NPASS Compound

Natural Product: NPC320458

Natural Product ID	NPC320458
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Rel-Annosquatin-I
IUPAC Name	(2S)-4-[14-[(2R,5S)-5-[(1S,4R)-4-[(2S,5S)-5-[(1S,2S)-1,2-dihydroxyhexyl]oxolan-2-yl]-1,4-dihydroxybutyl]oxolan-2-yl]tetradecyl]-2-methyl-2H-furan-5-one
Synonyms	Rel-Annosquatin-I
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1933123
PubChem CID	57403970
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 111113 0 0 0 0 0 0 0 0999 V2000 -13.9613 2.2549 -0.1652 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8262 2.2429 0.8126 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6227 1.4715 0.2721 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9748 0.0478 -0.0176 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8692 -0.7793 -0.5758 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6419 -0.9331 0.2369 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5335 0.0402 0.0550 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0288 0.0731 -1.3516 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5421 -0.1005 -1.2172 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2813 0.0487 0.2362 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4712 -0.4374 0.8325 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9529 1.4067 0.6762 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9584 2.1847 -0.0204 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5460 1.9726 -0.2089 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8532 0.9035 -0.9115 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9668 -0.5010 -0.4575 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6431 -0.6128 0.9974 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2445 -2.1076 1.0303 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4223 -2.1353 -0.2422 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8871 -1.1897 -1.1058 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0438 -2.0328 0.0254 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5654 -3.1566 0.8588 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0569 -2.9868 1.1359 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8563 -2.9385 -0.1344 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3062 -2.7922 0.1918 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5222 -1.5181 0.9720 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0759 -1.4723 1.2364 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3821 -0.2475 2.0115 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7197 0.0501 2.4869 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8693 0.2404 1.5762 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3457 -0.8787 0.7453 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5489 -0.4884 -0.1424 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6667 -0.0643 0.7432 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9378 0.3138 0.0772 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9117 1.4985 -0.7928 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9769 2.3668 -1.1056 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4506 3.4022 -2.0443 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7907 3.0731 -2.2740 O 0 0 0 0 0 0 0 0 0 0 0 0 14.1105 1.9496 -1.5533 C 0 0 0 0 0 0 0 0 0 0 0 0 15.2312 1.3743 -1.5246 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6464 3.2596 -3.3337 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0417 0.9877 -2.3304 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7121 1.4110 2.0822 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0041 -1.0991 1.5799 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6517 -0.5226 -1.9196 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.3181 3.3170 -0.2520 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7130 1.8712 -1.1593 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.8197 1.7058 0.3023 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4741 3.2576 1.0808 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1035 1.7286 1.7598 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8250 1.4765 1.0736 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2283 2.0353 -0.5733 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7819 0.0816 -0.8113 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4946 -0.4415 0.8432 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2969 -1.8731 -0.6094 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1873 -1.9465 -0.0396 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7048 1.0624 0.3765 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2984 1.0179 -1.8833 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3769 -0.7698 -1.9841 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2089 -1.1071 -1.5922 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0358 0.6741 -1.8414 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5364 -0.7107 0.6471 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9763 1.9721 0.6543 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3597 2.4467 -1.1015 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0783 3.2857 0.4152 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1012 2.0264 0.8942 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0522 2.9806 -0.5823 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7036 1.1557 -0.8818 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8722 -0.9995 -0.7910 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4912 -0.4077 1.6364 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7235 -0.0556 1.2738 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1224 -2.7540 0.9815 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6257 -2.1960 1.9374 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6238 -3.1550 -0.6871 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5606 -2.0935 -0.9612 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2716 -1.0403 0.4343 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0301 -3.2944 1.8150 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4865 -4.1465 0.3331 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3522 -3.8063 1.8023 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2353 -2.0414 1.6937 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6461 -3.8058 -0.8012 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5811 -2.0394 -0.7558 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6016 -3.6782 0.8145 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9284 -2.8031 -0.7443 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1278 -1.6054 2.0036 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2086 -0.6289 0.4244 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2829 -2.4267 1.7417 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5369 -1.5045 0.2314 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0232 0.6735 1.4145 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6602 -0.1893 2.8962 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6505 0.9741 3.1687 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0151 -0.7394 3.2825 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7462 0.5541 2.2534 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6717 1.1616 0.9489 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6513 -1.3788 0.0815 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8270 -1.6267 1.4667 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7927 -1.4821 -0.6537 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1874 0.2089 -0.8815 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8322 -0.7523 1.5953 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3116 0.8958 1.2503 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6810 0.5118 0.9098 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4083 -0.5430 -0.4813 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9642 2.3276 -0.6945 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3326 4.4300 -1.6237 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3395 3.0887 -4.1929 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0194 4.1653 -3.5060 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9546 2.3939 -3.3109 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5660 1.7735 -2.6851 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1148 2.2005 2.2538 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8410 -1.6277 1.5966 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6407 -1.3637 -2.4179 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 10 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 19 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 1 0 35 36 2 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 37 41 1 0 15 42 1 0 12 43 1 0 6 44 1 0 5 45 1 0 11 7 1 0 20 16 1 0 39 35 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 6 56 1 0 7 57 1 0 8 58 1 0 8 59 1 0 9 60 1 0 9 61 1 0 10 62 1 0 12 63 1 0 13 64 1 0 13 65 1 0 14 66 1 0 14 67 1 0 15 68 1 0 16 69 1 0 17 70 1 0 17 71 1 0 18 72 1 0 18 73 1 0 19 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 26 85 1 0 26 86 1 0 27 87 1 0 27 88 1 0 28 89 1 0 28 90 1 0 29 91 1 0 29 92 1 0 30 93 1 0 30 94 1 0 31 95 1 0 31 96 1 0 32 97 1 0 32 98 1 0 33 99 1 0 33100 1 0 34101 1 0 34102 1 0 36103 1 0 37104 1 0 41105 1 0 41106 1 0 41107 1 0 42108 1 0 43109 1 0 44110 1 0 45111 1 0 M END

