NPASS Compound

Natural Product: NPC1046

Natural Product ID	NPC1046
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Asterlingulatoside A
IUPAC Name	[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL498836
PubChem CID	10533197
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 120126 0 0 0 0 0 0 0 0999 V2000 -5.1687 -3.4923 2.0763 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9243 -3.5258 0.6138 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0621 -4.9774 0.1309 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9352 -2.7390 -0.1885 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2209 -1.7806 -1.1528 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4202 -0.8541 -0.3246 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4210 -1.6259 0.5190 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5101 -3.1039 0.2191 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0600 -1.0676 0.4121 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4293 -0.7466 1.5192 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0748 -0.1759 1.6576 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6313 -0.4017 0.3465 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0180 0.1159 0.4622 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1510 1.2647 1.4299 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8326 -1.0123 1.1349 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2585 -0.6238 1.3281 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9481 0.0032 0.1584 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1121 0.7422 -0.8040 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2344 2.2604 -0.6668 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6487 0.4389 -2.2010 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6741 0.3001 -0.8413 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8475 1.0304 -1.8548 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6189 0.1577 -2.0182 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2156 0.0868 -0.7640 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7473 1.5007 -0.5703 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3885 -0.8616 -0.9298 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0059 -2.2419 -1.3939 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4825 -0.3506 -1.8298 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6689 0.1977 -1.0661 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4836 0.8045 -2.0561 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8847 0.8938 0.7101 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1961 0.4986 0.5312 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9502 1.5927 -0.1790 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3272 1.0147 -0.5216 C 0 0 2 0 0 0 0 0 0 0 0 0 9.9792 0.3282 0.6304 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9984 -0.3936 1.5242 C 0 0 1 0 0 0 0 0 0 0 0 0 9.7286 -0.7288 2.8250 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8631 -1.4482 2.4796 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8526 0.3240 1.7584 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8639 -0.6270 0.1309 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1480 1.9781 -1.0744 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3714 1.9851 -1.3630 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3809 -0.1114 0.5716 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2356 -0.2224 1.8293 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3973 0.6730 0.1287 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3013 1.3706 0.9681 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2335 2.8455 0.8339 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2316 3.4629 -0.0992 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.5687 2.7387 -0.0451 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2380 1.2634 -0.2990 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5491 0.8237 0.8060 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3997 3.2670 -1.0003 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7401 3.5215 -1.3950 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4704 3.4148 2.1027 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4732 -4.4960 2.4341 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2061 -3.2744 2.5973 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9828 -2.8032 2.3846 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4718 -5.1148 -0.7996 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7367 -5.6953 0.8953 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1262 -5.1942 -0.1415 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5565 -2.0848 0.4615 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5922 -3.3658 -0.8152 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7193 -2.2860 -1.9675 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0605 -1.1812 -1.6121 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7988 -1.5702 1.5621 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8428 -3.6486 0.9161 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4254 -3.3684 -0.8257 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9834 -0.9263 2.4836 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4508 -0.6924 2.4998 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2050 0.9081 1.8841 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7112 -1.5210 0.1659 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5750 2.1535 1.2037 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2059 1.5883 1.5600 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8433 0.9494 2.4702 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7289 -1.9388 0.5406 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3924 -1.1759 2.1378 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8011 -1.5476 1.6215 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3188 0.0246 2.2478 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5844 -0.7968 -0.3266 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2431 2.7408 -0.5363 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9490 2.5179 0.1572 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6684 2.7379 -1.5700 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0301 -0.3114 -2.7391 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6630 -0.0133 -2.1495 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6481 1.3410 -2.8588 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7495 -0.7457 -1.2860 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6924 2.0757 -1.7192 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4043 0.9153 -2.8344 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0660 0.5825 -2.8764 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0966 -0.8320 -2.2867 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2817 1.6579 0.3744 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4020 1.7487 -1.4590 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0284 2.2719 -0.6064 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0753 -3.0087 -0.5606 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6661 -2.5824 -2.2528 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0062 -2.3796 -1.7839 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9419 -1.2201 -2.4081 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1436 0.3029 -2.6467 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4381 0.9953 -0.3611 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1174 1.6878 -2.3045 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3324 -0.4319 -0.0230 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1261 2.4754 0.4707 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1277 0.2474 -1.3083 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5873 1.0692 1.1953 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7311 -1.3535 1.0555 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0470 -1.3980 3.3816 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9769 0.1997 3.3864 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7001 -0.9839 2.7804 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5428 -0.2572 -0.4760 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6322 2.4094 -0.3187 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0394 2.0213 -2.1165 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9784 1.1177 2.0232 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2234 3.1884 0.5357 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4200 4.5053 0.2306 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9503 2.7921 0.9874 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5851 1.2497 -1.1805 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1542 0.6609 -0.4114 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1615 4.2227 -1.1274 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9261 4.1006 -1.3539 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2157 2.9532 2.5755 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 24 26 1 0 26 27 1 6 26 28 1 0 28 29 1 0 29 30 1 0 17 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 35 40 1 0 34 41 1 0 33 42 1 0 6 43 1 1 43 44 2 0 43 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 48 53 1 0 47 54 1 0 8 2 1 0 26 9 1 0 39 32 1 0 51 46 1 0 29 6 1 0 24 12 1 0 21 13 1 0 1 55 1 0 1 56 1 0 1 57 1 0 3 58 1 0 3 59 1 0 3 60 1 0 4 61 1 0 4 62 1 0 5 63 1 0 5 64 1 0 7 65 1 1 8 66 1 0 8 67 1 0 10 68 1 0 11 69 1 0 11 70 1 0 12 71 1 6 14 72 1 0 14 73 1 0 14 74 1 0 15 75 1 0 15 76 1 0 16 77 1 0 16 78 1 0 17 79 1 6 19 80 1 0 19 81 1 0 19 82 1 0 20 83 1 0 20 84 1 0 20 85 1 0 21 86 1 6 22 87 1 0 22 88 1 0 23 89 1 0 23 90 1 0 25 91 1 0 25 92 1 0 25 93 1 0 27 94 1 0 27 95 1 0 27 96 1 0 28 97 1 0 28 98 1 0 29 99 1 1 30100 1 0 32101 1 6 33102 1 1 34103 1 6 35104 1 1 36105 1 6 37106 1 0 37107 1 0 38108 1 0 40109 1 0 41110 1 0 42111 1 0 46112 1 1 47113 1 6 48114 1 1 49115 1 1 50116 1 0 50117 1 0 52118 1 0 53119 1 0 54120 1 0 M END

