NPASS Compound

Natural Product: NPC24407

Natural Product ID	NPC24407
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-N-Pentadecylresorcinol
IUPAC Name	5-pentacosylbenzene-1,3-diol
Synonyms	5-N-Pentadecylresorcinol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1795559
PubChem CID	155463
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

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 89 89 0 0 0 0 0 0 0 0999 V2000 -11.8098 -0.9127 0.1312 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3489 -0.5531 -1.2647 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8517 -0.8642 -1.3846 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0860 -0.0608 -0.3805 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6080 -0.4001 -0.4488 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0737 -0.0891 -1.7988 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6320 -0.2930 -2.0103 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6973 0.6058 -1.3572 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7620 0.7236 0.1226 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5652 1.6356 0.5453 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5569 1.8229 2.0159 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3974 0.6196 2.8178 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2093 -0.1739 3.0081 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3251 -0.7152 1.9842 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4308 0.2612 1.2933 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4006 -0.4181 0.2150 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2635 0.6149 -0.4322 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2098 1.3142 0.4807 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1998 0.4436 1.1765 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1020 -0.3157 0.1906 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0401 -1.1406 1.0326 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9546 -1.9269 0.1655 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7822 -1.0171 -0.7053 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6833 -1.9157 -1.5354 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5776 -1.1231 -2.4670 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4376 -0.2137 -1.6671 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6833 -0.5773 -1.1860 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4605 0.2898 -0.4465 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7149 -0.0537 0.0472 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9389 1.5643 -0.1971 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6994 1.9496 -0.6663 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9427 1.0632 -1.4033 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1814 3.2266 -0.4142 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.5566 -0.1572 0.8744 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2767 -1.8752 0.3828 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9148 -1.1009 0.0464 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4531 0.5363 -1.4320 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9094 -1.1485 -1.9879 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5403 -0.5086 -2.4115 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6184 -1.9178 -1.2705 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4790 -0.1738 0.6529 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2454 1.0231 -0.6341 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0748 -0.0706 0.4277 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5433 -1.5702 -0.3765 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4026 0.9716 -2.0360 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6732 -0.7048 -2.5327 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4520 -0.3661 -3.1353 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3809 -1.3600 -1.6493 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6363 0.2494 -1.6084 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7115 1.6515 -1.8258 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6201 1.3940 0.4343 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6645 -0.1919 0.6841 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7196 1.2458 0.0366 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7941 2.6487 0.0783 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7865 2.6180 2.3158 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5228 2.3715 2.3112 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3012 -0.0833 2.6456 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6967 0.9636 3.9063 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5438 -1.0706 3.6851 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5285 0.3550 3.7804 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8409 -1.3920 1.2451 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6190 -1.4474 2.5040 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7890 1.2029 0.9711 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3409 0.5428 2.1233 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9679 -1.2762 0.6094 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2805 -0.8213 -0.5616 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8356 0.1983 -1.2878 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5768 1.3999 -0.8474 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8038 2.0248 -0.1658 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7214 1.9553 1.2328 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8139 1.0931 1.8325 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7510 -0.3225 1.8193 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5097 -1.0056 -0.4263 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6099 0.4017 -0.4770 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5780 -0.4234 1.7030 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3895 -1.8101 1.6524 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2982 -2.5343 -0.5261 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5743 -2.5826 0.8011 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3400 -0.2858 -0.1068 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1521 -0.4552 -1.4246 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0178 -2.5996 -2.0988 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2590 -2.5438 -0.8290 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2086 -1.8733 -2.9933 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9363 -0.5416 -3.1378 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0527 -1.5817 -1.4034 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4951 0.5494 -0.2514 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5505 2.2401 0.3821 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9846 1.3670 -1.7632 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8901 3.4214 0.5312 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 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 28 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 32 26 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 0 2 38 1 0 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 5 43 1 0 5 44 1 0 6 45 1 0 6 46 1 0 7 47 1 0 7 48 1 0 8 49 1 0 8 50 1 0 9 51 1 0 9 52 1 0 10 53 1 0 10 54 1 0 11 55 1 0 11 56 1 0 12 57 1 0 12 58 1 0 13 59 1 0 13 60 1 0 14 61 1 0 14 62 1 0 15 63 1 0 15 64 1 0 16 65 1 0 16 66 1 0 17 67 1 0 17 68 1 0 18 69 1 0 18 70 1 0 19 71 1 0 19 72 1 0 20 73 1 0 20 74 1 0 21 75 1 0 21 76 1 0 22 77 1 0 22 78 1 0 23 79 1 0 23 80 1 0 24 81 1 0 24 82 1 0 25 83 1 0 25 84 1 0 27 85 1 0 29 86 1 0 30 87 1 0 32 88 1 0 33 89 1 0 M END

