NPASS Compound

Natural Product: NPC112438

Natural Product ID	NPC112438
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BTSHIWNGQGFPHJ-XODVFGJGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11972471
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 108113 0 0 0 0 0 0 0 0999 V2000 -5.7281 3.2186 1.1349 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6621 3.4810 0.1293 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2280 2.4867 -0.6252 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7941 1.1696 -0.4677 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8851 0.0905 -0.0931 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5295 -1.1223 0.2965 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7270 -2.1715 0.6064 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3595 -2.1105 0.5604 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7453 -0.9387 0.1849 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3828 -0.8816 0.1364 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2883 -1.9052 0.4384 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2136 0.3164 -0.2497 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5492 1.3722 -0.5622 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0238 2.6436 -0.9680 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2719 2.8030 -1.5098 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8083 4.0481 -1.8282 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0326 5.1532 -1.5795 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2329 5.0588 -1.0352 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7007 3.8050 -0.7442 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5222 6.4309 -1.8817 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7610 7.5827 -1.6423 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8754 1.2669 -0.4986 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5207 0.1838 -0.1479 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6049 0.3144 -0.2737 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3924 0.6441 0.8455 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9780 -0.5994 1.4959 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4260 -0.3819 1.8665 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2330 0.0694 0.6644 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3010 0.7784 -0.2956 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0477 1.7528 -1.1741 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3954 1.5087 0.4630 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8541 -1.0110 0.1134 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2369 -0.9945 0.0723 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8524 -2.1045 0.8808 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3536 -1.9479 0.8618 C 0 0 1 0 0 0 0 0 0 0 0 0 9.7721 -1.6444 -0.5566 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6312 -1.9767 -1.4697 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0180 -1.8206 -2.9339 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5952 -1.0984 -1.2485 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9459 -2.3108 -0.9102 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7200 -0.8560 1.6584 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5222 -1.9369 2.2604 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5401 0.5099 2.9228 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2431 -0.8793 2.6238 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5562 -3.1956 0.8808 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9091 -1.1459 0.3307 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6966 -2.2357 0.6649 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5902 -2.0060 1.8723 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3697 -3.2800 2.1143 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1243 -4.3348 1.0907 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9340 -3.8494 -0.3031 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1564 -4.0568 -1.1707 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5719 -5.4036 -1.1073 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5710 -2.5092 -0.4050 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0721 -5.2085 1.4509 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7321 -3.0523 2.2902 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9045 -1.5567 2.9775 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1443 4.8530 -0.0214 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9263 4.1409 1.7357 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6437 2.8783 0.6267 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3715 2.3895 1.7830 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4629 2.7007 -1.3611 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6863 1.1550 0.2344 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1919 0.8755 -1.4989 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1505 -3.1140 0.9088 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9085 1.9585 -1.7419 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8089 4.1566 -2.2639 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8198 5.9543 -0.8518 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6622 3.6830 -0.2964 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3809 8.4549 -1.8439 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1486 7.5480 -2.2906 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4452 7.5861 -0.5615 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6909 1.1491 1.5635 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8803 -1.4297 0.7846 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8275 -1.3498 2.2078 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9701 0.8062 1.0130 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8104 0.0299 -0.9315 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5173 1.2473 -2.0449 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2988 2.4544 -1.5862 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7726 2.3727 -0.6023 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6692 -0.0441 0.4786 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5987 -3.1183 0.5546 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8704 -2.8775 1.1909 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9771 -0.5385 -0.6645 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3283 -3.0320 -1.2988 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1449 -1.6549 -3.5933 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5192 -2.7443 -3.3063 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6837 -0.9455 -3.0383 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6984 -1.8297 -0.5238 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1979 -1.2278 2.4429 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6444 -0.9631 2.4807 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1469 1.3832 2.7703 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1714 -0.1106 3.2504 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6335 -4.0582 0.3541 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1374 -3.1721 0.8602 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3263 -1.2248 1.5812 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9912 -3.6784 3.0993 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0392 -4.9981 1.0776 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1057 -4.4208 -0.7845 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9675 -3.3614 -0.8719 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9115 -3.8601 -2.2330 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8297 -5.9225 -1.5169 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1290 -5.5058 2.3744 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9298 -2.2147 2.7591 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2776 -2.2243 3.3413 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9601 5.6110 -0.0896 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4384 5.0791 0.8212 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5529 4.9916 -0.9623 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 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 37 39 1 0 36 40 1 0 35 41 1 0 34 42 1 0 27 43 1 0 26 44 1 0 8 45 1 0 6 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 51 54 1 0 50 55 1 0 49 56 1 0 48 57 1 0 2 58 1 0 23 5 1 0 31 25 1 0 39 33 1 0 54 47 1 0 23 9 2 0 19 14 1 0 1 59 1 0 1 60 1 0 1 61 1 0 3 62 1 0 4 63 1 0 4 64 1 0 7 65 1 0 15 66 1 0 16 67 1 0 18 68 1 0 19 69 1 0 21 70 1 0 21 71 1 0 21 72 1 0 25 73 1 1 26 74 1 6 27 75 1 1 28 76 1 1 29 77 1 6 30 78 1 0 30 79 1 0 30 80 1 0 33 81 1 1 34 82 1 6 35 83 1 1 36 84 1 1 37 85 1 6 38 86 1 0 38 87 1 0 38 88 1 0 40 89 1 0 41 90 1 0 42 91 1 0 43 92 1 0 44 93 1 0 45 94 1 0 47 95 1 1 48 96 1 6 49 97 1 1 50 98 1 6 51 99 1 6 52100 1 0 52101 1 0 53102 1 0 55103 1 0 56104 1 0 57105 1 0 58106 1 0 58107 1 0 58108 1 0 M END

