NPASS Compound

Natural Product: NPC168707

Natural Product ID	NPC168707
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2,7,8-Trimethyl-2-(4,8,12-Trimethyltridecyl)-3,4-Dihydrochromen-6-Ol
IUPAC Name	2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydrochromen-6-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL420898
PubChem CID	14986
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0001546] Vitamin E compounds [CHEMONTID:0000201] Tocopherols

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 78 79 0 0 0 0 0 0 0 0999 V2000 -6.9901 -1.3995 -1.5357 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3026 -2.2742 -0.5405 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4183 -2.6853 0.4543 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1898 -1.7352 0.2462 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9590 -1.2502 -0.3505 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8154 -0.1457 -1.2777 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1789 1.2310 -0.9283 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5973 1.5385 -0.5714 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3299 1.8415 0.1674 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8748 1.9278 -0.1327 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2199 2.5702 1.0760 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2471 2.7304 0.9354 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6505 3.5974 -0.2350 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9002 1.3676 0.6856 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6228 0.4352 1.8385 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2201 -0.9194 1.6806 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7030 -0.9774 1.5482 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4379 -0.4011 2.7261 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0513 -2.4708 1.3954 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5430 -2.6644 1.4800 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1887 -1.7385 0.5108 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4839 -1.9838 0.1202 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1031 -1.1440 -0.7739 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4487 -0.0404 -1.3005 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1713 0.8154 -2.2519 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1614 0.1712 -0.8884 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4225 1.3470 -1.4310 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5114 -0.6665 0.0177 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2045 -0.3709 0.3764 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3932 -1.4189 -1.1405 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5036 -0.5753 -0.9529 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3829 -1.0239 -2.3510 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8856 -1.9440 -1.9913 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0531 -3.2363 -1.0714 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3482 -2.8264 -0.1297 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5763 -1.8188 1.1257 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1199 -3.5713 1.0291 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8524 -2.6381 0.9132 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6020 -1.0717 1.0748 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3834 -2.1699 -0.7755 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2568 -1.0008 0.5435 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2025 -0.3860 -2.3169 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6776 -0.0892 -1.5245 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9556 1.8806 -1.8381 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2476 1.3686 -1.4599 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6347 2.6554 -0.4253 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9149 1.0742 0.3504 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7896 2.8052 0.4491 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4472 1.1741 1.0670 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4832 0.8818 -0.2351 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6354 2.4386 -1.0664 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6411 3.6079 1.2406 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5139 2.0181 1.9840 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7369 3.1474 1.8364 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7673 3.5506 -0.2852 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4148 4.6706 -0.0294 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2736 3.2389 -1.1951 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0119 1.5744 0.7077 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5867 0.9561 -0.2740 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8712 0.9320 2.7923 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4958 0.2872 1.8691 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8116 -1.3234 0.7024 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8246 -1.6417 2.4297 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5557 -1.1171 3.5563 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9496 0.5421 3.0312 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4617 -0.1356 2.3839 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5015 -3.0471 2.1591 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6865 -2.7932 0.4069 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9283 -2.5562 2.4953 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7604 -3.6998 1.1290 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0111 -2.8559 0.5318 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0602 0.2913 -2.6498 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5344 1.1818 -3.0933 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4822 1.7560 -1.7090 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6170 1.5295 -2.4926 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7041 2.2656 -0.8675 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3185 1.1771 -1.2792 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1453 -0.7708 -1.0974 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 24 26 1 0 26 27 1 0 26 28 2 0 28 29 1 0 23 30 1 0 29 17 1 0 28 21 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 0 3 35 1 0 3 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 5 40 1 0 5 41 1 0 6 42 1 0 6 43 1 0 7 44 1 0 8 45 1 0 8 46 1 0 8 47 1 0 9 48 1 0 9 49 1 0 10 50 1 0 10 51 1 0 11 52 1 0 11 53 1 0 12 54 1 0 13 55 1 0 13 56 1 0 13 57 1 0 14 58 1 0 14 59 1 0 15 60 1 0 15 61 1 0 16 62 1 0 16 63 1 0 18 64 1 0 18 65 1 0 18 66 1 0 19 67 1 0 19 68 1 0 20 69 1 0 20 70 1 0 22 71 1 0 25 72 1 0 25 73 1 0 25 74 1 0 27 75 1 0 27 76 1 0 27 77 1 0 30 78 1 0 M END

Standard InCHIKey	QUEDXNHFTDJVIY-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3
SMILES	CC(C)CCCC(C)CCCC(C)CCCC1(C)CCc2cc(c(C)c(C)c2O1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	416.37	Volume:	485.402 ? Van der Waals volume.
Dense:	0.858	LogP:	9.614 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.541 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.641 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	11.0
TPSA:	29.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	2.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.37	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.786	Fsp³:	0.786
MCE-18:	53.04 ? 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:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.92	Fluc inhibitor:	0.325 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.092 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.507	Promiscuous compounds:	0.024