Standard InCHIKey	TXWNGCHVKNRKBJ-JYTHRGSDSA-N
Standard InCHI	InChI=1S/C41H66O13/c1-36(2)14-15-41(35(50)54-33-31(48)28(45)22(43)19-51-33)21(16-36)20-8-9-25-38(5)12-11-27(53-34-32(49)30(47)29(46)23(18-42)52-34)37(3,4)24(38)10-13-39(25,6)40(20,7)17-26(41)44/h8,21-34,42-49H,9-19H2,1-7H3/t21-,22-,23+,24-,25+,26+,27-,28-,29+,30-,31+,32+,33-,34-,38-,39+,40+,41+/m0/s1
SMILES	CC1(C)CC[C@]2([C@@H](C1)C1=CC[C@@H]3[C@@]4(C)CC[C@@H](C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)C[C@H]2O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	766.45	Volume:	766.797 ? Van der Waals volume.
Dense:	1.0	LogP:	2.664 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.974 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.476 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	39.0
TPSA:	215.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	8.0	Rings:	7.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.114	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.819	Fsp³:	0.927
MCE-18:	151.772 ? 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:	0.844	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.173	Promiscuous compounds:	0.076

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.994	MDCK Permeability:	-5.121
Pgp-inhibitor:	0.003	Pgp-substrate:	0.037
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):	0.037
20% Bioavailability (F20%):	0.521	30% Bioavailability (F30%):	0.983
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.17	MRP1:	0.141
Plasma Protein Binding (PPB):	76.931%	Volume Distribution (VD):	-0.431
Fu:	15.678% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.028
BSEP inhibitor:	0.009

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.037
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.98
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.318
HLM stability:	0.699 ? 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):

0.503

Half-life (T1/2):

2.077

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.018
Human Hepatotoxicity (H-HT):	0.845	Drug-induced Liver Injury (DILI):	0.935
AMES Toxicity:	0.948	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.016	Skin Sensitization:	1.0
Carcinogencity:	0.496	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.035
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.99
Hematotoxicity:	0.726	Drug-induced Nephrotoxicity:	0.995
Genotoxicity:	0.748	RPMI-8226 Immunitoxicity:	0.152
A549 Cytotoxicity:	0.914	Hek293 Cytotoxicity:	0.449
BCF:	1.765 ? 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:	3.782 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.267 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.492 ? 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
NPO26359	Aster lingulatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9249983]
NPO26359	Aster lingulatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26359	Aster lingulatus	Species	Asteraceae	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	1

Activity Type	# Activity
Cell line	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
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	39000.0	nM	PMID[3839258]