Standard InCHIKey	BTSHIWNGQGFPHJ-XODVFGJGSA-N
Standard InCHI	InChI=1S/C39H50O19/c1-14(2)6-11-19-21(54-39-31(49)28(46)25(43)22(13-40)55-39)12-20(41)23-26(44)36(34(56-35(19)23)17-7-9-18(51-5)10-8-17)58-38-32(50)29(47)33(16(4)53-38)57-37-30(48)27(45)24(42)15(3)52-37/h6-10,12,15-16,22,24-25,27-33,37-43,45-50H,11,13H2,1-5H3/t15-,16-,22+,24-,25+,27+,28-,29-,30+,31+,32+,33-,37-,38-,39+/m0/s1
SMILES	CC(=CCc1c(cc(c2c(=O)c(c(c3ccc(cc3)OC)oc12)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	822.29	Volume:	775.047 ? Van der Waals volume.
Dense:	1.061	LogP:	1.695 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.302 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.938 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	37.0
TPSA:	297.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	10.0	Rings:	6.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.103	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.537	Fsp³:	0.564
MCE-18:	153.639 ? 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:	0.687	Fluc inhibitor:	0.299 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.69 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.475 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.067	Promiscuous compounds:	0.16

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.381	MDCK Permeability:	-5.208
Pgp-inhibitor:	0.0	Pgp-substrate:	0.973
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):	0.894
20% Bioavailability (F20%):	0.125	30% Bioavailability (F30%):	0.986
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.024
Plasma Protein Binding (PPB):	77.782%	Volume Distribution (VD):	-0.114
Fu:	20.452% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.073
BSEP inhibitor:	0.008

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.596
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.893 ? 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):

1.075

Half-life (T1/2):

5.267

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.066
Human Hepatotoxicity (H-HT):	0.607	Drug-induced Liver Injury (DILI):	0.987
AMES Toxicity:	0.946	Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.002	Skin Sensitization:	0.999
Carcinogencity:	0.01	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.22	Drug-induced Nephrotoxicity:	0.898
Genotoxicity:	0.507	RPMI-8226 Immunitoxicity:	0.156
A549 Cytotoxicity:	0.309	Hek293 Cytotoxicity:	0.289
BCF:	0.716 ? 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:	3.549 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.451 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.504 ? 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
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26134	Epimedium davidii	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]
NPO26134	Epimedium davidii	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]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26134	Epimedium davidii	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]
NPO9141	Epimedium wushanense	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]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9141	Epimedium wushanense	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]

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 NPC112438 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	14996
0.1-0.2	29752
0.2-0.3	4152
0.3-0.4	704
0.4-0.5	233
0.5-0.6	17
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8602	High Similarity	NPC5319
0.6733	Remote Similarity	NPC131745
0.65	Remote Similarity	NPC278419
0.65	Remote Similarity	NPC179198
0.5524	Remote Similarity	NPC66087
0.5514	Remote Similarity	NPC139320
0.5446	Remote Similarity	NPC289667
0.5437	Remote Similarity	NPC472459
0.5333	Remote Similarity	NPC148710
0.5321	Remote Similarity	NPC471748
0.5283	Remote Similarity	NPC116458
0.5283	Remote Similarity	NPC246943
0.5278	Remote Similarity	NPC251417
0.5229	Remote Similarity	NPC480466
0.514	Remote Similarity	NPC605784
0.5138	Remote Similarity	NPC480463
0.5096	Remote Similarity	NPC64305
0.5088	Remote Similarity	NPC32641
0.5088	Remote Similarity	NPC256188
0.5088	Remote Similarity	NPC35119
0.5044	Remote Similarity	NPC240306

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC112438 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4167
0.1-0.2	4891
0.2-0.3	78
0.3-0.4	9
0.4-0.5	4
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8602	High 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