NPASS Compound

Natural Product: NPC477318

Natural Product ID	NPC477318
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2S,3R,4S,5R,6S)-6-[(2S,3S,4R,5R,6S)-6-[[(1R,3S,5S,6R,7R,8R,20S,22R,24R,25S,26S)-26-acetyloxy-7,25-dihydroxy-5,24-dimethyl-10-oxo-20-pentyl-2,4,9,21,23-pentaoxatricyclo[20.4.0.03,8]hexacosan-6-yl]oxy]-2-methyl-5-[(2S)-2-methylbutanoyl]oxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl] octanoate
IUPAC Name	[(2S,3R,4S,5R,6S)-6-[(2S,3S,4R,5R,6S)-6-[[(1R,3S,5S,6R,7R,8R,20S,22R,24R,25S,26S)-26-acetyloxy-7,25-dihydroxy-5,24-dimethyl-10-oxo-20-pentyl-2,4,9,21,23-pentaoxatricyclo[20.4.0.03,8]hexacosan-6-yl]oxy]-2-methyl-5-[(2S)-2-methylbutanoyl]oxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl] octanoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	118716651
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 190195 0 0 0 0 0 0 0 0999 V2000 19.4249 -15.3874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.0154 -14.8744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.6059 -14.3614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.1963 -13.8483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7868 -13.3353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3772 -12.8223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9677 -12.3092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5582 -11.7962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4091 -12.7604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2977 -10.3190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8882 -9.8060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3882 -9.8060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6382 -8.5069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3882 -7.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8882 -7.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6382 -8.5069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7872 -7.5427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6277 -5.7307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 -6.6949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7181 -5.2176 0.0000 C 0 0 0 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C 0 0 0 0 0 0 0 0 0 0 0 0 4.9030 1.7784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9388 2.9275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 -2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 -0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0586 -1.4772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7981 -2.9544 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5586 -1.4772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9681 -0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1172 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8672 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1277 2.7762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8672 4.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1172 5.5525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9681 6.5167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5586 7.0297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0586 7.0297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 6.5167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 5.5525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 4.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 4.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 5.5525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 6.8515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 6.8515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4895 8.3287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 6.5167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 3.7404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3086 4.7046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3934 5.9166 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7181 4.1916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0292 8.1208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9999 9.2118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9705 10.3029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0588 11.3940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0882 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0 0 0 0 0 0 -0.9449 7.8902 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0586 6.0037 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1277 3.6786 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2312 5.6011 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8793 2.9481 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1203 9.1501 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8208 7.2321 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0909 10.2412 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0424 8.0571 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0616 11.3323 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2379 9.4142 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0322 12.4233 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1499 10.3646 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1176 13.5761 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1793 11.4557 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0029 13.5144 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7981 1.9284 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4660 -0.2938 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6849 2.1132 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0105 -7.6590 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1237 -7.8439 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1954 -5.5458 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9091 -12.7604 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1714 -11.5436 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1466 -11.2047 0.0000 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 2 0 8 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 15 18 1 0 14 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 31 33 1 0 30 34 1 0 29 35 1 0 28 36 1 0 24 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 23 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 49 52 1 0 52 53 1 0 53 54 2 0 53 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 67 69 1 0 69 70 1 0 70 71 1 0 71 72 1 0 71 73 1 0 70 74 1 0 69 75 1 0 75 76 1 0 76 77 2 0 76 78 1 0 64 79 1 0 79 80 1 0 80 81 1 0 81 82 1 0 82 83 1 0 46 84 1 0 21 85 1 0 12 86 1 0 16 11 1 0 25 20 1 0 32 27 1 0 50 45 1 0 68 48 1 0 72 66 1 0 1 87 1 0 1 88 1 0 1 89 1 0 2 90 1 0 2 91 1 0 3 92 1 0 3 93 1 0 4 94 1 0 4 95 1 0 5 96 1 0 5 97 1 0 6 98 1 0 6 99 1 0 7100 1 0 7101 1 0 11102 1 6 12103 1 1 14104 1 6 15105 1 1 16106 1 1 17107 1 0 18108 1 0 20109 1 6 21110 1 1 23111 1 6 24112 1 1 25113 1 1 27114 1 1 28115 1 6 29116 1 6 30117 1 1 31118 1 6 33119 1 0 33120 1 0 33121 1 0 34122 1 0 35123 1 0 36124 1 0 40125 1 1 41126 1 0 41127 1 0 41128 1 0 42129 1 0 42130 1 0 43131 1 0 43132 1 0 43133 1 0 45134 1 1 46135 1 6 48136 1 1 49137 1 6 50138 1 6 51139 1 0 55140 1 0 55141 1 0 56142 1 0 56143 1 0 57144 1 0 57145 1 0 58146 1 0 58147 1 0 59148 1 0 59149 1 0 60150 1 0 60151 1 0 61152 1 0 61153 1 0 62154 1 0 62155 1 0 63156 1 0 63157 1 0 64158 1 1 66159 1 1 67160 1 6 69161 1 1 70162 1 1 71163 1 1 73164 1 0 73165 1 0 73166 1 0 74167 1 0 78168 1 0 78169 1 0 78170 1 0 79171 1 0 79172 1 0 80173 1 0 80174 1 0 81175 1 0 81176 1 0 82177 1 0 82178 1 0 83179 1 0 83180 1 0 83181 1 0 84182 1 0 84183 1 0 84184 1 0 85185 1 0 85186 1 0 85187 1 0 86188 1 0 86189 1 0 86190 1 0 M END