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 NPC1046 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	19643
0.1-0.2	24349
0.2-0.3	4232
0.3-0.4	959
0.4-0.5	400
0.5-0.6	111
0.6-0.7	74
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8152	Intermediate Similarity	NPC164389
0.7938	Intermediate Similarity	NPC104137
0.7938	Intermediate Similarity	NPC26626
0.7857	Intermediate Similarity	NPC11242
0.7451	Intermediate Similarity	NPC123522
0.7404	Intermediate Similarity	NPC283417
0.7404	Intermediate Similarity	NPC200049
0.7347	Intermediate Similarity	NPC64715
0.7264	Intermediate Similarity	NPC4749
0.7264	Intermediate Similarity	NPC85154
0.7234	Intermediate Similarity	NPC480420
0.7216	Intermediate Similarity	NPC488526
0.713	Intermediate Similarity	NPC286457
0.7037	Intermediate Similarity	NPC21691
0.6939	Remote Similarity	NPC117714
0.6939	Remote Similarity	NPC30289
0.6915	Remote Similarity	NPC475208
0.6909	Remote Similarity	NPC470876
0.6907	Remote Similarity	NPC469946
0.6882	Remote Similarity	NPC90856
0.6882	Remote Similarity	NPC214484
0.6875	Remote Similarity	NPC302543
0.6804	Remote Similarity	NPC39211
0.6771	Remote Similarity	NPC475516
0.6737	Remote Similarity	NPC48499
0.6607	Remote Similarity	NPC475514
0.6571	Remote Similarity	NPC207738
0.6569	Remote Similarity	NPC297263
0.6566	Remote Similarity	NPC263756
0.6566	Remote Similarity	NPC213674
0.6559	Remote Similarity	NPC128925
0.6538	Remote Similarity	NPC481079
0.6535	Remote Similarity	NPC305267
0.6526	Remote Similarity	NPC204458
0.6526	Remote Similarity	NPC238935
0.6518	Remote Similarity	NPC473452
0.6509	Remote Similarity	NPC815
0.65	Remote Similarity	NPC112352
0.6471	Remote Similarity	NPC33012
0.6471	Remote Similarity	NPC488520
0.6466	Remote Similarity	NPC220160
0.6465	Remote Similarity	NPC295371
0.6441	Remote Similarity	NPC489209
0.6429	Remote Similarity	NPC235405
0.6415	Remote Similarity	NPC31838
0.6415	Remote Similarity	NPC187290
0.6413	Remote Similarity	NPC48249
0.64	Remote Similarity	NPC76497
0.6387	Remote Similarity	NPC8524
0.6381	Remote Similarity	NPC301449
0.6381	Remote Similarity	NPC601290
0.6373	Remote Similarity	NPC232237
0.6372	Remote Similarity	NPC13998
0.6364	Remote Similarity	NPC249848
0.6364	Remote Similarity	NPC107966
0.6337	Remote Similarity	NPC223301
0.6337	Remote Similarity	NPC171544
0.6322	Remote Similarity	NPC488522
0.6311	Remote Similarity	NPC105800
0.6311	Remote Similarity	NPC63159
0.6311	Remote Similarity	NPC235438
0.6289	Remote Similarity	NPC78046
0.6286	Remote Similarity	NPC104372
0.6262	Remote Similarity	NPC481078
0.6186	Remote Similarity	NPC482010
0.618	Remote Similarity	NPC488524
0.6168	Remote Similarity	NPC295823
0.6168	Remote Similarity	NPC174720
0.6168	Remote Similarity	NPC475467
0.6168	Remote Similarity	NPC69811
0.6154	Remote Similarity	NPC309223
0.6139	Remote Similarity	NPC157868
0.6129	Remote Similarity	NPC489208
0.6117	Remote Similarity	NPC30735
0.6095	Remote Similarity	NPC222580
0.6091	Remote Similarity	NPC610204
0.6082	Remote Similarity	NPC161434
0.6058	Remote Similarity	NPC40775
0.6058	Remote Similarity	NPC44716
0.6058	Remote Similarity	NPC159309
0.6058	Remote Similarity	NPC46665
0.6058	Remote Similarity	NPC2370
0.6058	Remote Similarity	NPC86222
0.6053	Remote Similarity	NPC481080
0.6019	Remote Similarity	NPC192791
0.6	Remote Similarity	NPC475591
0.6	Remote Similarity	NPC236870
0.6	Remote Similarity	NPC185466
0.5978	Remote Similarity	NPC167383
0.595	Remote Similarity	NPC102505
0.595	Remote Similarity	NPC488514
0.5929	Remote Similarity	NPC123199
0.5905	Remote Similarity	NPC10607
0.5905	Remote Similarity	NPC251768
0.5882	Remote Similarity	NPC173583
0.5876	Remote Similarity	NPC256798
0.5872	Remote Similarity	NPC80986
0.5859	Remote Similarity	NPC189884
