NPASS Compound

Natural Product: NPC25703

Natural Product ID	NPC25703
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Bullatetrocin
IUPAC Name	(2S)-4-[(13R)-13-hydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1S,8R,9S)-1,8,9-trihydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
Synonyms	Bullatetrocin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL451834
PubChem CID	10746683
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 -13.5123 1.2571 0.9518 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4508 1.2111 -0.1143 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7878 -0.1739 -0.1733 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.7637 -0.1064 -1.2520 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.9710 -1.3438 -1.4858 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1485 -1.8533 -0.3828 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1213 -1.0120 0.2060 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9789 -0.4598 -0.5609 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2449 0.5270 -1.6132 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1671 1.0205 -2.4811 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9506 1.6588 -1.9987 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0466 0.7972 -1.1888 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4255 -0.2231 -2.1631 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1234 -0.4952 -1.4472 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8103 0.8220 -0.8113 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1083 0.5624 0.5148 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9527 -0.1148 1.5296 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9794 -1.1064 2.1610 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0253 -1.3322 1.0096 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3961 -1.6020 1.5494 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3009 -1.5425 0.3680 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7419 -1.7727 0.6073 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4346 -0.7955 1.5178 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3835 0.6185 0.9742 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0537 0.7800 -0.3243 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4926 0.5726 -0.4877 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4822 1.4540 0.1250 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6532 1.6575 1.5587 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0022 0.5514 2.4411 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2068 -0.2811 2.2781 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5374 0.3197 2.4211 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0415 1.3314 1.5058 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2573 0.8553 0.1225 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1289 -0.3306 -0.3737 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4465 -0.3327 -1.8117 C 0 0 2 0 0 0 0 0 0 0 0 0 12.6461 -1.2554 -1.9948 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8102 0.9771 -2.1178 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7000 1.7367 -0.9860 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9202 2.9768 -0.8352 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6440 -0.5492 2.4212 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0668 -0.1061 0.3630 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9691 1.4905 -0.6741 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2529 2.1998 -3.1184 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.4627 0.1518 -2.4567 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2397 -0.4239 1.0571 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.9838 0.2790 1.1384 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.3308 1.9277 0.5760 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1260 1.7507 1.8728 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7027 2.0079 0.0633 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9422 1.3811 -1.1109 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6269 -0.8646 -0.4276 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1012 0.7633 -1.0712 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7649 -2.2187 -1.6481 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5066 -1.3258 -2.4800 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8060 -2.2642 0.4628 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6447 -2.8395 -0.7149 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5851 -0.1461 0.8115 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6252 -1.5879 1.0790 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4269 0.1500 0.2785 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3015 -1.2493 -0.8901 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7014 1.4871 -1.1208 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1020 0.2671 -2.3110 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9139 0.1476 -3.2010 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6963 1.7150 -3.2463 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1528 2.5918 -1.3858 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4613 0.2059 -0.3900 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2164 0.2297 -3.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0577 -1.1101 -2.2839 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3301 -0.8222 -2.1600 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3483 -1.3087 -0.7100 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0705 1.3272 -1.4906 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8579 1.5858 0.9186 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3410 0.5950 2.2951 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8255 -0.6715 1.1342 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4609 -0.5969 3.0180 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5030 -2.0164 2.4777 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3859 -2.1531 0.3828 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3715 -2.5838 2.0545 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0928 -0.5894 -0.1697 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9498 -2.3439 -0.3439 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8464 -2.7827 1.1005 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2623 -1.7931 -0.3661 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9420 -0.7898 2.5054 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4535 -1.1893 1.6571 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2696 0.7942 0.7628 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6234 1.3388 1.7384 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8472 1.8634 -0.6496 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5188 0.2127 -1.1447 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6866 0.6177 -1.6205 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6943 -0.5265 -0.2924 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2477 2.5112 -0.3024 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5201 1.3091 -0.3395 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3703 2.5201 1.7030 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7140 2.1354 2.0313 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0994 -0.0794 2.7477 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1777 1.0701 3.4845 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1310 -1.0402 3.1723 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1080 -0.9663 1.3801 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3389 -0.5143 2.4671 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6474 0.6986 3.5254 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1023 1.6395 1.8985 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4543 2.2636 1.5209 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8555 -1.2781 0.1266 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5872 -0.6952 -2.4293 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9957 -1.2012 -3.0549 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4327 -0.9550 -1.2749 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3121 -2.2904 -1.8106 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5624 -0.8046 3.3734 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6673 1.9011 -3.9589 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8641 -0.7071 -2.8067 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6378 0.1616 1.7492 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 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 2 0 34 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 38 39 2 0 20 40 1 0 19 41 1 0 15 42 1 0 11 43 1 0 4 44 1 0 3 45 1 0 42 12 1 0 41 16 1 0 38 33 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 6 4 52 1 1 5 53 1 0 5 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 8 59 1 0 8 60 1 0 9 61 1 0 9 62 1 0 10 63 1 0 10 64 1 0 11 65 1 1 12 66 1 1 13 67 1 0 13 68 1 0 14 69 1 0 14 70 1 0 15 71 1 6 16 72 1 1 17 73 1 0 17 74 1 0 18 75 1 0 18 76 1 0 19 77 1 6 20 78 1 1 21 79 1 0 21 80 1 0 22 81 1 0 22 82 1 0 23 83 1 0 23 84 1 0 24 85 1 0 24 86 1 0 25 87 1 0 25 88 1 0 26 89 1 0 26 90 1 0 27 91 1 0 27 92 1 0 28 93 1 0 28 94 1 0 29 95 1 0 29 96 1 0 30 97 1 0 30 98 1 0 31 99 1 0 31100 1 0 32101 1 0 32102 1 0 34103 1 0 35104 1 6 36105 1 0 36106 1 0 36107 1 0 40108 1 0 43109 1 0 44110 1 0 45111 1 0 M END

