NPASS Compound

Natural Product: NPC477451

Natural Product ID	NPC477451
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2S,3S,4R,5R,6R)-2-[(2R,3S,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
IUPAC Name	(2S,3S,4R,5R,6R)-2-[(2R,3S,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	76327917
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal 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 115122 0 0 0 0 0 0 0 0999 V2000 11.6459 0.1951 -0.5913 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4701 1.1097 -0.7565 C 0 0 2 0 0 0 0 0 0 0 0 0 9.6331 1.0168 0.5124 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4496 0.0820 0.2375 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5849 0.7685 -0.7974 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6651 1.7236 -0.0386 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3552 1.4934 -0.7003 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6424 0.5782 -1.8909 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7700 -0.0930 -1.4890 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4255 -0.3365 -2.0200 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4609 0.2198 -1.0358 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3812 0.6744 0.0844 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5191 1.4745 1.0219 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4061 0.6560 1.5718 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5833 0.0065 0.4943 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4100 -0.7128 -0.5457 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5174 -1.1257 -1.6892 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0820 -0.7279 -1.4655 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4665 -1.1215 -0.1399 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5219 -0.8966 1.0118 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2211 -0.3109 2.2070 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 -1.1225 2.3345 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4457 -0.5250 1.3134 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7074 -0.2495 0.0666 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5917 -1.2787 1.1590 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7610 -0.7029 1.5632 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7654 -0.8167 0.4348 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5561 -2.1752 -0.1989 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1820 -3.1695 0.8473 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5098 -2.7911 2.2506 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2695 -1.4880 2.6004 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9188 -3.2290 2.6480 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1516 -4.5545 2.2937 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9047 -4.3495 0.5453 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4725 -2.0539 -1.0977 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6501 0.2026 -0.5073 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8394 0.8804 -0.5970 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7195 2.3705 -0.2754 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1271 2.8147 0.0740 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0567 2.4473 -1.0439 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7866 1.1129 -1.6649 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4375 0.8345 -1.8572 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4929 1.0396 -3.0007 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0974 3.4226 -2.0462 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4861 2.0908 1.2231 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4166 3.0290 -1.4908 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0213 -2.2495 1.4750 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0010 -0.4623 0.8212 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0871 3.1651 -0.3121 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3640 1.4483 -1.7332 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5797 0.7611 -1.9062 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4063 0.7642 0.0185 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0997 -0.1413 -1.5317 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3189 -0.6566 0.0640 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7648 2.1846 -0.8923 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1899 0.6062 1.3613 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2083 1.9942 0.8050 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7976 -0.9152 -0.1045 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9303 -0.0303 1.2067 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6868 1.5508 1.0414 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8525 2.4177 -1.0482 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7820 1.1793 -2.8230 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6695 -1.3910 -1.9093 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0066 -0.1904 -3.0533 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9662 1.1105 -1.4728 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1203 2.3851 0.5639 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1595 1.7906 1.8873 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7323 1.3686 2.1068 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7282 -0.0793 2.3526 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0661 0.8411 -0.0501 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8978 -1.6251 -0.1665 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6114 -2.2166 -1.9322 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8477 -0.6074 -2.6131 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0096 0.3503 -1.7079 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5049 -1.2554 -2.2745 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7540 -2.2007 -0.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3602 -0.4288 3.1379 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5089 0.7264 2.0729 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3523 -2.1968 2.1899 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9359 -0.9772 3.3598 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7694 0.4533 1.7584 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3027 -0.3783 -0.8745 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3194 0.8097 0.0151 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6618 0.3138 1.9653 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7898 -0.8095 0.8638 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4707 -2.4592 -0.7615 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1066 -3.5118 0.7661 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8356 -3.4165 2.9106 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0379 -3.1878 3.7592 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6907 -2.6279 2.1296 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4271 -5.0882 2.7143 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4219 -4.9108 -0.1079 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8048 -1.9466 -2.0281 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6048 0.4465 0.1121 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9833 2.5853 0.4969 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2036 3.9060 0.2431 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0784 2.3719 -0.5808 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1618 0.2847 -0.9984 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3881 1.7112 -2.9966 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7712 1.3019 -3.8010 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8741 0.0092 -3.1499 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9018 3.9957 -1.9158 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4336 2.2161 1.4702 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8884 2.6394 -2.2437 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7032 -3.0643 0.7896 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6322 -2.5447 2.4774 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1409 -2.2601 1.6125 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5785 -0.0378 1.6716 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1840 -1.0531 1.3039 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5668 -1.1635 0.2018 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1895 3.7455 0.6352 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3293 3.6955 -0.9245 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0343 3.1873 -0.9156 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3818 -0.3234 -2.0158 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0014 1.1240 -2.8816 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 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 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 23 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 30 32 1 0 32 33 1 0 29 34 1 0 28 35 1 0 27 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 41 43 1 0 40 44 1 0 39 45 1 0 38 46 1 0 20 47 1 1 12 48 1 1 6 49 1 0 5 50 1 6 50 51 1 0 51 2 1 0 9 5 1 0 12 7 1 0 16 11 1 0 20 15 1 0 24 19 1 0 31 26 1 0 42 37 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 6 3 56 1 0 3 57 1 0 4 58 1 0 4 59 1 0 6 60 1 1 7 61 1 6 8 62 1 6 10 63 1 0 10 64 1 0 11 65 1 6 13 66 1 0 13 67 1 0 14 68 1 0 14 69 1 0 15 70 1 6 16 71 1 1 17 72 1 0 17 73 1 0 18 74 1 0 18 75 1 0 19 76 1 6 21 77 1 0 21 78 1 0 22 79 1 0 22 80 1 0 23 81 1 1 24 82 1 0 24 83 1 0 26 84 1 1 27 85 1 1 28 86 1 6 29 87 1 1 30 88 1 1 32 89 1 0 32 90 1 0 33 91 1 0 34 92 1 0 35 93 1 0 37 94 1 1 38 95 1 1 39 96 1 1 40 97 1 1 41 98 1 1 43 99 1 0 43100 1 0 43101 1 0 44102 1 0 45103 1 0 46104 1 0 47105 1 0 47106 1 0 47107 1 0 48108 1 0 48109 1 0 48110 1 0 49111 1 0 49112 1 0 49113 1 0 51114 1 0 51115 1 0 M END

