NPASS Compound

Natural Product: NPC320380

Natural Product ID	NPC320380
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZGXXNVOBEIRACL-VOGCUZRYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	15605952
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003423] 7,7'-epoxylignans

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 105109 0 0 0 0 0 0 0 0999 V2000 -2.3946 -3.6150 -0.1684 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4206 -2.4959 -0.3339 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0249 -2.9866 -0.6542 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5036 -1.9239 -1.5491 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4890 -0.9495 -1.6587 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7079 -1.6208 -1.5530 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7811 -0.6513 -1.2789 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6305 0.2510 -0.2518 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6203 1.1651 -0.0100 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8074 1.2332 -0.7719 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9367 0.2979 -1.8178 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9335 -0.5932 -2.0254 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7303 2.1132 -0.5223 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7114 2.9376 -0.3745 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2373 4.4033 -0.4623 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4700 2.8815 0.9595 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1542 1.5859 1.1231 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2454 1.2777 0.3614 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8478 0.0692 0.5373 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3993 -0.8640 1.4596 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3052 -0.5402 2.2155 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6776 0.6884 2.0496 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0435 -2.0727 1.5984 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6675 -3.0684 2.5001 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9513 -0.2568 -0.2246 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.4885 0.6368 -1.1993 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4469 3.8581 0.9043 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4453 2.0725 1.0416 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2669 2.0130 1.8103 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7910 -1.3342 -1.1597 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9408 -1.7161 -1.8006 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1650 -1.1547 -1.4572 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2318 -0.2003 -0.4600 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0632 0.1572 0.1602 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8546 -0.3914 -0.1728 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4539 0.3288 -0.1545 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7550 1.3026 0.7942 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3643 2.4795 0.0493 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7642 0.7251 1.7715 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0526 0.4600 1.1044 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1050 1.3360 1.2596 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3220 1.1024 0.6433 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5172 -0.0186 -0.1471 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4772 -0.8899 -0.3044 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2761 -0.6485 0.3107 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7523 -0.2138 -0.7453 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0339 -1.3319 -1.5652 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3938 1.9823 0.7924 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1925 3.1264 1.5989 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1983 -0.3798 2.3684 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3166 -1.5394 -2.1019 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2701 -2.5068 -3.1176 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7944 -3.2244 0.5869 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2049 -3.2679 0.5185 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8598 -3.9796 -1.0945 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8579 -4.4278 0.3893 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4383 -1.8818 0.5895 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1776 -3.9589 -1.2082 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5996 -2.3565 -2.5834 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8742 -2.2668 -2.4243 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7336 0.2415 0.3660 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8531 0.3258 -2.4284 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0683 -1.3115 -2.8509 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4837 2.8913 -1.2096 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6821 4.6531 0.4537 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6926 4.5682 -1.3990 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1894 5.0048 -0.4421 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7439 3.1286 1.7446 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5801 2.0117 -0.3495 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9347 -1.2524 2.9444 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8179 0.8924 2.6722 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1403 -4.0540 2.2375 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9363 -2.8771 3.5505 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5527 -3.1640 2.4621 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5290 0.3684 -1.4509 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5328 1.6871 -0.8189 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8211 0.5861 -2.0727 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7372 4.1895 1.7708 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3413 2.0846 1.1875 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2316 2.8489 2.5340 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1654 1.0446 2.3711 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9723 -2.4603 -2.5947 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1047 0.9149 0.9552 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9874 -0.0546 0.3627 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9242 1.6984 1.3748 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3315 2.1564 -0.3683 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4697 3.2983 0.7653 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6350 2.7885 -0.7156 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8903 1.4863 2.5723 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0286 2.2432 1.8675 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5994 -1.7632 -0.9096 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4547 -1.3413 0.1829 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5539 -2.2592 -1.2123 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1302 -1.4976 -1.5193 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7713 -1.1216 -2.6178 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9048 2.8039 2.6344 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1078 3.7416 1.6280 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3056 3.7119 1.2329 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9234 -1.0789 1.7458 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8015 -3.4156 -2.7102 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2836 -2.7161 -3.5033 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6002 -2.1106 -3.9164 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7560 -4.3231 0.8305 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8821 -3.0116 0.4324 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4078 -2.7151 1.4883 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 10 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 20 23 1 0 23 24 1 0 19 25 1 0 25 26 1 0 16 27 1 0 9 28 1 0 28 29 1 0 4 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 33 36 1 0 36 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 43 46 1 0 46 47 1 0 42 48 1 0 48 49 1 0 39 50 1 0 32 51 1 0 51 52 1 0 3 53 1 0 6 2 1 0 12 7 1 0 22 17 1 0 35 30 1 0 45 40 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 0 3 58 1 0 4 59 1 0 6 60 1 0 8 61 1 0 11 62 1 0 12 63 1 0 14 64 1 0 15 65 1 0 15 66 1 0 15 67 1 0 16 68 1 0 18 69 1 0 21 70 1 0 22 71 1 0 24 72 1 0 24 73 1 0 24 74 1 0 26 75 1 0 26 76 1 0 26 77 1 0 27 78 1 0 29 79 1 0 29 80 1 0 29 81 1 0 31 82 1 0 34 83 1 0 35 84 1 0 37 85 1 0 38 86 1 0 38 87 1 0 38 88 1 0 39 89 1 0 41 90 1 0 44 91 1 0 45 92 1 0 47 93 1 0 47 94 1 0 47 95 1 0 49 96 1 0 49 97 1 0 49 98 1 0 50 99 1 0 52100 1 0 52101 1 0 52102 1 0 53103 1 0 53104 1 0 53105 1 0 M END

