NPASS Compound

Natural Product: NPC329838

Natural Product ID	NPC329838
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Squadiolin A
IUPAC Name	(2S)-4-[(13R,14R,17R)-17-[(2R,5R)-5-[(1S)-1,5-dihydroxyundecyl]oxolan-2-yl]-13,14,17-trihydroxyheptadecyl]-2-methyl-2H-furan-5-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL448701
PubChem CID	44577074
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

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 113114 0 0 0 0 0 0 0 0999 V2000 -13.6883 -2.0200 0.6826 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5482 -0.8219 -0.1988 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4617 -0.9668 -1.2574 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1535 -1.1805 -0.5843 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9644 -1.3165 -1.4683 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6845 -0.1191 -2.3471 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4448 1.1290 -1.6168 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3736 1.2901 -0.6461 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9534 1.1839 -0.9521 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5033 -0.1265 -1.4703 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0005 -0.1492 -1.7274 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1654 0.1011 -0.5216 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2530 -1.0544 0.4725 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1724 -1.9707 -0.0182 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2323 -1.0451 -0.7540 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8389 0.1686 -0.8558 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8508 -1.0411 -0.1557 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7601 -0.5922 1.2497 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2017 0.7770 1.5785 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4165 1.8689 0.8854 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0522 1.8219 1.2616 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7383 3.1139 0.8194 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2207 3.0633 1.2116 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8978 1.9204 0.5475 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4015 1.9391 0.9063 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5711 1.7990 2.3522 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9411 1.8776 2.8883 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9470 0.9066 2.4412 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4324 0.9008 1.0581 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5264 -0.1723 0.8861 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0635 -1.5483 1.1601 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0564 -2.6475 1.0157 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6385 -2.9263 -0.3083 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4065 -1.8584 -0.9498 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1961 -1.3103 -2.1179 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2046 -0.2680 -2.3847 C 0 0 1 0 0 0 0 0 0 0 0 0 13.0302 -0.2640 -1.2542 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5743 -1.2202 -0.3552 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0722 -1.5021 0.7842 O 0 0 0 0 0 0 0 0 0 0 0 0 12.9596 -0.6932 -3.6468 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1445 1.8292 2.6616 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9746 3.0760 1.3882 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3958 -2.3859 -0.1712 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6711 -1.3703 -2.2809 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6606 1.4897 -0.9566 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.7745 -2.1096 1.2991 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.5316 -1.9086 1.3703 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7721 -2.9578 0.0938 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2939 0.0554 0.4694 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.5384 -0.5881 -0.6449 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7447 -1.9212 -1.8019 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5164 -0.1893 -2.0132 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0015 -0.4392 0.2480 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2252 -2.1644 -0.0173 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0664 -2.2406 -2.0991 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0778 -1.4886 -0.8247 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0467 -0.4142 -3.1648 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7042 0.0485 -2.8789 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3701 1.9909 -2.3909 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5612 2.3158 -0.1440 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5882 0.6096 0.2683 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5453 2.0467 -1.5525 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3973 1.3359 0.0395 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9481 -0.3712 -2.4467 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7202 -0.9694 -0.7871 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8222 0.6058 -2.5378 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4245 1.0164 0.0510 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9777 -0.6663 1.4699 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2503 -1.5370 0.4822 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6437 -2.7269 -0.6935 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6953 -2.5276 0.8004 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1274 -1.4654 -1.7883 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1813 -0.4738 -0.7942 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2330 -1.2904 1.9796 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3389 -0.6437 1.5164 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2799 0.9890 1.4579 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0208 0.9670 2.6837 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5118 1.8963 -0.1942 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5242 0.9740 0.7775 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3134 3.9400 1.4162 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6724 3.2880 -0.2634 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6889 4.0077 0.9187 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2564 2.9362 2.3194 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5483 0.9370 0.9509 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8218 1.9269 -0.5487 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7650 1.0510 0.3194 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8377 2.8507 0.4713 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0083 2.6403 2.9165 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0204 0.8942 2.7681 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3528 2.9459 2.7809 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9287 1.7989 4.0370 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8620 1.0228 3.1065 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5382 -0.1128 2.7548 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0048 1.8667 0.8797 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7661 0.7284 0.2326 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9532 -0.0219 -0.1105 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3328 0.1572 1.6012 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2309 -1.7832 0.4129 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5256 -1.6392 2.1396 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9209 -2.4811 1.7569 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6217 -3.6184 1.3903 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7915 -3.1774 -1.0344 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2408 -3.9010 -0.2980 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4025 -1.5521 -2.8317 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7004 0.7072 -2.5547 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2853 -0.4489 -4.4992 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0601 -1.7986 -3.5781 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9414 -0.2134 -3.7392 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4993 0.9543 2.9390 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1287 2.9465 2.3699 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2473 -2.5569 0.5612 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4946 -1.9411 -2.4138 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4927 2.2028 -0.2927 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 15 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 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 36 40 1 0 21 41 1 0 20 42 1 0 17 43 1 0 11 44 1 0 7 45 1 0 16 12 1 0 38 34 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 0 2 50 1 0 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 5 55 1 0 5 56 1 0 6 57 1 0 6 58 1 0 7 59 1 0 8 60 1 0 8 61 1 0 9 62 1 0 9 63 1 0 10 64 1 0 10 65 1 0 11 66 1 6 12 67 1 1 13 68 1 0 13 69 1 0 14 70 1 0 14 71 1 0 15 72 1 6 17 73 1 6 18 74 1 0 18 75 1 0 19 76 1 0 19 77 1 0 20 78 1 6 21 79 1 6 22 80 1 0 22 81 1 0 23 82 1 0 23 83 1 0 24 84 1 0 24 85 1 0 25 86 1 0 25 87 1 0 26 88 1 0 26 89 1 0 27 90 1 0 27 91 1 0 28 92 1 0 28 93 1 0 29 94 1 0 29 95 1 0 30 96 1 0 30 97 1 0 31 98 1 0 31 99 1 0 32100 1 0 32101 1 0 33102 1 0 33103 1 0 35104 1 0 36105 1 6 40106 1 0 40107 1 0 40108 1 0 41109 1 0 42110 1 0 43111 1 0 44112 1 0 45113 1 0 M END

