NPASS Compound

Natural Product: NPC241846

Natural Product ID	NPC241846
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	1-(1,3-Benzodioxol-5-Yl)-2-[4-[(2S,3R,4R,5S)-5-[4-[1-(3,4-Dimethoxyphenyl)-1-Hydroxypropan-2-Yl]Oxy-3-Methoxyphenyl]-3,4-Dimethyloxolan-2-Yl]-2-Methoxyphenoxy]Propan-1-Ol
IUPAC Name	1-(1,3-benzodioxol-5-yl)-2-[4-[(2S,3R,4R,5S)-5-[4-[1-(3,4-dimethoxyphenyl)-1-hydroxypropan-2-yl]oxy-3-methoxyphenyl]-3,4-dimethyloxolan-2-yl]-2-methoxyphenoxy]propan-1-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL321124
PubChem CID	44336028
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 100105 0 0 0 0 0 0 0 0999 V2000 0.3411 -1.0475 -2.8189 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2660 -1.5248 -1.7244 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1228 -3.0057 -1.4696 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6823 -3.9006 -2.4750 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5806 -3.1011 -0.0648 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9609 -2.7543 0.2480 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2214 -2.3854 1.5700 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4945 -2.0541 1.9671 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5793 -2.0662 1.0921 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3340 -2.4262 -0.2086 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0408 -2.7574 -0.5903 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3155 -2.4801 -1.1764 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9903 -2.8589 -2.4893 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7874 -1.7361 1.5487 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0499 -1.6079 1.0449 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9234 -2.8392 1.3830 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8320 -0.4371 1.5937 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2476 0.8559 1.2013 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6567 2.0403 1.8065 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1193 3.2360 1.4387 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1491 3.3118 0.4517 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7456 2.1391 -0.1462 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2900 0.9160 0.2242 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7868 2.4806 -1.0812 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2592 3.7339 -0.7010 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4218 4.3471 -0.1355 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9711 -0.5437 2.9868 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7977 -2.0952 0.5091 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8566 -1.0014 -0.3650 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3815 -0.2271 -0.3602 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3379 1.1479 -0.3517 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4727 1.9164 -0.3290 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7620 1.3087 -0.3128 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8095 -0.0565 -0.3220 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6283 -0.7848 -0.3454 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0335 -0.7548 -0.3086 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0859 -2.1558 -0.3183 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8517 2.1228 -0.2885 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1883 1.8705 -0.2565 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8181 2.5370 -1.4792 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8599 2.4135 1.0124 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3096 2.0785 1.0372 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6926 0.7798 1.3346 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0337 0.4742 1.3664 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9924 1.4254 1.1101 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6045 2.6985 0.8185 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2637 3.0382 0.7786 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5510 3.6610 0.5601 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2993 5.0009 0.2493 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3548 1.0955 1.1472 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.7205 -0.2511 1.4579 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2590 1.8366 2.1441 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5459 -1.7266 -2.8664 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8339 -1.1258 -3.8114 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0375 0.0126 -2.7038 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2980 -1.2502 -2.0043 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0025 -3.1591 -1.4205 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8557 -4.4385 -3.0370 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2427 -3.4030 -3.3220 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2726 -4.7669 -2.0525 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2704 -4.0725 0.4180 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4192 -2.3558 2.3031 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6448 -1.7707 3.0200 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8550 -3.0358 -1.6039 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1853 -2.2484 -2.9346 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6091 -3.9091 -2.4438 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8957 -2.9022 -3.1307 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0478 -1.5998 -0.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2809 -2.6649 2.4183 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2932 -3.7435 1.3950 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7946 -2.8881 0.7267 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8890 -0.4498 1.1937 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4066 1.9963 2.5715 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4137 4.1926 1.8905 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9139 0.0509 -0.3029 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8751 4.3056 -1.5597 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4833 3.5341 0.0794 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2469 -1.1087 3.3591 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7101 -0.3869 -0.0006 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6125 1.6958 -0.3634 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4523 3.0119 -0.3223 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7343 -1.8655 -0.3521 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1314 -2.4881 -0.5253 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8306 -2.5423 0.7080 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4663 -2.6237 -1.1100 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4569 0.8223 -0.2902 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7434 2.0381 -1.7928 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0525 3.5978 -1.2663 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0594 2.5105 -2.2804 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6654 3.4913 1.0498 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9957 -0.0161 1.5461 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3860 -0.5303 1.5952 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0234 4.0631 0.5417 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2067 5.4105 -0.2380 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4848 5.0608 -0.5239 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9483 5.5951 1.1079 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2045 -0.9770 0.7893 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8055 -0.4100 1.3316 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4332 -0.5048 2.5167 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2716 1.9616 2.1238 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 3 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 9 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 25 26 1 0 17 27 1 0 5 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 1 0 33 38 1 0 38 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 46 48 1 0 48 49 1 0 45 50 1 0 50 51 1 0 41 52 1 0 29 2 1 0 35 30 1 0 47 42 1 0 11 6 1 0 23 18 1 0 26 21 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 6 3 57 1 1 4 58 1 0 4 59 1 0 4 60 1 0 5 61 1 1 7 62 1 0 8 63 1 0 11 64 1 0 13 65 1 0 13 66 1 0 13 67 1 0 15 68 1 0 16 69 1 0 16 70 1 0 16 71 1 0 17 72 1 0 19 73 1 0 20 74 1 0 23 75 1 0 25 76 1 0 25 77 1 0 27 78 1 0 29 79 1 1 31 80 1 0 32 81 1 0 35 82 1 0 37 83 1 0 37 84 1 0 37 85 1 0 39 86 1 0 40 87 1 0 40 88 1 0 40 89 1 0 41 90 1 0 43 91 1 0 44 92 1 0 47 93 1 0 49 94 1 0 49 95 1 0 49 96 1 0 51 97 1 0 51 98 1 0 51 99 1 0 52100 1 0 M END

