NPASS Compound

Natural Product: NPC26782

Natural Product ID	NPC26782
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NGMYNFJANBHLKA-NXIKOVSOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44259054
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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 67 70 0 0 0 0 0 0 0 0999 V2000 -6.7405 -0.1899 1.4040 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5173 -0.6780 0.6130 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1428 0.0766 -0.3672 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0575 -0.0279 -1.3379 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2175 -1.2047 -1.2150 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6475 -2.4511 -1.6489 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8225 -3.5461 -1.5478 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5558 -3.4297 -1.0155 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1448 -2.1723 -0.5870 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1071 -1.9875 -0.0498 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8586 -2.9818 0.0416 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5522 -0.7356 0.3891 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3017 0.3114 0.2719 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0139 1.6797 0.6813 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8440 2.7174 0.2522 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6804 4.0246 0.6317 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3405 4.3866 1.4788 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1666 3.3888 1.9133 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9957 2.0574 1.5243 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4802 5.7124 1.8431 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4106 6.6936 1.3566 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5150 0.1086 -0.2563 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9413 -1.0512 -0.6711 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8291 -0.6353 0.9102 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9239 -0.4625 0.0200 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9700 0.5100 0.4355 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9229 0.6071 -0.7758 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4052 -0.7130 -1.2273 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5133 -1.8728 -0.9520 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4180 -3.0347 -0.5095 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5815 -1.7100 0.0158 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6981 -0.9105 -0.7316 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9496 1.5074 -0.4865 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7318 -0.0952 1.4374 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6915 -4.5098 -0.8956 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9427 -2.5264 -2.1840 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9384 -1.9480 1.0869 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0534 0.7922 1.0611 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4275 -0.2078 2.4711 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5245 -0.9509 1.2141 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7649 1.0137 -0.5268 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4963 -0.0497 -2.3772 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4341 0.9092 -1.2962 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1705 -4.5120 -1.8899 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6546 2.4281 -0.4237 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3855 4.7384 0.2346 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9754 3.6560 2.5804 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6707 1.3251 1.9287 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4667 6.3548 1.5387 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3027 7.6429 1.8974 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2278 6.8712 0.2880 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5634 -0.2165 -0.9938 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6491 1.5170 0.6924 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3036 1.0971 -1.5743 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5326 -0.6557 -2.3499 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0082 -2.2428 -1.8739 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2207 -2.6193 0.1591 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8245 -3.7186 0.1571 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7999 -3.6121 -1.3488 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1208 -1.5869 -1.3511 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7702 1.3136 -1.0040 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4780 0.2626 2.3424 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7003 -5.1669 -0.1342 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1228 -2.3525 -3.1607 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3759 -2.8426 0.5612 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2844 -2.1234 2.1591 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8438 -1.9721 1.1711 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 20 21 1 0 13 22 1 0 22 23 1 0 12 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 29 31 1 0 28 32 1 0 27 33 1 0 26 34 1 0 8 35 1 0 6 36 1 0 2 37 1 0 23 5 1 0 31 25 1 0 23 9 2 0 19 14 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 7 44 1 0 15 45 1 0 16 46 1 0 18 47 1 0 19 48 1 0 21 49 1 0 21 50 1 0 21 51 1 0 25 52 1 6 26 53 1 1 27 54 1 0 28 55 1 6 29 56 1 0 30 57 1 0 30 58 1 0 30 59 1 0 32 60 1 0 33 61 1 0 34 62 1 0 35 63 1 0 36 64 1 0 37 65 1 0 37 66 1 0 37 67 1 0 M END

Standard InCHIKey	NGMYNFJANBHLKA-NXIKOVSOSA-N
Standard InCHI	InChI=1S/C27H30O10/c1-12(2)5-10-16-17(28)11-18(29)19-21(31)26(37-27-23(33)22(32)20(30)13(3)35-27)24(36-25(16)19)14-6-8-15(34-4)9-7-14/h5-9,11,13,20,22-23,27-30,32-33H,10H2,1-4H3/t13?,20-,22?,23-,27-/m0/s1
SMILES	CC(=CCc1c(cc(c2c(=O)c(c(c3ccc(cc3)OC)oc12)O[C@H]1[C@H](C([C@H](C(C)O1)O)O)O)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	514.18	Volume:	505.496 ? Van der Waals volume.
Dense:	1.017	LogP:	3.376 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.979 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.514 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	25.0
TPSA:	159.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.31	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.143	Fsp³:	0.37
MCE-18:	91.568 ? 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:	0.692	Fluc inhibitor:	0.249 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.977 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.978 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.04	Promiscuous compounds:	0.099