Standard InCHIKey	HCSSMEMSGLDFIN-GHTOWDLGSA-N
Standard InCHI	InChI=1S/C37H68O8/c1-3-4-5-15-19-30(38)20-17-22-33(41)35-25-26-36(45-35)34(42)24-23-32(40)31(39)21-16-13-11-9-7-6-8-10-12-14-18-29-27-28(2)44-37(29)43/h27-28,30-36,38-42H,3-26H2,1-2H3/t28-,30?,31+,32+,33-,34+,35+,36+/m0/s1
SMILES	CCCCCCC(CCC[C@@H]([C@H]1CC[C@@H](O1)[C@@H](CC[C@H]([C@@H](CCCCCCCCCCCCC1=C[C@@H](OC1=O)C)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	640.49	Volume:	696.444 ? Van der Waals volume.
Dense:	0.92	LogP:	5.207 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.681 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.984 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	28.0	Rigid Bonds:	11.0
TPSA:	136.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	5.0	Rings:	2.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.046	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.829	Fsp³:	0.919
MCE-18:	34.254 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.836	Fluc inhibitor:	0.027 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.108 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.526	Promiscuous compounds:	0.151

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.215	MDCK Permeability:	-4.829
Pgp-inhibitor:	0.0	Pgp-substrate:	0.966
PAMPA:	0.193 ? 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):	0.7
20% Bioavailability (F20%):	0.991	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.873
Plasma Protein Binding (PPB):	94.196%	Volume Distribution (VD):	0.286
Fu:	4.591% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.648
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.654
BSEP inhibitor:	0.15

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.007
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.661
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.005 ? 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):

5.434

Half-life (T1/2):

1.255

ADMET: Toxicity

hERG Blockers:	0.478	hERG Blockers (10um):	0.826
Human Hepatotoxicity (H-HT):	0.751	Drug-induced Liver Injury (DILI):	0.113
AMES Toxicity:	0.217	Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.868	Skin Sensitization:	1.0
Carcinogencity:	0.227	Eye Corrosion:	0.017
Eye Irritation:	0.603	Respiratory Toxicity:	0.951
Drug-induced Neurotoxicity:	0.042	Ototoxicity:	0.884
Hematotoxicity:	0.06	Drug-induced Nephrotoxicity:	0.976
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.071
A549 Cytotoxicity:	0.966	Hek293 Cytotoxicity:	0.218
BCF:	1.158 ? 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:	5.133 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.397 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.174 ? 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
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	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	5

Activity Type	# Activity
Cell line	4
Non-molecular	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
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	630.0	nM	PMID[16252924]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	2830.0	nM	PMID[137981]
NPT81	Cell line	A549	Homo sapiens	IC50	<	200.0	nM	DOI[10.6019/CHEMBL1201861]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	5.6	nM	PMID[24128115]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	3520.0	nM	PMID[18419154]