Standard InCHIKey	FXUFAUVCSYAYLC-MKQHPUIBSA-N
Standard InCHI	InChI=1S/C37H66O8/c1-3-29(38)30(39)19-15-12-13-17-21-32(41)34-23-25-36(45-34)35-24-22-33(44-35)31(40)20-16-11-9-7-5-4-6-8-10-14-18-28-26-27(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	CC[C@@H]([C@@H](CCCCCC[C@@H]([C@H]1CC[C@H]([C@H]2CC[C@H]([C@@H](CCCCCCCCCCCCC3=C[C@H](C)OC3=O)O)O2)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.48	Volume:	687.887 ? Van der Waals volume.
Dense:	0.928	LogP:	5.095 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.605 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.875 ? 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:	4.947	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:	0.91	Fluc inhibitor:	0.036 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.1 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.531	Promiscuous compounds:	0.336

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.166	MDCK Permeability:	-4.789
Pgp-inhibitor:	0.006	Pgp-substrate:	0.922
PAMPA:	0.021 ? 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):	0.625
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.991
Plasma Protein Binding (PPB):	97.38%	Volume Distribution (VD):	0.74
Fu:	3.088% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.853
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.72
BSEP inhibitor:	0.814

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.01	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.989	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.963
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.991
HLM stability:	0.02 ? 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):

4.973

Half-life (T1/2):

1.313

ADMET: Toxicity

hERG Blockers:	0.459	hERG Blockers (10um):	0.687
Human Hepatotoxicity (H-HT):	0.799	Drug-induced Liver Injury (DILI):	0.235
AMES Toxicity:	0.732	Rat Oral Acute Toxicity:	0.262
Maximum Recommended Daily Dose:	0.826	Skin Sensitization:	1.0
Carcinogencity:	0.503	Eye Corrosion:	0.005
Eye Irritation:	0.357	Respiratory Toxicity:	0.894
Drug-induced Neurotoxicity:	0.169	Ototoxicity:	0.536
Hematotoxicity:	0.081	Drug-induced Nephrotoxicity:	0.734
Genotoxicity:	0.002	RPMI-8226 Immunitoxicity:	0.091
A549 Cytotoxicity:	0.975	Hek293 Cytotoxicity:	0.386
BCF:	1.368 ? 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:	5.137 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.414 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.898 ? 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
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11087592]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15730242]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	bark	n.a.	PMID[1593281]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30028612]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8676130]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8946743]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7697	Asimina triloba	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
ED50	12

Activity Type	# Activity
Cell line	12

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
NPT306	Cell line	PC-3	Homo sapiens	ED50	>	1.0	ug ml-1	DOI[10.6019/CHEMBL1201861]
NPT376	Cell line	A498	Homo sapiens	ED50	>	1.0	ug ml-1	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	3.32	10'-5 ug/ml	PMID[23957453]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	4.97	10'-1 ug/ml	PMID[22545792]
NPT81	Cell line	A549	Homo sapiens	ED50	=	3.52	10'-1 ug/ml	PMID[22931300]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	>	1.0	ug ml-1	PMID[22703109]
NPT81	Cell line	A549	Homo sapiens	ED50	=	3.5	10'-1 ug/ml	PMID[24411199]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	5.0	10'-1 ug/ml	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	3.3	10'-1 ug/ml	PMID[25443644]

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
-	Artemia	LC50	=	0.31	ug.mL-1	PMID[15387645]
-	Artemia salina	LC50	=	3.1	10'-1ppm	PMID[22703109]