Standard InCHIKey	GDJMJAKVVSGNLA-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C31H56O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-29-26-30(32)28-31(33)27-29/h26-28,32-33H,2-25H2,1H3
SMILES	CCCCCCCCCCCCCCCCCCCCCCCCCc1cc(O)cc(c1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	460.43	Volume:	545.847 ? Van der Waals volume.
Dense:	0.844	LogP:	9.574 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.89 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-8.326 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	24.0	Rigid Bonds:	6.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	1.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.151	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.005	Fsp³:	0.806
MCE-18:	6.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.782	Fluc inhibitor:	0.373 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.016 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.937	Promiscuous compounds:	0.111

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.219	MDCK Permeability:	-4.931
Pgp-inhibitor:	0.0	Pgp-substrate:	0.005
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):	0.567
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.966
Plasma Protein Binding (PPB):	104.07%	Volume Distribution (VD):	2.672
Fu:	0.126% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.776
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.991
BSEP inhibitor:	0.634

ADMET: Metabolism

CYP1A2-inhibitor:	0.156	CYP1A2-substrate:	0.998
CYP2C19-inhibitor:	0.339	CYP2C19-substrate:	0.975
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.999
CYP2D6-inhibitor:	0.999	CYP2D6-substrate:	0.951
CYP3A4-inhibitor:	0.004	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.898	CYP2C8-inhibitor:	1.0
HLM stability:	0.417 ? 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):

3.571

Half-life (T1/2):

4.192

ADMET: Toxicity

hERG Blockers:	0.925	hERG Blockers (10um):	0.977
Human Hepatotoxicity (H-HT):	0.523	Drug-induced Liver Injury (DILI):	0.058
AMES Toxicity:	0.021	Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.644	Skin Sensitization:	0.999
Carcinogencity:	0.14	Eye Corrosion:	0.955
Eye Irritation:	0.999	Respiratory Toxicity:	0.989
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.105
Hematotoxicity:	0.04	Drug-induced Nephrotoxicity:	0.045
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.992	Hek293 Cytotoxicity:	0.826
BCF:	0.409 ? 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:	5.66 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.787 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.609 ? 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
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Seeds	n.a.		DOI[10.1002/(SICI)1097-0010(199909)79:12<1620::AID-JSFA410>3.0.CO;2-G]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1007/s00217-002-0656-1]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1007/s00217-015-2561-4]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.		DOI[10.1016/j.foodchem.2007.07.014]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1016/j.foodchem.2010.05.061]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.		DOI[10.1016/j.foodchem.2010.05.061]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1016/j.indcrop.2013.08.051]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.		DOI[10.1016/j.ssnmr.2006.05.001]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1016/j.yclnex.2017.01.002; 10.31989/ffhd.v6i3.245]DOI[10.1016/j.yclnex.2017.01.002; 10.31989/ffhd.v6i3.245]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1080/09064710.2011.598543]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1111/j.1365-2621.1989.tb04709.x]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1111/j.1365-3040.1996.tb00393.x]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1111/j.1745-4530.2009.00507.x]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.15835/NBHA4017181]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.17221/540/2012-CJFS]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.2137/145960607781635822]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.2478/aoas-2014-0072]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.3136/NSKKK.48.606]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.3390/agriculture2030244]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10993146]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	Tsukuba, Japan	1998-JUN	PMID[12381108]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[15563205]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18270436]
NPO33268	wheat	n.a.	n.a.	n.a.	wheat germ	n.a.	n.a.	PMID[19284743]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21381697]
NPO33268	wheat	n.a.	n.a.	n.a.	wheat bran	n.a.	n.a.	PMID[21658963]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23793896]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24197199]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24254087]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[24967651]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[25026919]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[25977015]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[26351516]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[27556441]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	Schirgiswalde, Germany	2008-Oct	PMID[31206724]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	Schirgiswalde, Germany	2008-Aug	PMID[31206724]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	Cracow, Poland	2008-Sep	PMID[31206724]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	Schirgiswalde, Germany	2008-Sep	PMID[31206724]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[31619015]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38893452]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9134744]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Flowers	n.a.		PMID[9301422]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[9301422]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO709.1	Triticum durum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO33268	wheat	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO659	Secale cereale	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO709.1	Triticum durum	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8589	Triticum aestivum	Species	Poaceae	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
NPO22132	Hordeum vulgare	Dried Or Powder	n.a.	1.657176944	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO659	Secale cereale	Dried Or Powder	n.a.	0.445499976	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO659	Secale cereale	Dried Or Powder	n.a.	5.213964718	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO659	Secale cereale	n.a.	n.a.	0.44	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO659	Secale cereale	n.a.	n.a.	5.20817	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO709.1	Triticum durum	Dried Or Powder	n.a.	2.82659723	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO7269	Aronia melanocarpa	Ultrasonic extraction	Fruits	0.06 Â± 0.00	n.a.	n.a.	%	PMID[38893452]
NPO8589	Triticum aestivum	Dried Or Powder	n.a.	0.592460564	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO8589	Triticum aestivum	n.a.	n.a.	0.59014	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO8589	Triticum aestivum	n.a.	n.a.	2.82091	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]