Standard InCHIKey	ZGXXNVOBEIRACL-VOGCUZRYSA-N
Standard InCHI	InChI=1S/C42H52O11/c1-23-24(2)42(30-14-18-34(38(22-30)50-10)52-26(4)40(44)28-12-16-32(46-6)36(20-28)48-8)53-41(23)29-13-17-33(37(21-29)49-9)51-25(3)39(43)27-11-15-31(45-5)35(19-27)47-7/h11-26,39-44H,1-10H3/t23-,24-,25-,26-,39+,40+,41+,42+/m1/s1
SMILES	CC1C(C(OC1C2=CC(=C(C=C2)OC(C)C(C3=CC(=C(C=C3)OC)OC)O)OC)C4=CC(=C(C=C4)OC(C)C(C5=CC(=C(C=C5)OC)OC)O)OC)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	732.35	Volume:	757.261 ? Van der Waals volume.
Dense:	0.967	LogP:	3.055 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.163 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.411 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	29.0
TPSA:	123.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.117	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.392	Fsp³:	0.429
MCE-18:	109.667 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.493	Fluc inhibitor:	0.183 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.197 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.263	Promiscuous compounds:	0.18

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.881	MDCK Permeability:	-4.747
Pgp-inhibitor:	0.044	Pgp-substrate:	0.069
PAMPA:	0.0 ? 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):	0.001
20% Bioavailability (F20%):	0.005	30% Bioavailability (F30%):	0.012
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	90.539%	Volume Distribution (VD):	0.367
Fu:	10.46% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.962
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.676
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.674	CYP1A2-substrate:	0.879
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.739
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.516
CYP2D6-inhibitor:	0.131	CYP2D6-substrate:	0.343
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	0.902
HLM stability:	0.47 ? 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):

8.856

Half-life (T1/2):

2.794

ADMET: Toxicity

hERG Blockers:	0.517	hERG Blockers (10um):	0.801
Human Hepatotoxicity (H-HT):	0.389	Drug-induced Liver Injury (DILI):	0.549
AMES Toxicity:	0.154	Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.936	Skin Sensitization:	0.0
Carcinogencity:	0.734	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.783
Drug-induced Neurotoxicity:	0.906	Ototoxicity:	0.988
Hematotoxicity:	0.086	Drug-induced Nephrotoxicity:	0.915
Genotoxicity:	0.124	RPMI-8226 Immunitoxicity:	0.306
A549 Cytotoxicity:	0.054	Hek293 Cytotoxicity:	0.703
BCF:	1.526 ? 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:	4.03 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.063 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.98 ? 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
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)99818-1]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421725]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754613]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	root	n.a.	PMID[14750033]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165135]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15482936]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	roots	n.a.	n.a.	PMID[18841903]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24359277]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[24387347]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12012	Saururus cernuus	Species	Saururaceae	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	1

Activity Type	# Activity
Cell line	1

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
NPT396	Cell line	T47D	Homo sapiens	IC50	=	3.0	nM	PMID[36774697]

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 NPC320380 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	14904
0.1-0.2	32446
0.2-0.3	2236
0.3-0.4	175
0.4-0.5	52
0.5-0.6	18
0.6-0.7	11
0.7-0.8	0
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC260842
1.0	High Similarity	NPC93783
0.8654	High Similarity	NPC302506
0.8654	High Similarity	NPC241846
0.8654	High Similarity	NPC93610
0.8462	Intermediate Similarity	NPC179521
0.8182	Intermediate Similarity	NPC470372
0.7368	Intermediate Similarity	NPC77861
0.7213	Intermediate Similarity	NPC226153
0.7097	Intermediate Similarity	NPC304048
0.6667	Remote Similarity	NPC216929
0.6667	Remote Similarity	NPC312713
0.6667	Remote Similarity	NPC126935
0.6667	Remote Similarity	NPC65933
0.6667	Remote Similarity	NPC57268
0.6667	Remote Similarity	NPC172676
0.6452	Remote Similarity	NPC99183
0.6226	Remote Similarity	NPC473090
0.6122	Remote Similarity	NPC50683
0.6122	Remote Similarity	NPC112571
0.6122	Remote Similarity	NPC285725
0.5926	Remote Similarity	NPC94276
0.5926	Remote Similarity	NPC109822
0.5926	Remote Similarity	NPC605984
0.5849	Remote Similarity	NPC158331
0.5769	Remote Similarity	NPC57119
0.5769	Remote Similarity	NPC158471
0.5769	Remote Similarity	NPC226862
0.5741	Remote Similarity	NPC487684
0.5636	Remote Similarity	NPC11258
0.5636	Remote Similarity	NPC21867
0.5636	Remote Similarity	NPC45774
0.5636	Remote Similarity	NPC74914
0.55	Remote Similarity	NPC100425
0.5455	Remote Similarity	NPC136750
0.5455	Remote Similarity	NPC266848
0.5439	Remote Similarity	NPC190629
0.5263	Remote Similarity	NPC473091
0.5263	Remote Similarity	NPC470258

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC320380 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3551
0.1-0.2	5363
0.2-0.3	232
0.3-0.4	4
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