Standard InCHIKey	ULHBQMNMEGBFKP-ZEBKWYSNSA-N
Standard InCHI	InChI=1S/C61H104O25/c1-11-14-16-20-25-29-39(63)80-48-34(7)75-58(46(70)44(48)68)84-50-36(9)77-61(55(82-56(72)31(4)13-3)53(50)85-57-45(69)43(67)41(65)32(5)73-57)83-49-35(8)76-59-52(47(49)71)81-40(64)30-26-22-19-17-18-21-24-28-38(27-23-15-12-2)79-60-54(86-59)51(78-37(10)62)42(66)33(6)74-60/h31-36,38,41-55,57-61,65-71H,11-30H2,1-10H3/t31-,32-,33+,34-,35-,36-,38-,41-,42-,43+,44-,45+,46+,47+,48-,49-,50-,51-,52+,53+,54+,55+,57-,58-,59-,60-,61-/m0/s1
SMILES	CCCCCCCC(=O)O[C@H]1[C@@H](O[C@H]([C@@H]([C@@H]1O)O)O[C@H]2[C@@H](O[C@H]([C@@H]([C@@H]2O[C@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)C)O)O)O)OC(=O)[C@@H](C)CC)O[C@H]4[C@@H](O[C@@H]5[C@@H]([C@@H]4O)OC(=O)CCCCCCCCC[C@@H](O[C@H]6[C@H](O5)[C@H]([C@H]([C@H](O6)C)O)OC(=O)C)CCCCC)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1236.69	Volume:	1221.483 ? Van der Waals volume.
Dense:	1.012	LogP:	4.199 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.095 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.84 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	24.0	Rigid Bonds:	50.0
TPSA:	339.11 ? Topological Polar Surface Area.	H-Bond Acceptor:	25.0
H-Bond Donor:	7.0	Rings:	6.0
Heavy Atoms:	25.0

MedChem Properties

QED Drug-Likeness Score:	0.048	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.378	Fsp³:	0.934
MCE-18:	127.068 ? 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:	0.999	Fluc inhibitor:	0.333 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.543	Promiscuous compounds:	0.128

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.591	MDCK Permeability:	-5.094
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.002	30% Bioavailability (F30%):	0.061
50% Bioavailability (F50%):	0.86

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	90.054%	Volume Distribution (VD):	-0.16
Fu:	6.169% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.781
OATP1B3 inhibitor:	0.86	BCRP inhibitor:	0.0
BSEP inhibitor:	0.465

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.367
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.991 ? 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):

0.657

Half-life (T1/2):

2.768

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.171
Human Hepatotoxicity (H-HT):	0.279	Drug-induced Liver Injury (DILI):	0.974
AMES Toxicity:	0.51	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.0	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.615	Drug-induced Nephrotoxicity:	0.966
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.542
A549 Cytotoxicity:	0.965	Hek293 Cytotoxicity:	0.138
BCF:	0.214 ? 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:	3.883 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.869 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.539 ? 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
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	Whole Plant	Dongshan, Nanjing, Jiangsu Province, China	2012-NOV	PMID[25314138]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38192648]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

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	4
Others	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1045	Cell line	U2OS	Homo sapiens	IC50	=	5600	nM	PMID[25314138]
NPT659	Cell line	SMMC-7721	Homo sapiens	IC50	=	7800	nM	PMID[25314138]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	4500	nM	PMID[25314138]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	5500	nM	PMID[25314138]
NPT2	Others	Unspecified	n.a.	IC50	=	5400	nM	PMID[25314138]
NPT2	Others	Unspecified	n.a.	IC50	=	5600	nM	PMID[25314138]