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 NPC25703 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	16800
0.1-0.2	30210
0.2-0.3	2568
0.3-0.4	58
0.4-0.5	32
0.5-0.6	77
0.6-0.7	50
0.7-0.8	0
0.8-0.85	5
0.85-0.9	11
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.913	High Similarity	NPC219652
0.913	High Similarity	NPC473840
0.8667	High Similarity	NPC25764
0.8667	High Similarity	NPC235809
0.8667	High Similarity	NPC39279
0.8667	High Similarity	NPC39167
0.8667	High Similarity	NPC292809
0.8667	High Similarity	NPC202055
0.8667	High Similarity	NPC606804
0.8667	High Similarity	NPC607425
0.8667	High Similarity	NPC608574
0.8511	High Similarity	NPC600524
0.8511	High Similarity	NPC608355
0.8367	Intermediate Similarity	NPC485250
0.8261	Intermediate Similarity	NPC329829
0.8125	Intermediate Similarity	NPC473156
0.8125	Intermediate Similarity	NPC282815
0.8125	Intermediate Similarity	NPC600956
0.7959	Intermediate Similarity	NPC473671
0.7959	Intermediate Similarity	NPC475268
0.7959	Intermediate Similarity	NPC470400
0.7959	Intermediate Similarity	NPC77871
0.7959	Intermediate Similarity	NPC9678
0.7959	Intermediate Similarity	NPC319036
0.7959	Intermediate Similarity	NPC605867
0.78	Intermediate Similarity	NPC132940
0.7778	Intermediate Similarity	NPC473905
0.7755	Intermediate Similarity	NPC610454
0.7647	Intermediate Similarity	NPC20533
0.7647	Intermediate Similarity	NPC605396
0.7609	Intermediate Similarity	NPC73310
0.7609	Intermediate Similarity	NPC473529
0.7609	Intermediate Similarity	NPC180363
0.7609	Intermediate Similarity	NPC94875
0.7609	Intermediate Similarity	NPC11332
0.7609	Intermediate Similarity	NPC145914
0.7609	Intermediate Similarity	NPC601174
0.7609	Intermediate Similarity	NPC601403
0.7609	Intermediate Similarity	NPC603568
0.7609	Intermediate Similarity	NPC604330
0.7609	Intermediate Similarity	NPC608300
0.7609	Intermediate Similarity	NPC611200
0.7609	Intermediate Similarity	NPC611571
0.7451	Intermediate Similarity	NPC65930
0.74	Intermediate Similarity	NPC473649
0.74	Intermediate Similarity	NPC154097
0.74	Intermediate Similarity	NPC159750
0.74	Intermediate Similarity	NPC73248
0.74	Intermediate Similarity	NPC470401
0.7358	Intermediate Similarity	NPC120398
0.7358	Intermediate Similarity	NPC473995
0.7358	Intermediate Similarity	NPC471567
0.7308	Intermediate Similarity	NPC329838
0.7255	Intermediate Similarity	NPC604764
0.7143	Intermediate Similarity	NPC475159
0.7143	Intermediate Similarity	NPC131002
0.7143	Intermediate Similarity	NPC473780
0.7143	Intermediate Similarity	NPC604521
0.7111	Intermediate Similarity	NPC609415
0.6981	Remote Similarity	NPC329615
0.6964	Remote Similarity	NPC473520
0.6863	Remote Similarity	NPC81045
0.6863	Remote Similarity	NPC39754
0.6863	Remote Similarity	NPC171135
0.6863	Remote Similarity	NPC61257
0.6863	Remote Similarity	NPC320569
0.6863	Remote Similarity	NPC133730
0.6863	Remote Similarity	NPC191929
0.6863	Remote Similarity	NPC100454
0.6863	Remote Similarity	NPC242364
0.6863	Remote Similarity	NPC172821
0.6863	Remote Similarity	NPC156804
0.6863	Remote Similarity	NPC274446
0.6863	Remote Similarity	NPC485251
0.6863	Remote Similarity	NPC151403
0.6863	Remote Similarity	NPC261952
0.6863	Remote Similarity	NPC605171
0.6731	Remote Similarity	NPC93794
0.6731	Remote Similarity	NPC473504
0.6731	Remote Similarity	NPC163093
0.6731	Remote Similarity	NPC144415
0.6731	Remote Similarity	NPC81778
0.6731	Remote Similarity	NPC40066
0.6731	Remote Similarity	NPC607439
0.6731	Remote Similarity	NPC608157
0.6667	Remote Similarity	NPC91067
0.6607	Remote Similarity	NPC89001
0.6607	Remote Similarity	NPC480082
