NPASS Compound

Natural Product: NPC258552

Natural Product ID	NPC258552
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SLUGZPRLJCECEX-RFKUPWJGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44258787
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 86 90 0 0 0 0 0 0 0 0999 V2000 1.0265 4.3650 -0.1095 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1233 3.7509 -0.8939 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6531 2.5892 -0.5627 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1957 1.8268 0.5996 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6725 0.4772 0.1860 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5525 -0.5161 -0.1820 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0941 -1.7529 -0.5601 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7208 -1.9391 -0.5501 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1615 -0.9305 -0.1766 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5201 -1.1144 -0.1599 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9858 -2.2125 -0.4910 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4155 -0.0928 0.2234 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8553 1.0885 0.5714 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6386 2.2462 0.9808 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9758 2.4130 0.8167 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6603 3.5337 1.2764 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9980 4.5417 1.9290 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6444 4.3970 2.1064 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9821 3.2956 1.6532 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6465 5.6830 2.4069 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5200 1.2591 0.5545 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2967 0.3118 0.2034 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7803 -0.3894 0.2119 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4112 -1.0736 1.2355 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7711 -0.7092 1.6980 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8542 -1.0143 0.6844 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1948 -1.2576 -0.6465 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2135 -2.3934 -0.4900 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0325 -3.6900 -0.5699 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1244 -4.7435 -0.5284 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5244 -2.4229 0.6937 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1569 -1.6878 -1.5982 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7793 0.0290 0.6143 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9505 0.5209 2.2629 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2015 -3.1628 -0.9213 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8761 -0.2366 -0.1594 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9892 -0.9817 -0.4689 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8632 -0.3819 -1.5444 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9591 -1.4207 -1.8183 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6449 -1.8186 -0.5372 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6939 -2.0835 0.5926 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1345 -3.4751 0.5732 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2555 -4.3401 0.4864 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7564 -1.1000 0.6828 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3944 -2.9706 -0.7553 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8836 -0.8635 -2.6826 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1977 -0.1887 -2.7323 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6236 4.5041 -2.1040 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9490 5.4514 -0.3869 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0450 3.8802 -0.3371 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2643 4.3740 0.9735 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4610 2.2034 -1.1955 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4682 2.3803 1.1878 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1048 1.5979 1.2214 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7560 -2.5596 -0.8558 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5400 1.6594 0.2875 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7180 3.6325 1.1314 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1391 5.2175 2.6314 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9248 3.2111 1.8068 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5458 5.9616 2.0517 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7675 -1.2472 2.1305 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0410 -1.4433 2.5689 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3925 -1.9783 0.9315 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7341 -0.3062 -0.9858 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5493 -2.3990 -1.3862 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7146 -3.7872 0.2945 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6552 -3.7164 -1.4838 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0372 -5.1889 -1.4021 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0521 -1.4593 -1.2517 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2115 0.0595 1.5066 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7193 0.5162 2.8861 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3964 -3.9451 -0.2833 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6733 -1.9798 -0.8211 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3037 0.5599 -1.2157 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4952 -2.3300 -2.2508 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3407 -0.9949 -0.2664 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3296 -2.0046 1.5326 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5361 -3.6983 -0.3083 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5543 -3.6819 1.4952 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6461 -4.3666 1.3980 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0907 -2.9887 -0.0501 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6133 -1.0191 -3.6195 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5208 0.5105 -2.7283 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0827 3.7621 -2.7950 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3439 5.2843 -1.7941 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7551 4.9639 -2.6186 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 17 20 1 0 13 21 1 0 21 22 1 0 12 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 27 32 1 0 26 33 1 0 25 34 1 0 8 35 1 0 6 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 39 46 1 0 38 47 1 0 2 48 1 0 22 5 1 0 31 24 1 0 44 37 1 0 22 9 2 0 19 14 1 0 1 49 1 0 1 50 1 0 1 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 7 55 1 0 15 56 1 0 16 57 1 0 18 58 1 0 19 59 1 0 20 60 1 0 24 61 1 1 25 62 1 0 26 63 1 0 27 64 1 6 28 65 1 0 29 66 1 0 29 67 1 0 30 68 1 0 32 69 1 0 33 70 1 0 34 71 1 0 35 72 1 0 37 73 1 6 38 74 1 0 39 75 1 6 40 76 1 1 41 77 1 0 42 78 1 0 42 79 1 0 43 80 1 0 45 81 1 0 46 82 1 0 47 83 1 0 48 84 1 0 48 85 1 0 48 86 1 0 M END