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.865	MDCK Permeability:	-5.135
Pgp-inhibitor:	0.087	Pgp-substrate:	0.889
PAMPA:	0.96 ? 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):	0.575
20% Bioavailability (F20%):	0.73	30% Bioavailability (F30%):	0.961
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.83
Plasma Protein Binding (PPB):	91.941%	Volume Distribution (VD):	0.17
Fu:	7.726% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.953
OATP1B3 inhibitor:	0.984	BCRP inhibitor:	0.938
BSEP inhibitor:	0.471

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.859
CYP2C19-inhibitor:	0.041	CYP2C19-substrate:	0.935
CYP2C9-inhibitor:	0.036	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.003	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

2.284

Half-life (T1/2):

2.158

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.349
Human Hepatotoxicity (H-HT):	0.727	Drug-induced Liver Injury (DILI):	0.992
AMES Toxicity:	0.955	Rat Oral Acute Toxicity:	0.487
Maximum Recommended Daily Dose:	0.269	Skin Sensitization:	0.997
Carcinogencity:	0.231	Eye Corrosion:	0.0
Eye Irritation:	0.159	Respiratory Toxicity:	0.836
Drug-induced Neurotoxicity:	0.198	Ototoxicity:	0.611
Hematotoxicity:	0.28	Drug-induced Nephrotoxicity:	0.694
Genotoxicity:	0.984	RPMI-8226 Immunitoxicity:	0.185
A549 Cytotoxicity:	0.817	Hek293 Cytotoxicity:	0.762
BCF:	1.535 ? 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:	4.267 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.72 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.183 ? 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]
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]
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]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[8482946]
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]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23024	Epimedium koreanum	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]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19403	Epimedium grandiflorum	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]
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]
NPO9141	Epimedium wushanense	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]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19403	Epimedium grandiflorum	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]
NPO23024	Epimedium koreanum	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]
NPO9141	Epimedium wushanense	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]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10969	Epimedium sagittatum	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]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	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]
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]
NPO9141	Epimedium wushanense	Species	Berberidaceae	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]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1689	Epimedium pubescens	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]
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]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13384	Epimedium sempervirens	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]

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 NPC26782 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	10870
0.1-0.2	33996
0.2-0.3	4008
0.3-0.4	656
0.4-0.5	281
0.5-0.6	41
0.6-0.7	1
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC278419
1.0	High Similarity	NPC179198
0.8462	Intermediate Similarity	NPC66087
0.7303	Intermediate Similarity	NPC5319
0.6023	Remote Similarity	NPC219904
0.5909	Remote Similarity	NPC472459
0.5843	Remote Similarity	NPC611303
0.5814	Remote Similarity	NPC111929
0.5814	Remote Similarity	NPC320283
0.5814	Remote Similarity	NPC41121
0.5795	Remote Similarity	NPC46420
0.5682	Remote Similarity	NPC265530
0.5679	Remote Similarity	NPC273538
0.5618	Remote Similarity	NPC271692
0.5568	Remote Similarity	NPC127546
0.5568	Remote Similarity	NPC249281
0.5568	Remote Similarity	NPC57625
0.5568	Remote Similarity	NPC173637
0.5568	Remote Similarity	NPC317489
0.5568	Remote Similarity	NPC223424
0.5568	Remote Similarity	NPC600591
0.5556	Remote Similarity	NPC59534
0.5543	Remote Similarity	NPC223747
0.5506	Remote Similarity	NPC64305
0.5506	Remote Similarity	NPC158674
0.5464	Remote Similarity	NPC131745
0.5455	Remote Similarity	NPC135599
0.5455	Remote Similarity	NPC73855
0.5455	Remote Similarity	NPC113968
0.5455	Remote Similarity	NPC328940
0.5455	Remote Similarity	NPC277174
0.5455	Remote Similarity	NPC606877
0.5444	Remote Similarity	NPC349108
0.5275	Remote Similarity	NPC305811
0.5275	Remote Similarity	NPC27640
0.5263	Remote Similarity	NPC265115
0.5222	Remote Similarity	NPC289667
0.5213	Remote Similarity	NPC116458
0.5213	Remote Similarity	NPC246943
0.5208	Remote Similarity	NPC251417
0.5158	Remote Similarity	NPC276377
0.5158	Remote Similarity	NPC355481
0.5149	Remote Similarity	NPC473327
0.5149	Remote Similarity	NPC606657
0.5106	Remote Similarity	NPC120099
0.5053	Remote Similarity	NPC605784

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC26782 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3209
0.1-0.2	5844
0.2-0.3	89
0.3-0.4	2
0.4-0.5	4
0.5-0.6	1
0.6-0.7	0
0.7-0.8	1
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
0.7303	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD4378	Phase 3

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