Standard InCHIKey	GSWZMFDCPMPHDL-BNOKCTPTSA-N
Standard InCHI	InChI=1S/C41H48O11/c1-22-23(2)41(29-12-16-33(36(20-29)47-8)51-25(4)39(43)27-10-14-31-37(18-27)49-21-48-31)52-40(22)28-11-15-32(35(19-28)46-7)50-24(3)38(42)26-9-13-30(44-5)34(17-26)45-6/h9-20,22-25,38-43H,21H2,1-8H3/t22-,23-,24?,25?,38?,39?,40+,41+/m1/s1
SMILES	C[C@@H]1[C@@H](C)[C@@H](c2ccc(c(c2)OC)OC(C)C(c2ccc3c(c2)OCO3)O)O[C@@H]1c1ccc(c(c1)OC)OC(C)C(c1ccc(c(c1)OC)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	716.32	Volume:	731.408 ? Van der Waals volume.
Dense:	0.979	LogP:	3.263 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.247 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.676 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	33.0
TPSA:	123.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.135	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.61	Fsp³:	0.415
MCE-18:	120.552 ? 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:	0.876	Fluc inhibitor:	0.372 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.246 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.076	Promiscuous compounds:	0.02

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.858	MDCK Permeability:	-4.756
Pgp-inhibitor:	0.003	Pgp-substrate:	0.02
PAMPA:	0.045 ? 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%):	0.005	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.992
Plasma Protein Binding (PPB):	93.8%	Volume Distribution (VD):	0.495
Fu:	6.282% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.897
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.066
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.999	CYP1A2-substrate:	0.632
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.983
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	0.305	CYP2D6-substrate:	0.854
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.96
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.961
HLM stability:	0.115 ? 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):

6.853

Half-life (T1/2):

2.308

ADMET: Toxicity

hERG Blockers:	0.39	hERG Blockers (10um):	0.641
Human Hepatotoxicity (H-HT):	0.514	Drug-induced Liver Injury (DILI):	0.739
AMES Toxicity:	0.283	Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.842	Skin Sensitization:	0.0
Carcinogencity:	0.871	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.615
Drug-induced Neurotoxicity:	0.577	Ototoxicity:	0.964
Hematotoxicity:	0.125	Drug-induced Nephrotoxicity:	0.917
Genotoxicity:	0.521	RPMI-8226 Immunitoxicity:	0.232
A549 Cytotoxicity:	0.074	Hek293 Cytotoxicity:	0.694
BCF:	1.599 ? 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:	4.056 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.246 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.207 ? 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
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.5897/AJB11.1524]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
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]
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]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29099182]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32456033]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31142	Saururus sp	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1436	Houttuynia cordata	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]
NPO26318	Saururus sp.	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1436	Houttuynia cordata	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]
NPO1436	Houttuynia cordata	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]

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	2
Inhibition	1

Activity Type	# Activity
Individual protein	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1214	Individual protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	IC50	=	82000.0	nM	PMID[15603959]
NPT2584	Individual protein	Acyl coenzyme A:cholesterol acyltransferase 2	Homo sapiens	Inhibition	=	32.0	%	PMID[15149654]

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 NPC241846 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	17000
0.1-0.2	30463
0.2-0.3	2034
0.3-0.4	242
0.4-0.5	69
0.5-0.6	27
0.6-0.7	7
0.7-0.8	0
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC302506
1.0	High Similarity	NPC93610
0.9808	High Similarity	NPC179521
0.8654	High Similarity	NPC260842
0.8654	High Similarity	NPC93783
0.8654	High Similarity	NPC320380
0.8361	Intermediate Similarity	NPC226153
0.8226	Intermediate Similarity	NPC304048
0.7258	Intermediate Similarity	NPC470372
0.7115	Intermediate Similarity	NPC57119
0.7115	Intermediate Similarity	NPC158471
0.7115	Intermediate Similarity	NPC226862
0.6667	Remote Similarity	NPC100425
0.6562	Remote Similarity	NPC77861
0.6346	Remote Similarity	NPC271208
0.6346	Remote Similarity	NPC233224
0.6346	Remote Similarity	NPC610263
0.614	Remote Similarity	NPC136750
0.614	Remote Similarity	NPC266848
0.5902	Remote Similarity	NPC135777
0.5862	Remote Similarity	NPC487685
0.5806	Remote Similarity	NPC142547
0.5806	Remote Similarity	NPC228469
0.5806	Remote Similarity	NPC488984
0.5806	Remote Similarity	NPC488985
0.5797	Remote Similarity	NPC99183
0.5769	Remote Similarity	NPC216929
0.5769	Remote Similarity	NPC312713
0.5769	Remote Similarity	NPC126935
0.5769	Remote Similarity	NPC65933
0.5769	Remote Similarity	NPC57268
0.5769	Remote Similarity	NPC172676
0.5645	Remote Similarity	NPC7744
0.5625	Remote Similarity	NPC484134
0.55	Remote Similarity	NPC473090
0.5357	Remote Similarity	NPC50683
0.5357	Remote Similarity	NPC112571
0.5357	Remote Similarity	NPC285725
0.5246	Remote Similarity	NPC94276
0.5246	Remote Similarity	NPC109822
0.5246	Remote Similarity	NPC605984
0.5167	Remote Similarity	NPC227160
0.5167	Remote Similarity	NPC82111
0.5167	Remote Similarity	NPC158331
0.5167	Remote Similarity	NPC483654
0.5082	Remote Similarity	NPC487684

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC241846 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4095
0.1-0.2	4873
0.2-0.3	174
0.3-0.4	8
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