Standard InCHIKey	SLUGZPRLJCECEX-RFKUPWJGSA-N
Standard InCHI	InChI=1S/C32H38O16/c1-12(2)3-8-15-17(44-31-26(42)24(40)21(37)18(10-33)45-31)9-16(36)20-23(39)30(28(47-29(15)20)13-4-6-14(35)7-5-13)48-32-27(43)25(41)22(38)19(11-34)46-32/h3-7,9,18-19,21-22,24-27,31-38,40-43H,8,10-11H2,1-2H3/t18?,19?,21-,22-,24+,25?,26?,27?,31-,32+/m1/s1
SMILES	CC(=CCc1c(cc(c2c(=O)c(c(c3ccc(cc3)O)oc12)O[C@H]1C(C([C@@H](C(CO)O1)O)O)O)O)O[C@H]1C([C@H]([C@@H](C(CO)O1)O)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	678.22	Volume:	636.161 ? Van der Waals volume.
Dense:	1.066	LogP:	0.991 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.825 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.524 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	31.0
TPSA:	269.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.118	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.965	Fsp³:	0.469
MCE-18:	123.319 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.663	Fluc inhibitor:	0.203 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.816 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.974 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.071	Promiscuous compounds:	0.062

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.445	MDCK Permeability:	-5.053
Pgp-inhibitor:	0.0	Pgp-substrate:	0.972
PAMPA:	1.0 ? 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):	0.989
20% Bioavailability (F20%):	0.976	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.4
Plasma Protein Binding (PPB):	78.6%	Volume Distribution (VD):	0.014
Fu:	22.157% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.834
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.261
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.368
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.98 ? 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):

1.967

Half-life (T1/2):