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 NPC329838 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	17027
0.1-0.2	29840
0.2-0.3	2682
0.3-0.4	82
0.4-0.5	27
0.5-0.6	29
0.6-0.7	71
0.7-0.8	0
0.8-0.85	26
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8723	High Similarity	NPC156804
0.8696	High Similarity	NPC329829
0.8696	High Similarity	NPC475159
0.8696	High Similarity	NPC131002
0.8696	High Similarity	NPC473780
0.8696	High Similarity	NPC604521
0.8163	Intermediate Similarity	NPC477011
0.8077	Intermediate Similarity	NPC258068
0.8077	Intermediate Similarity	NPC476583
0.8043	Intermediate Similarity	NPC73310
0.8043	Intermediate Similarity	NPC473529
0.8043	Intermediate Similarity	NPC180363
0.8043	Intermediate Similarity	NPC94875
0.8043	Intermediate Similarity	NPC11332
0.8043	Intermediate Similarity	NPC145914
0.8043	Intermediate Similarity	NPC601174
0.8043	Intermediate Similarity	NPC601403
0.8043	Intermediate Similarity	NPC603568
0.8043	Intermediate Similarity	NPC604330
0.8043	Intermediate Similarity	NPC608300
0.8043	Intermediate Similarity	NPC611200
0.8043	Intermediate Similarity	NPC611571
0.8039	Intermediate Similarity	NPC20533
0.8	Intermediate Similarity	NPC473671
0.8	Intermediate Similarity	NPC219652
0.8	Intermediate Similarity	NPC475268
0.8	Intermediate Similarity	NPC473840
0.8	Intermediate Similarity	NPC470400
0.8	Intermediate Similarity	NPC77871
0.8	Intermediate Similarity	NPC9678
0.8	Intermediate Similarity	NPC319036
0.8	Intermediate Similarity	NPC605867
0.7917	Intermediate Similarity	NPC100921
0.7917	Intermediate Similarity	NPC477018
0.7843	Intermediate Similarity	NPC132940
0.78	Intermediate Similarity	NPC473156
0.78	Intermediate Similarity	NPC134865
0.78	Intermediate Similarity	NPC163093
0.78	Intermediate Similarity	NPC103523
0.78	Intermediate Similarity	NPC282815
0.78	Intermediate Similarity	NPC488627
0.78	Intermediate Similarity	NPC488631
0.78	Intermediate Similarity	NPC600956
0.7692	Intermediate Similarity	NPC329615
0.75	Intermediate Similarity	NPC65930
0.7451	Intermediate Similarity	NPC488632
0.7451	Intermediate Similarity	NPC610454
0.74	Intermediate Similarity	NPC488253
0.74	Intermediate Similarity	NPC488251
0.7308	Intermediate Similarity	NPC25703
0.7308	Intermediate Similarity	NPC241360
0.7308	Intermediate Similarity	NPC293136
0.7308	Intermediate Similarity	NPC604764
0.7273	Intermediate Similarity	NPC477014
0.7273	Intermediate Similarity	NPC477013
0.7255	Intermediate Similarity	NPC232555
0.7255	Intermediate Similarity	NPC171174
0.7255	Intermediate Similarity	NPC114694
0.7255	Intermediate Similarity	NPC485248
0.7255	Intermediate Similarity	NPC142117
0.7255	Intermediate Similarity	NPC480249
0.7255	Intermediate Similarity	NPC485249
0.7255	Intermediate Similarity	NPC240695
0.7222	Intermediate Similarity	NPC477012
0.72	Intermediate Similarity	NPC107986
0.72	Intermediate Similarity	NPC25764
0.72	Intermediate Similarity	NPC235809
0.72	Intermediate Similarity	NPC223871
0.72	Intermediate Similarity	NPC231009
0.72	Intermediate Similarity	NPC103284
0.72	Intermediate Similarity	NPC110710
0.72	Intermediate Similarity	NPC39279
0.72	Intermediate Similarity	NPC1083
0.72	Intermediate Similarity	NPC39167
0.72	Intermediate Similarity	NPC82795
0.72	Intermediate Similarity	NPC292809
0.72	Intermediate Similarity	NPC286338
0.72	Intermediate Similarity	NPC202055
0.72	Intermediate Similarity	NPC603931
0.72	Intermediate Similarity	NPC604237
0.72	Intermediate Similarity	NPC606804
0.72	Intermediate Similarity	NPC607425
0.72	Intermediate Similarity	NPC608574
0.7174	Intermediate Similarity	NPC609415
0.7115	Intermediate Similarity	NPC473649
0.7115	Intermediate Similarity	NPC154097
0.7115	Intermediate Similarity	NPC144415
0.7115	Intermediate Similarity	NPC159750
0.7115	Intermediate Similarity	NPC73248
0.7115	Intermediate Similarity	NPC470401
0.7115	Intermediate Similarity	NPC600524
0.7115	Intermediate Similarity	NPC607439
0.7115	Intermediate Similarity	NPC608157
