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7133 -0.8186 -0.4913 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5851 -3.2639 1.9767 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4538 -2.0217 0.9857 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8200 -3.4717 0.1863 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9434 -0.7802 2.0723 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3653 -4.1718 -1.0490 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9313 -3.4603 -1.4727 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4582 -2.4270 -1.3903 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 1 0 4 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 9 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 17 21 1 0 21 22 1 0 16 23 1 0 23 24 1 0 14 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 27 30 1 1 26 31 1 0 10 3 1 0 18 13 1 0 28 8 1 0 1 32 1 0 1 33 1 0 1 34 1 0 6 35 1 0 6 36 1 0 6 37 1 0 7 38 1 0 12 39 1 0 12 40 1 0 12 41 1 0 15 42 1 0 20 43 1 0 20 44 1 0 20 45 1 0 22 46 1 0 22 47 1 0 22 48 1 0 24 49 1 0 24 50 1 0 24 51 1 0 25 52 1 0 25 53 1 0 26 54 1 1 28 55 1 0 28 56 1 0 29 57 1 0 29 58 1 0 29 59 1 0 30 60 1 0 31 61 1 0 31 62 1 0 31 63 1 0 M END

Standard InCHIKey	YEFOAORQXAOVJQ-RZFZLAGVSA-N
Standard InCHI	InChI=1S/C24H32O7/c1-13-9-14-10-16(26-3)20(28-5)22(30-7)18(14)19-15(12-24(13,2)25)11-17(27-4)21(29-6)23(19)31-8/h10-11,13,25H,9,12H2,1-8H3/t13-,24-/m0/s1
SMILES	COc1c(OC)cc2c(c1OC)c1c(cc(c(c1OC)OC)OC)C[C@@H]([C@@](C2)(C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	432.21	Volume:	443.704 ? Van der Waals volume.
Dense:	0.974	LogP:	2.372 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.795 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.107 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	18.0
TPSA:	75.61 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.742	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.444	Fsp³:	0.5
MCE-18:	74.111 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.026	Fluc inhibitor:	0.331 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.262 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.248 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.264	Promiscuous compounds:	0.573

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.576	MDCK Permeability:	-4.57
Pgp-inhibitor:	0.052	Pgp-substrate:	0.229
PAMPA:	0.077 ? 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):	0.0
20% Bioavailability (F20%):	0.008	30% Bioavailability (F30%):	0.002
50% Bioavailability (F50%):	0.187

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.28	MRP1:	0.999
Plasma Protein Binding (PPB):	77.893%	Volume Distribution (VD):	0.078
Fu:	23.265% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.991
OATP1B3 inhibitor:	0.988	BCRP inhibitor:	0.056
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.964	CYP1A2-substrate:	0.022
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.356
CYP2C9-inhibitor:	0.058	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.028	CYP2D6-substrate:	0.926
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.983
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.964
HLM stability:	0.406 ? 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):

3.914

Half-life (T1/2):

1.223

ADMET: Toxicity

hERG Blockers:	0.242	hERG Blockers (10um):	0.514
Human Hepatotoxicity (H-HT):	0.662	Drug-induced Liver Injury (DILI):	0.336
AMES Toxicity:	0.405	Rat Oral Acute Toxicity:	0.449
Maximum Recommended Daily Dose:	0.606	Skin Sensitization:	0.772
Carcinogencity:	0.896	Eye Corrosion:	0.011
Eye Irritation:	0.646	Respiratory Toxicity:	0.824
Drug-induced Neurotoxicity:	0.72	Ototoxicity:	0.522
Hematotoxicity:	0.484	Drug-induced Nephrotoxicity:	0.468
Genotoxicity:	0.082	RPMI-8226 Immunitoxicity:	0.204
A549 Cytotoxicity:	0.576	Hek293 Cytotoxicity:	0.581
BCF:	1.778 ? 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:	3.412 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.171 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.858 ? 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
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11599360]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[16494492]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16494492]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562834]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17489633]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	stems	Honghe Prefecture of Yunnan Province, China	2005-Oct	PMID[18278869]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	leaves and stems	n.a.	n.a.	PMID[20146529]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21232955]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381697]
NPO33401	schisandra sphenathera	Species	Schisandraceae	Eukaryota	stems	n.a.	n.a.	PMID[23237974]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO29191	Schisandra neglecta	Species	Schisandraceae	Eukaryota	Stems	Luoji Mountain Village, Xichang County, Sicuan Province, China	2011-Sep	PMID[23738539]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[24155209]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24959987]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25302569]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37120447]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4582	Baphicacanthus cusia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8075	Cacospongia scalaris	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2263	Croton megistocarpus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO433	Geranium sibiricum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4593	Lagerstroemia indica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14100	Persea kusanoi	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7639	Senecio isatideus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO433	Geranium sibiricum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4593	Lagerstroemia indica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4582	Baphicacanthus cusia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4582	Baphicacanthus cusia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4593	Lagerstroemia indica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO433	Geranium sibiricum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4593	Lagerstroemia indica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4582	Baphicacanthus cusia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8075	Cacospongia scalaris	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14100	Persea kusanoi	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4582	Baphicacanthus cusia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29191	Schisandra neglecta	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4593	Lagerstroemia indica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7639	Senecio isatideus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO433	Geranium sibiricum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2263	Croton megistocarpus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	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
Potency	4
IC50	27
EC50	1
Inhibition	1
Activity	1
Survival	1