4.72

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.149
Human Hepatotoxicity (H-HT):	0.593	Drug-induced Liver Injury (DILI):	0.677
AMES Toxicity:	0.635	Rat Oral Acute Toxicity:	0.144
Maximum Recommended Daily Dose:	0.064	Skin Sensitization:	0.937
Carcinogencity:	0.053	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.997
Hematotoxicity:	0.034	Drug-induced Nephrotoxicity:	0.298
Genotoxicity:	0.7	RPMI-8226 Immunitoxicity:	0.059
A549 Cytotoxicity:	0.132	Hek293 Cytotoxicity:	0.662
BCF:	0.689 ? 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:	3.423 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.38 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.247 ? 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
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12081149]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	root	n.a.	PMID[22051934]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24066589]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	aerial parts	herbal garden of Chungbuk National University, Cheongju, Korea	2012-Oct	PMID[24963714]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8699184]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	aerial part	n.a.	Database[Article]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1689	Epimedium pubescens	Species	Berberidaceae	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]
NPO1689	Epimedium pubescens	Species	Berberidaceae	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]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	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 NPC258552 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	13836
0.1-0.2	31067
0.2-0.3	3724
0.3-0.4	864
0.4-0.5	275
0.5-0.6	71
0.6-0.7	15
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.814	Intermediate Similarity	NPC5319
0.6782	Remote Similarity	NPC66087
0.6703	Remote Similarity	NPC131745
0.6667	Remote Similarity	NPC297987
0.6477	Remote Similarity	NPC116458
0.6477	Remote Similarity	NPC246943
0.6413	Remote Similarity	NPC183672
0.6353	Remote Similarity	NPC77672
0.6353	Remote Similarity	NPC133671
0.6353	Remote Similarity	NPC135391
0.6353	Remote Similarity	NPC78263
0.6353	Remote Similarity	NPC250069
0.6279	Remote Similarity	NPC8573
0.6023	Remote Similarity	NPC24043
0.6023	Remote Similarity	NPC488080
0.6023	Remote Similarity	NPC169977
0.5909	Remote Similarity	NPC136042
0.5889	Remote Similarity	NPC168584
0.5795	Remote Similarity	NPC289667
0.5795	Remote Similarity	NPC249281
0.5773	Remote Similarity	NPC64425
0.5761	Remote Similarity	NPC605784
0.5745	Remote Similarity	NPC278419
0.5745	Remote Similarity	NPC179198
0.573	Remote Similarity	NPC145038
0.573	Remote Similarity	NPC56077
0.573	Remote Similarity	NPC281131
0.573	Remote Similarity	NPC253662
0.573	Remote Similarity	NPC179950
0.573	Remote Similarity	NPC88789
0.573	Remote Similarity	NPC491374
0.5667	Remote Similarity	NPC46420
0.5632	Remote Similarity	NPC288084
0.5607	Remote Similarity	NPC483158
0.5607	Remote Similarity	NPC483157
0.5556	Remote Similarity	NPC64305
0.5521	Remote Similarity	NPC480466
0.5521	Remote Similarity	NPC139320
0.5506	Remote Similarity	NPC111929
0.5506	Remote Similarity	NPC320283
0.5506	Remote Similarity	NPC41121
0.55	Remote Similarity	NPC35119
0.5495	Remote Similarity	NPC84362
0.5472	Remote Similarity	NPC164704
0.5444	Remote Similarity	NPC39360
0.5444	Remote Similarity	NPC29763
0.5444	Remote Similarity	NPC210003
0.5435	Remote Similarity	NPC472459
0.5435	Remote Similarity	NPC599850
0.5385	Remote Similarity	NPC323593
0.5385	Remote Similarity	NPC203500
0.5376	Remote Similarity	NPC488071
0.5368	Remote Similarity	NPC203050
0.5368	Remote Similarity	NPC225434
0.5368	Remote Similarity	NPC276377
0.5347	Remote Similarity	NPC32641
0.5347	Remote Similarity	NPC256188
0.5275	Remote Similarity	NPC19388
0.5275	Remote Similarity	NPC240431
0.5275	Remote Similarity	NPC55786
0.5269	Remote Similarity	NPC42773
0.5269	Remote Similarity	NPC45522
0.5258	Remote Similarity	NPC251417
0.5253	Remote Similarity	NPC150164
0.5229	Remote Similarity	NPC470716
0.5213	Remote Similarity	NPC60735
0.5213	Remote Similarity	NPC26230
0.5208	Remote Similarity	NPC488072
0.5185	Remote Similarity	NPC470715
0.5185	Remote Similarity	NPC25523
0.5181	Remote Similarity	NPC97326
0.5158	Remote Similarity	NPC101026
0.5158	Remote Similarity	NPC148710
0.5158	Remote Similarity	NPC120099
0.5158	Remote Similarity	NPC488077
0.5133	Remote Similarity	NPC470720
0.5109	Remote Similarity	NPC83283
0.5106	Remote Similarity	NPC59534
0.5106	Remote Similarity	NPC325555
0.5106	Remote Similarity	NPC226304
0.5102	Remote Similarity	NPC480463
0.5055	Remote Similarity	NPC67037
0.5055	Remote Similarity	NPC255615
0.5052	Remote Similarity	NPC170052
0.5052	Remote Similarity	NPC135846
0.505	Remote Similarity	NPC186816
0.5044	Remote Similarity	NPC470717

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC258552 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3975
0.1-0.2	5090
0.2-0.3	72
0.3-0.4	8
0.4-0.5	4
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.814	Intermediate Similarity	NPD7804	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