Standard InCHIKey	GJVMWJXVJKLODQ-GTAJWJONSA-N
Standard InCHI	InChI=1S/C39H64O12/c1-18-8-13-39(46-17-18)19(2)28-26(51-39)15-25-23-7-6-21-14-22(9-11-37(21,4)24(23)10-12-38(25,28)5)48-36-34(32(44)30(42)27(16-40)49-36)50-35-33(45)31(43)29(41)20(3)47-35/h18-36,40-45H,6-17H2,1-5H3/t18-,19+,20-,21-,22+,23-,24+,25+,26+,27+,28+,29+,30-,31-,32+,33+,34+,35+,36-,37+,38+,39-/m1/s1
SMILES	C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@H]6[C@@]5(CC[C@@H](C6)O[C@H]7[C@H]([C@H]([C@@H]([C@@H](O7)CO)O)O)O[C@H]8[C@H]([C@@H]([C@H]([C@H](O8)C)O)O)O)C)C)C)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	724.44	Volume:	720.131 ? Van der Waals volume.
Dense:	1.006	LogP:	3.727 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.042 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.381 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	42.0
TPSA:	176.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	8.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.229	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.19	Fsp³:	1.0
MCE-18:	200.0 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.795	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.03 ? 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:	0.243	Promiscuous compounds:	0.033

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.292	MDCK Permeability:	-5.061
Pgp-inhibitor:	0.006	Pgp-substrate:	0.863
PAMPA:	0.999 ? 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):	0.009
20% Bioavailability (F20%):	0.818	30% Bioavailability (F30%):	0.871
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.75
Plasma Protein Binding (PPB):	70.314%	Volume Distribution (VD):	-0.324
Fu:	23.942% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.19
BSEP inhibitor:	0.47

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.223	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.997	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.992
HLM stability:	0.523 ? 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):

1.106

Half-life (T1/2):