0.5859	Remote Similarity	NPC138334
0.5851	Remote Similarity	NPC237503
0.5846	Remote Similarity	NPC475394
0.5833	Remote Similarity	NPC281148
0.5833	Remote Similarity	NPC31839
0.5833	Remote Similarity	NPC114484
0.5812	Remote Similarity	NPC265841
0.5789	Remote Similarity	NPC603137
0.5773	Remote Similarity	NPC242611
0.5758	Remote Similarity	NPC475584
0.5758	Remote Similarity	NPC475152
0.5755	Remote Similarity	NPC480475
0.5752	Remote Similarity	NPC79643
0.5741	Remote Similarity	NPC302887
0.5739	Remote Similarity	NPC480423
0.5739	Remote Similarity	NPC602995
0.5728	Remote Similarity	NPC58448
0.5727	Remote Similarity	NPC160452
0.5726	Remote Similarity	NPC57484
0.569	Remote Similarity	NPC25663
0.569	Remote Similarity	NPC488560
0.5673	Remote Similarity	NPC488516
0.5667	Remote Similarity	NPC481081
0.5664	Remote Similarity	NPC610461
0.5662	Remote Similarity	NPC23020
0.5652	Remote Similarity	NPC135904
0.5636	Remote Similarity	NPC606145
0.5625	Remote Similarity	NPC606107
0.562	Remote Similarity	NPC144644
0.562	Remote Similarity	NPC37860
0.562	Remote Similarity	NPC170407
0.5619	Remote Similarity	NPC80843
0.5603	Remote Similarity	NPC475160
0.5603	Remote Similarity	NPC473714
0.5596	Remote Similarity	NPC471435
0.5596	Remote Similarity	NPC471434
0.5586	Remote Similarity	NPC241909
0.5546	Remote Similarity	NPC488308
0.5528	Remote Similarity	NPC142151
0.5528	Remote Similarity	NPC267694
0.5526	Remote Similarity	NPC475287
0.5526	Remote Similarity	NPC607904
0.5524	Remote Similarity	NPC473884
0.5517	Remote Similarity	NPC488519
0.5514	Remote Similarity	NPC160415
0.55	Remote Similarity	NPC271610
0.55	Remote Similarity	NPC312650
0.55	Remote Similarity	NPC209894
0.5495	Remote Similarity	NPC291903
0.549	Remote Similarity	NPC29069
0.5487	Remote Similarity	NPC210729
0.5487	Remote Similarity	NPC82931
0.5484	Remote Similarity	NPC250247
0.5481	Remote Similarity	NPC139894
0.547	Remote Similarity	NPC475140
0.5464	Remote Similarity	NPC283849
0.5462	Remote Similarity	NPC476068
0.5455	Remote Similarity	NPC79718
0.5447	Remote Similarity	NPC70809
0.5446	Remote Similarity	NPC470477
0.5446	Remote Similarity	NPC195132
0.544	Remote Similarity	NPC68767
0.544	Remote Similarity	NPC293031
0.5439	Remote Similarity	NPC172365
0.5439	Remote Similarity	NPC288205
0.5439	Remote Similarity	NPC51465
0.5437	Remote Similarity	NPC179434
0.5435	Remote Similarity	NPC86368
0.5429	Remote Similarity	NPC127056
0.5421	Remote Similarity	NPC242840
0.5421	Remote Similarity	NPC256133
0.5398	Remote Similarity	NPC609281
0.5397	Remote Similarity	NPC110385
0.5397	Remote Similarity	NPC153673
0.5397	Remote Similarity	NPC51099
0.5392	Remote Similarity	NPC473481
0.5391	Remote Similarity	NPC60557
0.5391	Remote Similarity	NPC473824
0.5391	Remote Similarity	NPC67857
0.5385	Remote Similarity	NPC475177
0.5379	Remote Similarity	NPC484831
0.5379	Remote Similarity	NPC484830
0.5377	Remote Similarity	NPC488561
0.5372	Remote Similarity	NPC41061
0.5372	Remote Similarity	NPC227551
0.537	Remote Similarity	NPC605226
0.5366	Remote Similarity	NPC476991
0.5364	Remote Similarity	NPC475504
0.5364	Remote Similarity	NPC123796
0.5364	Remote Similarity	NPC488517
0.5339	Remote Similarity	NPC470218
0.5315	Remote Similarity	NPC488515
0.531	Remote Similarity	NPC480473
0.531	Remote Similarity	NPC480474
0.531	Remote Similarity	NPC477193
0.5304	Remote Similarity	NPC25998
0.5304	Remote Similarity	NPC475119
0.5294	Remote Similarity	NPC480951
0.5285	Remote Similarity	NPC236638
0.5285	Remote Similarity	NPC294453
0.5285	Remote Similarity	NPC305981

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC1046 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6986
0.1-0.2	2090
0.2-0.3	65
0.3-0.4	8
0.4-0.5	1
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