NPASS Compound

Natural Product: NPC476539

Natural Product ID	NPC476539
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Tropeoside A2
IUPAC Name	(2R,3S,4S,5S,6R)-2-[(2R)-4-[(1S,2S,4S,6S,7S,8R,9S,12S,13R,14R,16R)-6,16-dihydroxy-7,9,13-trimethyl-14-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-en-6-yl]-2-methylbutoxy]-6-methyloxane-3,4,5-triol
Synonyms	Tropeoside A2
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44566259
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 117123 0 0 0 0 0 0 0 0999 V2000 2.6614 0.1382 1.4118 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9738 -1.0959 0.8358 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9430 -0.6232 -0.1348 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5619 -0.9208 -1.4784 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4656 -1.6472 -2.2768 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7345 -1.0512 -1.6388 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3821 -1.2333 -0.1537 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4476 -0.5043 0.6089 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6111 0.0081 -0.1207 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0664 -0.6805 -1.3563 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0329 -1.6636 -1.8650 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4086 -1.8583 -3.3321 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7070 -2.5796 -3.2283 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5938 -2.3037 -2.3295 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4682 -1.2628 -1.2991 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5095 -0.2262 -1.5840 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7657 -0.7494 -2.1891 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0086 -2.2014 -2.2013 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8503 -3.1104 -2.3067 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7625 -2.5451 -1.0585 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8102 0.5251 -0.4411 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5294 1.8820 -0.5734 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7785 2.6874 -0.8827 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3065 3.5086 0.2457 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2210 3.9807 1.1733 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2291 2.8720 1.4673 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6734 2.4340 0.3043 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9144 1.7768 2.2207 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0842 0.7525 2.6396 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7609 4.3412 2.4295 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2949 2.8922 1.0043 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4933 3.6157 -1.9241 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7353 -1.8229 0.0964 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4493 -2.6724 0.2464 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6925 -1.6658 -1.2992 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8677 -1.9508 0.0292 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3361 -1.9156 0.3755 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5922 -2.3423 1.7760 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9960 -2.3859 2.2345 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8708 -3.3356 1.4458 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7099 -1.0771 2.3268 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8021 -0.3991 1.1401 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4919 0.7816 1.2824 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6244 0.8606 0.2937 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0865 2.2257 -0.0511 C 0 0 2 0 0 0 0 0 0 0 0 0 8.1751 3.3340 0.3415 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2555 2.9872 1.4670 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5636 1.8242 1.0907 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3277 4.1232 1.7580 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9634 4.4196 0.7917 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2279 2.3109 -1.4581 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2345 0.1620 -0.8455 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5116 -3.3174 0.1775 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5168 0.2326 2.5117 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6895 0.2724 1.0934 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1067 1.0223 0.9996 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5629 -1.6241 1.7343 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7953 0.5058 -0.0212 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7638 0.0660 -1.9742 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5273 -1.3016 -3.3273 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5590 -2.7250 -2.2695 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7341 0.0358 -1.8263 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7821 -1.1211 1.4958 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9150 0.3587 1.1151 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4785 0.0185 0.6091 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4209 1.1061 -0.3237 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1358 0.1071 -2.1706 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2278 -2.6259 -1.3738 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6320 -2.4022 -3.8876 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6210 -0.8553 -3.7398 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8786 -3.3781 -3.9719 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0525 0.4470 -2.3660 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8053 -0.4022 -3.2701 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6740 -0.1957 -1.7603 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7026 -2.4326 -3.0728 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8251 -3.9135 -1.5299 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9350 -3.6980 -3.2686 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6801 -1.8839 -0.3408 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9882 1.9137 -1.5982 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6102 2.0881 -1.2800 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8039 4.4300 -0.1847 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6954 4.8613 0.7922 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4242 3.3322 2.1394 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7316 1.3084 1.6063 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4250 2.1565 3.1346 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8173 0.8748 3.5988 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7474 4.2549 2.4257 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9594 2.4117 0.4641 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3939 3.9455 -2.2195 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7752 -2.0966 0.6148 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3011 -2.7476 0.0412 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3302 -1.0666 0.6402 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0984 -3.4003 -0.4792 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0588 -2.8259 1.1970 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5111 -2.9756 0.4691 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8500 -0.9917 0.0488 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8023 -2.7132 -0.2846 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0629 -1.6191 2.4642 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1131 -3.3625 1.8786 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9807 -2.8131 3.2820 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8627 -3.3263 1.9633 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0529 -2.9633 0.4342 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5164 -4.3837 1.4981 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2415 -0.3834 3.0767 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7605 -1.3125 2.6534 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8161 0.8902 2.3412 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4848 0.3178 0.7667 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1290 2.4300 0.3275 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5499 3.6840 -0.5300 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8310 2.7348 2.3822 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5738 3.8774 2.5398 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8926 4.5655 0.8497 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9664 4.9390 2.2062 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8359 4.3522 0.3087 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9858 1.7834 -1.7882 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1758 0.7181 -1.6478 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7430 -3.8030 -0.6787 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 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 16 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 26 28 1 0 28 29 1 0 25 30 1 0 24 31 1 0 23 32 1 0 15 33 1 1 7 34 1 1 4 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 47 49 1 0 46 50 1 0 45 51 1 0 44 52 1 0 36 53 1 6 36 2 1 0 7 3 1 0 11 6 1 0 15 10 1 0 19 14 1 0 27 22 1 0 48 43 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 1 3 58 1 6 4 59 1 6 5 60 1 0 5 61 1 0 6 62 1 1 8 63 1 0 8 64 1 0 9 65 1 0 9 66 1 0 10 67 1 6 11 68 1 1 12 69 1 0 12 70 1 0 13 71 1 0 16 72 1 6 17 73 1 0 17 74 1 0 18 75 1 6 19 76 1 0 19 77 1 0 20 78 1 0 22 79 1 6 23 80 1 6 24 81 1 6 25 82 1 6 26 83 1 1 28 84 1 0 28 85 1 0 29 86 1 0 30 87 1 0 31 88 1 0 32 89 1 0 33 90 1 0 33 91 1 0 33 92 1 0 34 93 1 0 34 94 1 0 34 95 1 0 37 96 1 0 37 97 1 0 38 98 1 0 38 99 1 0 39100 1 1 40101 1 0 40102 1 0 40103 1 0 41104 1 0 41105 1 0 43106 1 1 44107 1 1 45108 1 1 46109 1 6 47110 1 1 49111 1 0 49112 1 0 49113 1 0 50114 1 0 51115 1 0 52116 1 0 53117 1 0 M END