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.973	MDCK Permeability:	-4.762
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.004 ? 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%):	0.001	30% Bioavailability (F30%):	0.074
50% Bioavailability (F50%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	1.0	MRP1:	0.998
Plasma Protein Binding (PPB):	96.763%	Volume Distribution (VD):	0.482
Fu:	3.905% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.833
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.087
BSEP inhibitor:	0.003

ADMET: Metabolism

CYP1A2-inhibitor:	0.788	CYP1A2-substrate:	0.988
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.987	CYP2C9-substrate:	0.423
CYP2D6-inhibitor:	0.995	CYP2D6-substrate:	0.73
CYP3A4-inhibitor:	0.301	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.159	CYP2C8-inhibitor:	1.0
HLM stability:	0.996 ? 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):

4.223

Half-life (T1/2):

0.531

ADMET: Toxicity

hERG Blockers:	0.354	hERG Blockers (10um):	0.862
Human Hepatotoxicity (H-HT):	0.652	Drug-induced Liver Injury (DILI):	0.008
AMES Toxicity:	0.196	Rat Oral Acute Toxicity:	0.128
Maximum Recommended Daily Dose:	0.324	Skin Sensitization:	0.991
Carcinogencity:	0.365	Eye Corrosion:	0.635
Eye Irritation:	0.967	Respiratory Toxicity:	0.898
Drug-induced Neurotoxicity:	0.035	Ototoxicity:	0.673
Hematotoxicity:	0.221	Drug-induced Nephrotoxicity:	0.062
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.134
A549 Cytotoxicity:	0.245	Hek293 Cytotoxicity:	0.09
BCF:	2.157 ? 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:	5.594 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.76 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.121 ? 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
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s00217-007-0799-1]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1016/j.foodchem.2011.01.077]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[10670815]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	seed	n.a.	PMID[11540412]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15620261]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	Malatya Fruit Research Institute	between the first and third weeks of 2005-Jul.	PMID[18038980]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[18496782]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[2082684]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21922656]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24176362]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25466114]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[25466198]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28737396]
NPO26277	Euphorbia hirta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141299]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[3254039]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[3256207]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35357239]
NPO48809	Impatiens textori	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36422527]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36431782]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36560643]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39138188]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39527985]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	twig	n.a.	PMID[9179367]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26277	Euphorbia hirta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8108.1	Citrullus lanatus subsp. vulgaris	Subspecies	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25099	Prunus mandshurica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20032	Prunus sibirica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4545	Canavalia gladiata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Embryo	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Twig	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26277	Euphorbia hirta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4545	Canavalia gladiata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO8108.1	Citrullus lanatus subsp. vulgaris	Subspecies	Cucurbitaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO8108.1	Citrullus lanatus subsp. vulgaris	Subspecies	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4545	Canavalia gladiata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26277	Euphorbia hirta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4545	Canavalia gladiata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26277	Euphorbia hirta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4545	Canavalia gladiata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25099	Prunus mandshurica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20032	Prunus sibirica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26277	Euphorbia hirta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4545	Canavalia gladiata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20032	Prunus sibirica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7808	Viscum album	Species	Viscaceae	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
NPO48809	Impatiens textori	n.a.	Flowers	0.08	n.a.	n.a.	%	PMID[36422527]

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
Inhibition	2
IC50	10

Activity Type	# Activity
Cell line	2
Others	10

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
NPT65	Cell line	HepG2	Homo sapiens	Inhibition	=	3.0	%	PMID[1433170]
NPT65	Cell line	HepG2	Homo sapiens	Inhibition	=	0.0	%	PMID[1433170]
NPT2	Others	Unspecified	n.a.	IC50	n.a.	20000.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	IC50	n.a.	10000.0	nM	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 NPC168707 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	22114
0.1-0.2	26081
0.2-0.3	1595
0.3-0.4	53
0.4-0.5	6
0.5-0.6	3
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC48623
0.7222	Intermediate Similarity	NPC187993
0.7222	Intermediate Similarity	NPC238176
0.6852	Remote Similarity	NPC126759
0.6852	Remote Similarity	NPC242580
0.6852	Remote Similarity	NPC236070
0.5902	Remote Similarity	NPC45663
0.5517	Remote Similarity	NPC238075
0.507	Remote Similarity	NPC609806

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC168707 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4337
0.1-0.2	4757
0.2-0.3	49
0.3-0.4	3
0.4-0.5	2
0.5-0.6	1
0.6-0.7	1
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
0.6852	Remote Similarity	NPD7340	Approved
0.5517	Remote Similarity	NPD7644	Approved

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