Standard InCHIKey	RWJFJCUKDFQLBE-PPRJGXARSA-N
Standard InCHI	InChI=1S/C37H66O8/c1-3-4-19-32(40)36(41)35-25-24-34(45-35)31(39)22-21-30(38)33-23-20-29(44-33)18-16-14-12-10-8-6-5-7-9-11-13-15-17-28-26-27(2)43-37(28)42/h26-27,29-36,38-41H,3-25H2,1-2H3/t27-,29+,30-,31+,32-,33-,34-,35-,36-/m0/s1
SMILES	CCCCC(C(C1CCC(O1)C(CCC(C2CCC(O2)CCCCCCCCCCCCCCC3=CC(OC3=O)C)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.48	Volume:	687.887 ? Van der Waals volume.
Dense:	0.928	LogP:	5.984 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.135 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.718 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	25.0	Rigid Bonds:	16.0
TPSA:	125.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.063	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.019	Fsp³:	0.919
MCE-18:	45.07 ? 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:	0.565	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.015 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.261	Promiscuous compounds:	0.004

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.168	MDCK Permeability:	-4.753
Pgp-inhibitor:	0.0	Pgp-substrate:	0.635
PAMPA:	0.408 ? 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):	0.971
20% Bioavailability (F20%):	0.96	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.987
Plasma Protein Binding (PPB):	97.396%	Volume Distribution (VD):	0.926
Fu:	2.679% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.21
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.553
BSEP inhibitor:	0.756

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.011	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.491	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.017
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.075
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.065
HLM stability:	0.114 ? 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):

5.407

Half-life (T1/2):

1.762

ADMET: Toxicity

hERG Blockers:	0.799	hERG Blockers (10um):	0.948
Human Hepatotoxicity (H-HT):	0.683	Drug-induced Liver Injury (DILI):	0.071
AMES Toxicity:	0.075	Rat Oral Acute Toxicity:	0.188
Maximum Recommended Daily Dose:	0.841	Skin Sensitization:	0.993
Carcinogencity:	0.047	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.29
Drug-induced Neurotoxicity:	0.088	Ototoxicity:	0.968
Hematotoxicity:	0.014	Drug-induced Nephrotoxicity:	0.625
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.073
A549 Cytotoxicity:	0.682	Hek293 Cytotoxicity:	0.729
BCF:	1.405 ? 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:	5.257 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.538 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.533 ? 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	6