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 NPC477318 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	22373
0.1-0.2	24242
0.2-0.3	2989
0.3-0.4	124
0.4-0.5	17
0.5-0.6	49
0.6-0.7	46
0.7-0.8	0
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477317
0.8795	High Similarity	NPC472200
0.8537	High Similarity	NPC119583
0.8333	Intermediate Similarity	NPC115013
0.8148	Intermediate Similarity	NPC89843
0.8023	Intermediate Similarity	NPC184915
0.8	Intermediate Similarity	NPC483170
0.7841	Intermediate Similarity	NPC44782
0.7816	Intermediate Similarity	NPC224953
0.7701	Intermediate Similarity	NPC169345
0.7558	Intermediate Similarity	NPC477319
0.7471	Intermediate Similarity	NPC143421
0.7303	Intermediate Similarity	NPC290012
0.7273	Intermediate Similarity	NPC307400
0.7273	Intermediate Similarity	NPC27289
0.7126	Intermediate Similarity	NPC109887
0.7045	Intermediate Similarity	NPC146992
0.7045	Intermediate Similarity	NPC85759
0.6957	Remote Similarity	NPC123204
0.6889	Remote Similarity	NPC294748
0.6848	Remote Similarity	NPC259294
0.6848	Remote Similarity	NPC126685
0.6739	Remote Similarity	NPC238056
0.6705	Remote Similarity	NPC478734
0.6703	Remote Similarity	NPC472204
0.6667	Remote Similarity	NPC183888
0.6667	Remote Similarity	NPC22742
0.6667	Remote Similarity	NPC113745
0.6667	Remote Similarity	NPC267592
0.6667	Remote Similarity	NPC477346
0.6667	Remote Similarity	NPC477320
0.6667	Remote Similarity	NPC477323
0.6667	Remote Similarity	NPC477325
0.6667	Remote Similarity	NPC609436
0.6628	Remote Similarity	NPC281563
0.6556	Remote Similarity	NPC478733
0.6526	Remote Similarity	NPC269318
0.6444	Remote Similarity	NPC477344
0.6413	Remote Similarity	NPC297768
0.6408	Remote Similarity	NPC10883
0.6333	Remote Similarity	NPC477331
0.6304	Remote Similarity	NPC478722
0.6277	Remote Similarity	NPC238264
0.6277	Remote Similarity	NPC476087
0.6277	Remote Similarity	NPC475667
0.6277	Remote Similarity	NPC477345
0.6264	Remote Similarity	NPC479059
0.6264	Remote Similarity	NPC600446
0.6264	Remote Similarity	NPC605013
0.6237	Remote Similarity	NPC173328
0.6235	Remote Similarity	NPC606819
0.6211	Remote Similarity	NPC478732
0.6207	Remote Similarity	NPC146380
0.6146	Remote Similarity	NPC475270
0.6146	Remote Similarity	NPC475327
0.6105	Remote Similarity	NPC478726
0.61	Remote Similarity	NPC475241
0.6095	Remote Similarity	NPC10121
0.6095	Remote Similarity	NPC198918
0.6087	Remote Similarity	NPC158302
0.6087	Remote Similarity	NPC477326
0.6082	Remote Similarity	NPC163409
0.6055	Remote Similarity	NPC472352
0.6	Remote Similarity	NPC186992
0.596	Remote Similarity	NPC475164
0.5957	Remote Similarity	NPC479061
0.5955	Remote Similarity	NPC477328
0.5943	Remote Similarity	NPC290276
0.5895	Remote Similarity	NPC479060
0.5889	Remote Similarity	NPC477329
0.587	Remote Similarity	NPC604005
0.587	Remote Similarity	NPC605014
0.5865	Remote Similarity	NPC63404
0.5862	Remote Similarity	NPC478729
0.5794	Remote Similarity	NPC611287
0.5778	Remote Similarity	NPC477330
0.5743	Remote Similarity	NPC473605
0.5743	Remote Similarity	NPC475375
0.573	Remote Similarity	NPC477350
0.5729	Remote Similarity	NPC472205
0.5729	Remote Similarity	NPC478723
0.5729	Remote Similarity	NPC478724
0.5726	Remote Similarity	NPC147032
0.5714	Remote Similarity	NPC35338
0.5714	Remote Similarity	NPC204214
0.5714	Remote Similarity	NPC92283
0.567	Remote Similarity	NPC478730
0.5664	Remote Similarity	NPC471024
0.566	Remote Similarity	NPC28069
0.5644	Remote Similarity	NPC478728
0.5638	Remote Similarity	NPC477332
0.5625	Remote Similarity	NPC60849
0.5625	Remote Similarity	NPC478725
0.5596	Remote Similarity	NPC610996
0.5588	Remote Similarity	NPC478727
0.5567	Remote Similarity	NPC479058
0.5514	Remote Similarity	NPC77651
0.55	Remote Similarity	NPC479057
0.5455	Remote Similarity	NPC600672
0.5446	Remote Similarity	NPC475525
0.5446	Remote Similarity	NPC475540
0.5426	Remote Similarity	NPC477349
0.5408	Remote Similarity	NPC44682
0.54	Remote Similarity	NPC478731
0.5398	Remote Similarity	NPC600940
0.5392	Remote Similarity	NPC476066
0.5327	Remote Similarity	NPC124878
0.5327	Remote Similarity	NPC231888
0.5268	Remote Similarity	NPC471025
0.5263	Remote Similarity	NPC610997
0.5221	Remote Similarity	NPC600721
0.5221	Remote Similarity	NPC605872
0.5086	Remote Similarity	NPC471026

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477318 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7288
0.1-0.2	1795
0.2-0.3	65
0.3-0.4	2
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