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

Activity Type	# Activity
Cell line	2

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
NPT393	Cell line	HCT-116	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[20439614]
NPT139	Cell line	HT-29	Homo sapiens	IC50	>	50.0	ug.mL-1	PubChem BioAssay data set

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 NPC24407 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	28932
0.1-0.2	18811
0.2-0.3	1805
0.3-0.4	181
0.4-0.5	51
0.5-0.6	28
0.6-0.7	20
0.7-0.8	0
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC294186
1.0	High Similarity	NPC147310
1.0	High Similarity	NPC137415
1.0	High Similarity	NPC166313
1.0	High Similarity	NPC192032
1.0	High Similarity	NPC11280
0.8889	High Similarity	NPC246056
0.8182	Intermediate Similarity	NPC146798
0.8182	Intermediate Similarity	NPC222522
0.8182	Intermediate Similarity	NPC106396
0.8182	Intermediate Similarity	NPC94351
0.8182	Intermediate Similarity	NPC168303
0.7941	Intermediate Similarity	NPC486908
0.7879	Intermediate Similarity	NPC53051
0.7879	Intermediate Similarity	NPC24404
0.7879	Intermediate Similarity	NPC313030
0.75	Intermediate Similarity	NPC71002
0.75	Intermediate Similarity	NPC249828
0.7273	Intermediate Similarity	NPC470700
0.7273	Intermediate Similarity	NPC54844
0.7273	Intermediate Similarity	NPC39097
0.7273	Intermediate Similarity	NPC302681
0.7273	Intermediate Similarity	NPC241891
0.7273	Intermediate Similarity	NPC118286
0.7273	Intermediate Similarity	NPC134829
0.7273	Intermediate Similarity	NPC109691
0.7027	Intermediate Similarity	NPC302219
0.6857	Remote Similarity	NPC39664
0.6765	Remote Similarity	NPC3358
0.6765	Remote Similarity	NPC306884
0.6765	Remote Similarity	NPC603092
0.6667	Remote Similarity	NPC59506
0.6579	Remote Similarity	NPC242342
0.6579	Remote Similarity	NPC85479
0.6471	Remote Similarity	NPC488411
0.6471	Remote Similarity	NPC488410
0.6471	Remote Similarity	NPC488409
0.6429	Remote Similarity	NPC486909
0.6364	Remote Similarity	NPC123273
0.6364	Remote Similarity	NPC318325
0.6316	Remote Similarity	NPC166761
0.6279	Remote Similarity	NPC305603
0.6176	Remote Similarity	NPC37802
0.6154	Remote Similarity	NPC10588
0.6154	Remote Similarity	NPC284011
0.6	Remote Similarity	NPC114064
0.6	Remote Similarity	NPC72947
0.575	Remote Similarity	NPC94139
0.575	Remote Similarity	NPC147284
0.5745	Remote Similarity	NPC123559
0.5714	Remote Similarity	NPC244513
0.5641	Remote Similarity	NPC232523
0.5556	Remote Similarity	NPC61033
0.5526	Remote Similarity	NPC162113
0.5526	Remote Similarity	NPC62546
0.55	Remote Similarity	NPC488413
0.55	Remote Similarity	NPC473691
0.55	Remote Similarity	NPC483454
0.55	Remote Similarity	NPC477454
0.55	Remote Similarity	NPC162314
0.55	Remote Similarity	NPC488415
0.55	Remote Similarity	NPC488414
0.55	Remote Similarity	NPC488412
0.5405	Remote Similarity	NPC76938
0.5405	Remote Similarity	NPC32714
0.5366	Remote Similarity	NPC115808
0.5366	Remote Similarity	NPC135414
0.5294	Remote Similarity	NPC242240
0.5263	Remote Similarity	NPC487946
0.5263	Remote Similarity	NPC487945
0.5217	Remote Similarity	NPC127894
0.5217	Remote Similarity	NPC470759
0.5152	Remote Similarity	NPC210849
0.5143	Remote Similarity	NPC610566
0.5102	Remote Similarity	NPC140521

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC24407 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6105
0.1-0.2	2877
0.2-0.3	154
0.3-0.4	9
0.4-0.5	4
0.5-0.6	1
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
0.5135	Remote Similarity	NPD846	Phase 4

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