Activity Type	# Activity
Cell line	6

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
NPT81	Cell line	A549	Homo sapiens	IC50	=	0.31	ug.mL-1	PMID[22011319]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	0.57	ug.mL-1	PMID[22011319]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	0.5	ug.mL-1	PMID[22011319]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	0.17	ug.mL-1	PMID[22011319]
NPT659	Cell line	SMMC-7721	Homo sapiens	IC50	=	0.11	ug.mL-1	PMID[22011319]
NPT1097	Cell line	MKN-45	Homo sapiens	IC50	=	0.14	ug.mL-1	PMID[22011319]

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 NPC320458 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	13606
0.1-0.2	33234
0.2-0.3	2728
0.3-0.4	71
0.4-0.5	69
0.5-0.6	77
0.6-0.7	58
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8269	Intermediate Similarity	NPC329615
0.8235	Intermediate Similarity	NPC241360
0.8235	Intermediate Similarity	NPC293136
0.8077	Intermediate Similarity	NPC65930
0.7636	Intermediate Similarity	NPC258068
0.7636	Intermediate Similarity	NPC476583
0.75	Intermediate Similarity	NPC480082
0.7273	Intermediate Similarity	NPC485250
0.7241	Intermediate Similarity	NPC322529
0.7119	Intermediate Similarity	NPC253801
0.7115	Intermediate Similarity	NPC329829
0.6863	Remote Similarity	NPC73310
0.6863	Remote Similarity	NPC473529
0.6863	Remote Similarity	NPC180363
0.6863	Remote Similarity	NPC94875
0.6863	Remote Similarity	NPC11332
0.6863	Remote Similarity	NPC145914
0.6863	Remote Similarity	NPC601174
0.6863	Remote Similarity	NPC601403
0.6863	Remote Similarity	NPC603568
0.6863	Remote Similarity	NPC604330
0.6863	Remote Similarity	NPC608300
0.6863	Remote Similarity	NPC611200
0.6863	Remote Similarity	NPC611571
0.6724	Remote Similarity	NPC231096
0.6724	Remote Similarity	NPC475581
0.6724	Remote Similarity	NPC62118
0.6724	Remote Similarity	NPC107717
0.6724	Remote Similarity	NPC488252
0.6667	Remote Similarity	NPC329838
0.6667	Remote Similarity	NPC20621
0.6667	Remote Similarity	NPC318963
0.6667	Remote Similarity	NPC605101
0.6552	Remote Similarity	NPC473478
0.6552	Remote Similarity	NPC473651
0.6552	Remote Similarity	NPC66346
0.6545	Remote Similarity	NPC156804
0.6481	Remote Similarity	NPC475159
0.6481	Remote Similarity	NPC131002
0.6481	Remote Similarity	NPC473780
0.6481	Remote Similarity	NPC604521
0.6441	Remote Similarity	NPC283085
0.6441	Remote Similarity	NPC132496
0.6441	Remote Similarity	NPC473995
0.6441	Remote Similarity	NPC606740
0.6441	Remote Similarity	NPC608614
0.6393	Remote Similarity	NPC473520
0.6333	Remote Similarity	NPC477014
0.6333	Remote Similarity	NPC477013
0.6316	Remote Similarity	NPC219652
0.6316	Remote Similarity	NPC473840
0.6182	Remote Similarity	NPC25764
0.6182	Remote Similarity	NPC235809
0.6182	Remote Similarity	NPC39279
0.6182	Remote Similarity	NPC39167
0.6182	Remote Similarity	NPC292809
0.6182	Remote Similarity	NPC202055
0.6182	Remote Similarity	NPC606804
0.6182	Remote Similarity	NPC607425
0.6182	Remote Similarity	NPC608574
0.614	Remote Similarity	NPC163093
0.614	Remote Similarity	NPC144415
0.614	Remote Similarity	NPC607439