Activity Type	# Activity
Individual protein	7
Cell line	21
Organism	3
Others	2
Non-molecular	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1594	Individual protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	0.0005	ug.mL-1	PMID[17129588]
NPT1594	Individual protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	1.401	ug.mL-1	PMID[17129588]
NPT1594	Individual protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	0.0035	ug.mL-1	PMID[17129588]
NPT1594	Individual protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	3.135	ug.mL-1	PMID[17129588]
NPT1594	Individual protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	0.054	ug.mL-1	PMID[17129588]
NPT1594	Individual protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	0.094	ug.mL-1	PMID[17129588]
NPT54	Individual protein	Nonstructural protein 1	Influenza A virus	Potency	=	3981.1	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	61500.0	nM	PMID[18063366]
NPT1086	Cell line	SK-HEP1	Homo sapiens	IC50	=	71300.0	nM	PMID[18063366]
NPT2548	Cell line	SNU-638	Homo sapiens	IC50	=	21100.0	nM	PMID[18063366]
NPT396	Cell line	T47D	Homo sapiens	IC50	=	19800.0	nM	PMID[18063366]
NPT148	Cell line	HCT-15	Homo sapiens	IC50	=	50200.0	nM	PMID[18063366]
NPT111	Cell line	K562	Homo sapiens	IC50	=	25000.0	nM	PMID[18063366]
NPT81	Cell line	A549	Homo sapiens	IC50	=	20700.0	nM	PMID[18063366]
NPT759	Cell line	H9	Homo sapiens	IC50	>	58000.0	nM	PMID[17190445]
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[23237974]
NPT659	Cell line	SMMC-7721	Homo sapiens	IC50	>	100000.0	nM	PMID[23237974]
NPT71	Cell line	HEK293	Homo sapiens	Inhibition	=	6.2	%	PMID[24018191]
NPT71	Cell line	HEK293	Homo sapiens	IC50	=	81740.0	nM	PMID[29501940]
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	13090.0	nM	PMID[29501940]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	32560.0	nM	PMID[29501940]
NPT81	Cell line	A549	Homo sapiens	IC50	=	21650.0	nM	PMID[29501940]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	28560.0	nM	PMID[29501940]
NPT81	Cell line	A549	Homo sapiens	IC50	=	8500.0	nM	PMID[32631552]
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	5380.0	nM	PMID[32631552]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	5060.0	nM	PMID[32631552]
NPT71	Cell line	HEK293	Homo sapiens	IC50	=	80470.0	nM	PMID[32631552]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	7375.3	nM	PubChem BioAssay data set
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[23237974]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	15.8	ug.mL-1	PMID[21232955]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	3981.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Activity	=	125.0	%	PMID[25302569]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT21742	Cell line	L02	Homo sapiens	Survival	=	43.3	%	PMID[24602900]

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
-	Artemia salina	LC50	>	100.0	ug.mL-1	PMID[23237974]

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 NPC102256 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	19946
0.1-0.2	27532
0.2-0.3	2194
0.3-0.4	111
0.4-0.5	43
0.5-0.6	9
0.6-0.7	3
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8222	Intermediate Similarity	NPC53722
0.8222	Intermediate Similarity	NPC201404
0.8222	Intermediate Similarity	NPC290714
0.7872	Intermediate Similarity	NPC137352
0.7872	Intermediate Similarity	NPC183083
0.7872	Intermediate Similarity	NPC485503
0.7826	Intermediate Similarity	NPC240279
0.7292	Intermediate Similarity	NPC180602
0.7255	Intermediate Similarity	NPC328122
0.7	Intermediate Similarity	NPC55239
0.65	Remote Similarity	NPC283114
0.65	Remote Similarity	NPC207702
0.65	Remote Similarity	NPC149008
0.5957	Remote Similarity	NPC214853
0.5614	Remote Similarity	NPC295297
0.5417	Remote Similarity	NPC145722
0.5417	Remote Similarity	NPC256776
0.5417	Remote Similarity	NPC185680
0.5349	Remote Similarity	NPC471182
0.5098	Remote Similarity	NPC206737
0.5098	Remote Similarity	NPC289258
0.5098	Remote Similarity	NPC611061

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC102256 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4491
0.1-0.2	4552
0.2-0.3	102
0.3-0.4	5
0.4-0.5	0
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