0.7115	Intermediate Similarity	NPC608355
0.7059	Intermediate Similarity	NPC473669
0.7037	Intermediate Similarity	NPC309211
0.7037	Intermediate Similarity	NPC485250
0.7037	Intermediate Similarity	NPC477010
0.7	Intermediate Similarity	NPC606043
0.6897	Remote Similarity	NPC473905
0.6852	Remote Similarity	NPC178215
0.6786	Remote Similarity	NPC231096
0.6786	Remote Similarity	NPC475581
0.6786	Remote Similarity	NPC120398
0.6786	Remote Similarity	NPC62118
0.6786	Remote Similarity	NPC107717
0.6786	Remote Similarity	NPC488252
0.6786	Remote Similarity	NPC471567
0.6724	Remote Similarity	NPC280612
0.6667	Remote Similarity	NPC280621
0.6667	Remote Similarity	NPC48338
0.6667	Remote Similarity	NPC320458
0.6667	Remote Similarity	NPC233551
0.6667	Remote Similarity	NPC40376
0.6667	Remote Similarity	NPC480082
0.6667	Remote Similarity	NPC21208
0.6667	Remote Similarity	NPC488628
0.661	Remote Similarity	NPC253801
0.6607	Remote Similarity	NPC473478
0.6607	Remote Similarity	NPC69082
0.6607	Remote Similarity	NPC473651
0.6607	Remote Similarity	NPC488249
0.6607	Remote Similarity	NPC66346
0.6604	Remote Similarity	NPC182383
0.6545	Remote Similarity	NPC42598
0.6491	Remote Similarity	NPC283085
0.6491	Remote Similarity	NPC132496
0.6491	Remote Similarity	NPC606740
0.6491	Remote Similarity	NPC608614
0.6481	Remote Similarity	NPC93794
0.6481	Remote Similarity	NPC473504
0.6481	Remote Similarity	NPC81778
0.6481	Remote Similarity	NPC40066
0.6481	Remote Similarity	NPC47937
0.6441	Remote Similarity	NPC322529
0.6429	Remote Similarity	NPC20621
0.6429	Remote Similarity	NPC318963
0.6429	Remote Similarity	NPC488250
0.6429	Remote Similarity	NPC605101
0.6429	Remote Similarity	NPC605396
0.6379	Remote Similarity	NPC89001
0.6296	Remote Similarity	NPC81045
0.6296	Remote Similarity	NPC39754
0.6296	Remote Similarity	NPC171135
0.6296	Remote Similarity	NPC61257
0.6296	Remote Similarity	NPC320569
0.6296	Remote Similarity	NPC133730
0.6296	Remote Similarity	NPC191929
0.6296	Remote Similarity	NPC100454
0.6296	Remote Similarity	NPC242364
0.6296	Remote Similarity	NPC172821
0.6296	Remote Similarity	NPC274446
0.6296	Remote Similarity	NPC485251
0.6296	Remote Similarity	NPC151403
0.6296	Remote Similarity	NPC261952
0.6296	Remote Similarity	NPC605171
0.625	Remote Similarity	NPC473687
0.625	Remote Similarity	NPC204686
0.625	Remote Similarity	NPC219498
0.625	Remote Similarity	NPC473904
0.625	Remote Similarity	NPC308412
0.625	Remote Similarity	NPC134885
0.625	Remote Similarity	NPC488247
0.625	Remote Similarity	NPC210218
0.625	Remote Similarity	NPC488248
0.6207	Remote Similarity	NPC473995
0.6167	Remote Similarity	NPC91067
0.6066	Remote Similarity	NPC477015
0.6032	Remote Similarity	NPC477017
0.6032	Remote Similarity	NPC477016
0.5932	Remote Similarity	NPC130359
0.5932	Remote Similarity	NPC14901
0.5902	Remote Similarity	NPC473520
0.5902	Remote Similarity	NPC480081
0.5862	Remote Similarity	NPC134807
0.5862	Remote Similarity	NPC602738
0.5833	Remote Similarity	NPC488623
0.5833	Remote Similarity	NPC488624
0.5833	Remote Similarity	NPC488629
0.58	Remote Similarity	NPC608138
0.5789	Remote Similarity	NPC480079
0.5763	Remote Similarity	NPC20339
0.5667	Remote Similarity	NPC169511
0.5667	Remote Similarity	NPC287164
0.5667	Remote Similarity	NPC234077
0.5645	Remote Similarity	NPC488630
0.5645	Remote Similarity	NPC488625
0.5645	Remote Similarity	NPC488626
0.5614	Remote Similarity	NPC488246
0.5614	Remote Similarity	NPC480080
0.5593	Remote Similarity	NPC600188
0.5556	Remote Similarity	NPC112685
0.5538	Remote Similarity	NPC279267
0.5484	Remote Similarity	NPC239517
0.5246	Remote Similarity	NPC139418
0.5231	Remote Similarity	NPC473663
0.5231	Remote Similarity	NPC473723
0.5231	Remote Similarity	NPC475173
0.5167	Remote Similarity	NPC478998

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC329838 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6563
0.1-0.2	2539
0.2-0.3	48
0.3-0.4	0
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