0.614	Remote Similarity	NPC608157
0.6129	Remote Similarity	NPC480081
0.6078	Remote Similarity	NPC609415
0.6034	Remote Similarity	NPC25703
0.6032	Remote Similarity	NPC477015
0.6	Remote Similarity	NPC279267
0.5932	Remote Similarity	NPC132940
0.5893	Remote Similarity	NPC100921
0.5893	Remote Similarity	NPC477018
0.5873	Remote Similarity	NPC91067
0.5862	Remote Similarity	NPC473156
0.5862	Remote Similarity	NPC282815
0.5862	Remote Similarity	NPC600524
0.5862	Remote Similarity	NPC600956
0.5862	Remote Similarity	NPC608355
0.5833	Remote Similarity	NPC20533
0.5806	Remote Similarity	NPC233551
0.5806	Remote Similarity	NPC40376
0.5806	Remote Similarity	NPC21208
0.5763	Remote Similarity	NPC473671
0.5763	Remote Similarity	NPC475268
0.5763	Remote Similarity	NPC470400
0.5763	Remote Similarity	NPC77871
0.5763	Remote Similarity	NPC9678
0.5763	Remote Similarity	NPC319036
0.5763	Remote Similarity	NPC605867
0.5738	Remote Similarity	NPC477012
0.5645	Remote Similarity	NPC169511
0.5645	Remote Similarity	NPC287164
0.5645	Remote Similarity	NPC234077
0.5593	Remote Similarity	NPC134865
0.5593	Remote Similarity	NPC103523
0.5593	Remote Similarity	NPC488627
0.5593	Remote Similarity	NPC488631
0.5593	Remote Similarity	NPC477011
0.5593	Remote Similarity	NPC610454
0.5574	Remote Similarity	NPC605396
0.5538	Remote Similarity	NPC473905
0.5439	Remote Similarity	NPC606043
0.5424	Remote Similarity	NPC232555
0.5424	Remote Similarity	NPC171174
0.5424	Remote Similarity	NPC114694
0.5424	Remote Similarity	NPC485248
0.5424	Remote Similarity	NPC142117
0.5424	Remote Similarity	NPC480249
0.5424	Remote Similarity	NPC485249
0.5424	Remote Similarity	NPC240695
0.5397	Remote Similarity	NPC120398
0.5397	Remote Similarity	NPC471567
0.5385	Remote Similarity	NPC280612
0.5345	Remote Similarity	NPC107986
0.5345	Remote Similarity	NPC223871
0.5345	Remote Similarity	NPC231009
0.5345	Remote Similarity	NPC103284
0.5345	Remote Similarity	NPC110710
0.5345	Remote Similarity	NPC1083
0.5345	Remote Similarity	NPC82795
0.5345	Remote Similarity	NPC286338
0.5345	Remote Similarity	NPC603931
0.5345	Remote Similarity	NPC604237
0.5333	Remote Similarity	NPC488632
0.5333	Remote Similarity	NPC473649
0.5333	Remote Similarity	NPC154097
0.5333	Remote Similarity	NPC159750
0.5333	Remote Similarity	NPC73248
0.5333	Remote Similarity	NPC47937
0.5333	Remote Similarity	NPC470401
0.5323	Remote Similarity	NPC309211
0.5323	Remote Similarity	NPC477010
0.5294	Remote Similarity	NPC482766
0.5294	Remote Similarity	NPC477017
0.5294	Remote Similarity	NPC477016
0.5254	Remote Similarity	NPC488253
0.5254	Remote Similarity	NPC473669
0.5254	Remote Similarity	NPC488251
0.5246	Remote Similarity	NPC280621
0.5246	Remote Similarity	NPC48338
0.5246	Remote Similarity	NPC488628
0.5246	Remote Similarity	NPC604764
0.5167	Remote Similarity	NPC182383
0.5152	Remote Similarity	NPC488630
0.5152	Remote Similarity	NPC488625
0.5152	Remote Similarity	NPC488626

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC320458 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5628
0.1-0.2	3480
0.2-0.3	42
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