1.844

ADMET: Toxicity

hERG Blockers:	0.036	hERG Blockers (10um):	0.167
Human Hepatotoxicity (H-HT):	0.463	Drug-induced Liver Injury (DILI):	0.967
AMES Toxicity:	0.942	Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.064	Skin Sensitization:	1.0
Carcinogencity:	0.299	Eye Corrosion:	0.0
Eye Irritation:	0.014	Respiratory Toxicity:	0.028
Drug-induced Neurotoxicity:	0.012	Ototoxicity:	0.987
Hematotoxicity:	0.455	Drug-induced Nephrotoxicity:	0.809
Genotoxicity:	0.004	RPMI-8226 Immunitoxicity:	0.283
A549 Cytotoxicity:	0.976	Hek293 Cytotoxicity:	0.955
BCF:	2.091 ? 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:	3.636 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.645 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.207 ? 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
NPO28342	Lilium candidum	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14980692]
NPO28342	Lilium candidum	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28342	Lilium candidum	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28342	Lilium candidum	Species	Liliaceae	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
EC50	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
NPT759	Cell line	H9	Homo sapiens	EC50	<	0.25	ug/ml	PMID[14980692]

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 NPC477451 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	27836
0.1-0.2	18742
0.2-0.3	2480
0.3-0.4	541
0.4-0.5	122
0.5-0.6	62
0.6-0.7	45
0.7-0.8	1
0.8-0.85	5
0.85-0.9	0
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9481	High Similarity	NPC297348
0.9481	High Similarity	NPC249204
0.9481	High Similarity	NPC48339
0.9481	High Similarity	NPC141769
0.9481	High Similarity	NPC477547
0.8471	Intermediate Similarity	NPC107962
0.8452	Intermediate Similarity	NPC211354
0.8372	Intermediate Similarity	NPC6295
0.8235	Intermediate Similarity	NPC19400
0.8214	Intermediate Similarity	NPC222731
0.7778	Intermediate Similarity	NPC113044
0.7778	Intermediate Similarity	NPC283829
0.7778	Intermediate Similarity	NPC161676
0.7765	Intermediate Similarity	NPC294686
0.7701	Intermediate Similarity	NPC206003
0.7701	Intermediate Similarity	NPC473610
0.7582	Intermediate Similarity	NPC160426
0.7558	Intermediate Similarity	NPC234352
0.7442	Intermediate Similarity	NPC325828
0.7283	Intermediate Similarity	NPC141433
0.7209	Intermediate Similarity	NPC485594
0.7174	Intermediate Similarity	NPC485595
0.7172	Intermediate Similarity	NPC475625
0.7128	Intermediate Similarity	NPC475351
0.7113	Intermediate Similarity	NPC128572
0.7083	Intermediate Similarity	NPC92890
0.7033	Intermediate Similarity	NPC107188
0.701	Intermediate Similarity	NPC471464
0.6915	Remote Similarity	NPC195297
0.6854	Remote Similarity	NPC177834
0.6813	Remote Similarity	NPC474399
0.6804	Remote Similarity	NPC475643
0.67	Remote Similarity	NPC184617
0.6667	Remote Similarity	NPC54619
0.6632	Remote Similarity	NPC125324
0.663	Remote Similarity	NPC250393
0.66	Remote Similarity	NPC480555
0.66	Remote Similarity	NPC150372
0.6593	Remote Similarity	NPC291203
0.6593	Remote Similarity	NPC217205
0.6566	Remote Similarity	NPC477809
0.6535	Remote Similarity	NPC97700
0.6535	Remote Similarity	NPC30856
0.6489	Remote Similarity	NPC306131
0.6489	Remote Similarity	NPC200802
0.6465	Remote Similarity	NPC470433
0.6465	Remote Similarity	NPC46190
0.6465	Remote Similarity	NPC171073
0.6337	Remote Similarity	NPC300557