Standard InCHIKey	VBXHRHABBLLODX-GHJARXIDSA-N
Standard InCHI	InChI=1S/C39H64O14/c1-17(16-49-35-33(46)31(44)29(42)19(3)50-35)8-11-39(48)18(2)28-25(53-39)14-24-22-7-6-20-12-21(41)13-27(38(20,5)23(22)9-10-37(24,28)4)52-36-34(47)32(45)30(43)26(15-40)51-36/h6,17-19,21-36,40-48H,7-16H2,1-5H3/t17-,18+,19-,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]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4([C@@H](C[C@@H](C5)O)O[C@H]6[C@@H]([C@H]([C@H]([C@H](O6)CO)O)O)O)C)C)O[C@]1(CC[C@@H](C)CO[C@H]7[C@H]([C@H]([C@@H]([C@H](O7)C)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	756.43	Volume:	743.631 ? Van der Waals volume.
Dense:	1.017	LogP:	2.678 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.26 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.802 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	36.0
TPSA:	228.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	9.0	Rings:	7.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.145	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.994	Fsp³:	0.949
MCE-18:	135.526 ? 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:	0.647	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? 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:	0.203	Promiscuous compounds:	0.045

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.889	MDCK Permeability:	-5.154
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):	0.638
20% Bioavailability (F20%):	0.991	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.656
Plasma Protein Binding (PPB):	53.386%	Volume Distribution (VD):	-0.427
Fu:	38.423% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.122
BSEP inhibitor:	0.0

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:	0.0
CYP3A4-inhibitor:	0.098	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.006 ? 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):

1.082

Half-life (T1/2):

2.567

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.022
Human Hepatotoxicity (H-HT):	0.672	Drug-induced Liver Injury (DILI):	0.695
AMES Toxicity:	0.946	Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.322	Skin Sensitization:	1.0
Carcinogencity:	0.629	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.106
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.996
Hematotoxicity:	0.831	Drug-induced Nephrotoxicity:	0.972
Genotoxicity:	0.66	RPMI-8226 Immunitoxicity:	0.364
A549 Cytotoxicity:	0.996	Hek293 Cytotoxicity:	0.949
BCF:	1.311 ? 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:	3.348 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.581 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.828 ? 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
NPO4610	Allium atroviolaceum	Species	Amaryllidaceae	Eukaryota	bulbs and flowers	Semirum (2300 m), Isfhan Provinces, Iran	2002-JUN, 2003	PMID[16499315]
NPO4610	Allium atroviolaceum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4610	Allium atroviolaceum	Species	Amaryllidaceae	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
Inhibition	1

Activity Type	# Activity
Tissue	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
NPT548	Tissue	Ileum	Cavia porcellus	Inhibition	=	50	%	PMID[16499315]

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 NPC476539 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	22445
0.1-0.2	23279
0.2-0.3	3413
0.3-0.4	565
0.4-0.5	104
0.5-0.6	23
0.6-0.7	19
0.7-0.8	0
0.8-0.85	0
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	NPC476538
0.869	High Similarity	NPC476540
0.869	High Similarity	NPC476541
0.701	Intermediate Similarity	NPC98696
0.6667	Remote Similarity	NPC73243
0.6667	Remote Similarity	NPC244086
0.6667	Remote Similarity	NPC84956
0.6667	Remote Similarity	NPC102016
0.6667	Remote Similarity	NPC95051
0.663	Remote Similarity	NPC485602
0.6538	Remote Similarity	NPC247037
0.6395	Remote Similarity	NPC473923
0.6355	Remote Similarity	NPC218571
0.6355	Remote Similarity	NPC487615
0.6355	Remote Similarity	NPC249265
0.6344	Remote Similarity	NPC226642
0.6296	Remote Similarity	NPC23808
0.6296	Remote Similarity	NPC87998
0.625	Remote Similarity	NPC473476
0.6211	Remote Similarity	NPC291203
0.6211	Remote Similarity	NPC217205
0.6196	Remote Similarity	NPC485600
0.6162	Remote Similarity	NPC485601
0.596	Remote Similarity	NPC306131
0.596	Remote Similarity	NPC200802
0.5841	Remote Similarity	NPC475357
0.5833	Remote Similarity	NPC148965
0.5728	Remote Similarity	NPC70204
0.5727	Remote Similarity	NPC475487
0.5524	Remote Similarity	NPC485599
0.5455	Remote Similarity	NPC294129
0.5429	Remote Similarity	NPC475670
0.534	Remote Similarity	NPC475431
0.5315	Remote Similarity	NPC98018
0.5315	Remote Similarity	NPC284104
0.5315	Remote Similarity	NPC103616
0.5221	Remote Similarity	NPC470863
0.5185	Remote Similarity	NPC112274
0.5185	Remote Similarity	NPC51154
0.5179	Remote Similarity	NPC475247
0.5138	Remote Similarity	NPC11548
0.5133	Remote Similarity	NPC51520
0.5133	Remote Similarity	NPC303069
0.5104	Remote Similarity	NPC204881
0.5089	Remote Similarity	NPC475182
0.5043	Remote Similarity	NPC470861

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476539 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7475
0.1-0.2	1591
0.2-0.3	75
0.3-0.4	6
0.4-0.5	3
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