0.6604	Remote Similarity	NPC241360
0.6604	Remote Similarity	NPC293136
0.6552	Remote Similarity	NPC253801
0.6545	Remote Similarity	NPC477012
0.6481	Remote Similarity	NPC42598
0.6471	Remote Similarity	NPC100921
0.6471	Remote Similarity	NPC477018
0.6415	Remote Similarity	NPC134865
0.6415	Remote Similarity	NPC103523
0.6415	Remote Similarity	NPC488627
0.6415	Remote Similarity	NPC488631
0.6415	Remote Similarity	NPC477011
0.6364	Remote Similarity	NPC602738
0.614	Remote Similarity	NPC169511
0.614	Remote Similarity	NPC258068
0.614	Remote Similarity	NPC287164
0.614	Remote Similarity	NPC234077
0.614	Remote Similarity	NPC476583
0.6034	Remote Similarity	NPC320458
0.6034	Remote Similarity	NPC477014
0.6034	Remote Similarity	NPC477013
0.5965	Remote Similarity	NPC473478
0.5965	Remote Similarity	NPC473651
0.5965	Remote Similarity	NPC66346
0.5962	Remote Similarity	NPC606043
0.5932	Remote Similarity	NPC239517
0.5862	Remote Similarity	NPC283085
0.5862	Remote Similarity	NPC132496
0.5849	Remote Similarity	NPC107986
0.5849	Remote Similarity	NPC223871
0.5849	Remote Similarity	NPC231009
0.5849	Remote Similarity	NPC103284
0.5849	Remote Similarity	NPC110710
0.5849	Remote Similarity	NPC1083
0.5849	Remote Similarity	NPC82795
0.5849	Remote Similarity	NPC286338
0.5849	Remote Similarity	NPC603931
0.5849	Remote Similarity	NPC604237
0.5833	Remote Similarity	NPC322529
0.5789	Remote Similarity	NPC309211
0.5789	Remote Similarity	NPC477010
0.5741	Remote Similarity	NPC488253
0.5741	Remote Similarity	NPC473669
0.5741	Remote Similarity	NPC488251
0.5738	Remote Similarity	NPC477015
0.5714	Remote Similarity	NPC480079
0.5645	Remote Similarity	NPC473663
0.5645	Remote Similarity	NPC473723
0.5645	Remote Similarity	NPC475173
0.5636	Remote Similarity	NPC232555
0.5636	Remote Similarity	NPC171174
0.5636	Remote Similarity	NPC114694
0.5636	Remote Similarity	NPC485248
0.5636	Remote Similarity	NPC142117
0.5636	Remote Similarity	NPC480249
0.5636	Remote Similarity	NPC485249
0.5636	Remote Similarity	NPC240695
0.5593	Remote Similarity	NPC231096
0.5593	Remote Similarity	NPC475581
0.5593	Remote Similarity	NPC62118
0.5593	Remote Similarity	NPC107717
0.5593	Remote Similarity	NPC488252
0.5593	Remote Similarity	NPC606740
0.5593	Remote Similarity	NPC608614
0.5574	Remote Similarity	NPC280612
0.5536	Remote Similarity	NPC488632
0.5517	Remote Similarity	NPC600188
0.55	Remote Similarity	NPC233551
0.55	Remote Similarity	NPC40376
0.55	Remote Similarity	NPC21208
0.5439	Remote Similarity	NPC280621
0.5439	Remote Similarity	NPC48338
0.5439	Remote Similarity	NPC488628
0.5357	Remote Similarity	NPC182383
0.5345	Remote Similarity	NPC178215
0.5345	Remote Similarity	NPC473687
0.5345	Remote Similarity	NPC204686
0.5345	Remote Similarity	NPC219498
0.5345	Remote Similarity	NPC308412
0.5345	Remote Similarity	NPC134885
0.5345	Remote Similarity	NPC488247
0.5345	Remote Similarity	NPC210218
0.5345	Remote Similarity	NPC488248
0.5323	Remote Similarity	NPC480081
0.5254	Remote Similarity	NPC20621
0.5254	Remote Similarity	NPC318963
0.5254	Remote Similarity	NPC134807
0.5254	Remote Similarity	NPC488250
0.5254	Remote Similarity	NPC605101
0.5246	Remote Similarity	NPC488623
0.5246	Remote Similarity	NPC488624
0.5246	Remote Similarity	NPC488629
0.5227	Remote Similarity	NPC84038
0.5185	Remote Similarity	NPC112685
0.5167	Remote Similarity	NPC69082
0.5167	Remote Similarity	NPC488249
0.5082	Remote Similarity	NPC130359
0.5082	Remote Similarity	NPC14901

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC25703 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6474
0.1-0.2	2635
0.2-0.3	41
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