0.63	Remote Similarity	NPC602423
0.6292	Remote Similarity	NPC473774
0.6292	Remote Similarity	NPC481419
0.6292	Remote Similarity	NPC481417
0.6262	Remote Similarity	NPC132080
0.6262	Remote Similarity	NPC480553
0.6226	Remote Similarity	NPC480554
0.6222	Remote Similarity	NPC24960
0.6211	Remote Similarity	NPC128123
0.6196	Remote Similarity	NPC181845
0.6176	Remote Similarity	NPC51172
0.6176	Remote Similarity	NPC49032
0.6162	Remote Similarity	NPC305423
0.6162	Remote Similarity	NPC14704
0.6132	Remote Similarity	NPC232037
0.6095	Remote Similarity	NPC269297
0.6095	Remote Similarity	NPC222202
0.6038	Remote Similarity	NPC475333
0.6038	Remote Similarity	NPC224098
0.6038	Remote Similarity	NPC208383
0.602	Remote Similarity	NPC485601
0.6019	Remote Similarity	NPC83137
0.6	Remote Similarity	NPC210157
0.6	Remote Similarity	NPC475319
0.596	Remote Similarity	NPC470432
0.596	Remote Similarity	NPC230507
0.5955	Remote Similarity	NPC144790
0.5955	Remote Similarity	NPC149400
0.5934	Remote Similarity	NPC481420
0.5934	Remote Similarity	NPC481421
0.5926	Remote Similarity	NPC470864
0.5922	Remote Similarity	NPC248746
0.59	Remote Similarity	NPC70204
0.5889	Remote Similarity	NPC277715
0.5888	Remote Similarity	NPC13193
0.5888	Remote Similarity	NPC116756
0.5882	Remote Similarity	NPC473601
0.5841	Remote Similarity	NPC480556
0.5833	Remote Similarity	NPC194207
0.5833	Remote Similarity	NPC22779
0.5758	Remote Similarity	NPC264101
0.57	Remote Similarity	NPC215408
0.5664	Remote Similarity	NPC470866
0.5596	Remote Similarity	NPC32361
0.5596	Remote Similarity	NPC309278
0.5577	Remote Similarity	NPC40440
0.5575	Remote Similarity	NPC232054
0.5567	Remote Similarity	NPC131693
0.5567	Remote Similarity	NPC475436
0.5566	Remote Similarity	NPC42171
0.5566	Remote Similarity	NPC274200
0.5556	Remote Similarity	NPC115165
0.5536	Remote Similarity	NPC233433
0.5517	Remote Similarity	NPC224314
0.544	Remote Similarity	NPC329807
0.5433	Remote Similarity	NPC481189
0.5429	Remote Similarity	NPC98696
0.5422	Remote Similarity	NPC248944
0.5422	Remote Similarity	NPC7479
0.5422	Remote Similarity	NPC257296
0.5421	Remote Similarity	NPC6806
0.5361	Remote Similarity	NPC481424
0.5361	Remote Similarity	NPC481422
0.5339	Remote Similarity	NPC220836
0.531	Remote Similarity	NPC476112
0.531	Remote Similarity	NPC307534
0.5271	Remote Similarity	NPC329727
0.5225	Remote Similarity	NPC475550
0.5221	Remote Similarity	NPC108072
0.5214	Remote Similarity	NPC94086
0.5214	Remote Similarity	NPC473817
0.521	Remote Similarity	NPC477808
0.5149	Remote Similarity	NPC292467
0.5143	Remote Similarity	NPC475670
0.514	Remote Similarity	NPC202898
0.513	Remote Similarity	NPC477811
0.5104	Remote Similarity	NPC481418
0.5098	Remote Similarity	NPC121453
0.5091	Remote Similarity	NPC151134
0.5059	Remote Similarity	NPC227260
0.5051	Remote Similarity	NPC481425
0.5051	Remote Similarity	NPC481426
0.5047	Remote Similarity	NPC112274
0.5045	Remote Similarity	NPC294129
0.5044	Remote Similarity	NPC473518
0.5043	Remote Similarity	NPC470862

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7734
0.1-0.2	1333
0.2-0.3	70
0.3-0.4	6
0.4-0.5	3
0.5-0.6	2
0.6-0.7	1
0.7-0.8	1
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
0.7442	Intermediate Similarity	NPD8171	Phase 2
0.6289	Remote Similarity	NPD8170	Phase 2
0.5422	Remote Similarity	NPD6928	Phase 2
0.5319	Remote Similarity	NPD7991	Discontinued

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