NPASS Compound

Natural Product: NPC188996

Natural Product ID	NPC188996
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FZEHHXRFTMAICH-DCZAGIEQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101672280
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 117124 0 0 0 0 0 0 0 0999 V2000 -10.3840 2.4143 1.9522 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9131 1.9886 1.8478 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8963 0.4737 1.9848 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5678 -0.1074 1.5641 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0068 0.5505 0.3468 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4892 -0.4340 -0.6848 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6324 -0.6240 -1.6908 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3410 0.2983 -1.2796 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3356 1.6540 -0.5587 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9019 2.0869 -0.4703 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1405 1.0360 -1.1812 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7672 0.7599 -0.6745 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9698 2.0382 -0.8219 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4031 1.7816 -1.4059 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9541 0.5417 -0.6885 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4308 0.5240 -0.6970 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0948 -0.4778 -1.5695 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2224 -0.7459 -2.7616 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8618 -1.2626 -2.4332 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2488 -0.6552 -1.2044 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1723 -1.6637 -0.0559 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1728 -0.2954 -1.5507 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0138 -1.5300 -1.6738 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4619 -1.2664 -1.8642 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9828 -0.2219 -0.9178 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8265 -0.5821 0.5196 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4827 -1.5561 -0.8617 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8242 -1.8692 -0.8125 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3445 -1.7678 0.5948 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3357 -2.9238 0.7423 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4603 -4.1560 0.8674 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7158 -4.2039 -0.4754 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2500 -4.3200 -0.1691 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5689 -4.4617 -1.3898 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9621 -3.1482 -1.2743 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5777 -3.9892 1.9082 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2200 -2.7585 1.7597 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0541 -0.6209 0.7896 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6487 0.2384 1.7516 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5696 0.5103 2.8815 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8617 1.1652 2.3636 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5595 1.9543 1.1041 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1518 2.4457 1.2118 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9105 3.3835 0.0392 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0368 2.7271 -1.1752 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2343 1.4194 1.1792 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4742 2.9991 0.9515 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8265 0.1986 2.1804 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0094 1.4201 3.7714 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7927 3.2844 -1.2146 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8795 1.3061 0.6791 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9362 1.3878 -0.2666 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3051 2.4448 0.5622 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9753 1.6058 1.4804 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6244 2.4208 3.0414 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5369 3.4006 1.4855 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3246 2.3813 2.6915 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0676 0.2579 3.0591 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6926 0.0020 1.3656 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6929 -1.1940 1.3549 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8408 0.0043 2.3932 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2763 -1.4217 -0.2812 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5049 -1.5839 -2.2175 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7159 0.2449 -2.3612 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5577 -0.7001 -1.0799 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3889 0.4238 -2.3753 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9771 2.3601 -1.0945 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5525 2.2692 0.5522 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0806 1.1726 -2.2779 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7115 0.4519 0.3799 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7873 2.5049 0.1894 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5086 2.8119 -1.4056 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0768 2.6341 -1.1626 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2923 1.6133 -2.4760 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6217 0.6829 0.3847 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8455 0.3738 0.3444 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7789 1.5637 -0.9733 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0260 -0.0025 -2.0014 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6917 -1.4281 -3.4992 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0964 0.2258 -3.2899 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2274 -1.0951 -3.3500 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8482 -2.3831 -2.3010 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6226 -1.3520 0.6536 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1230 -1.6222 0.5523 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0611 -2.6802 -0.4461 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1251 0.1525 -2.5882 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8894 -2.2482 -0.8485 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6495 -2.0677 -2.5991 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0258 -2.2110 -1.6405 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7141 -0.9434 -2.8971 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6004 0.3158 1.1398 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0188 -1.3533 0.6049 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7219 -1.0466 0.9806 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4430 -1.1412 -1.4031 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4734 -1.8952 1.2521 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8889 -3.0259 -0.2136 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0936 -5.0380 0.9280 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9907 -5.1804 -0.9643 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0306 -5.2085 0.4738 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8883 -3.4045 0.3217 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1917 -4.7665 -2.0931 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0759 -3.7523 2.7179 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1436 -3.1032 1.5725 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7205 -0.2232 2.2129 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9015 -0.3488 3.4567 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2109 1.8401 3.1644 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7141 1.2628 0.2505 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0983 3.0675 2.1459 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6966 4.1757 0.0696 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8986 3.8157 0.0796 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9674 2.7309 -1.5187 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5771 3.5322 1.7993 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1794 0.1643 1.2503 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6890 1.8008 4.3503 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5666 3.4110 -1.8046 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0880 3.0160 -0.0176 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4733 3.1459 0.7524 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 17 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 29 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 43 46 1 0 42 47 1 0 41 48 1 0 40 49 1 0 10 50 1 0 9 51 1 0 5 52 1 6 52 53 1 0 53 2 1 0 51 5 1 0 25 8 1 0 35 28 1 0 46 39 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 1 3 58 1 0 3 59 1 0 4 60 1 0 4 61 1 0 6 62 1 1 7 63 1 0 7 64 1 0 7 65 1 0 8 66 1 6 9 67 1 6 10 68 1 1 11 69 1 6 12 70 1 1 13 71 1 0 13 72 1 0 14 73 1 0 14 74 1 0 15 75 1 1 16 76 1 0 16 77 1 0 17 78 1 6 18 79 1 0 18 80 1 0 19 81 1 0 19 82 1 0 21 83 1 0 21 84 1 0 21 85 1 0 22 86 1 6 23 87 1 0 23 88 1 0 24 89 1 0 24 90 1 0 26 91 1 0 26 92 1 0 26 93 1 0 28 94 1 6 29 95 1 1 30 96 1 6 31 97 1 1 32 98 1 6 33 99 1 0 33100 1 0 34101 1 0 36102 1 0 37103 1 0 39104 1 1 40105 1 1 41106 1 1 42107 1 6 43108 1 1 44109 1 0 44110 1 0 45111 1 0 47112 1 0 48113 1 0 49114 1 0 50115 1 0 53116 1 0 53117 1 0 M END

Standard InCHIKey	FZEHHXRFTMAICH-DCZAGIEQSA-N
Standard InCHI	InChI=1S/C39H64O14/c1-17-7-12-39(48-16-17)18(2)25-33(53-39)29(44)26-21-6-5-19-13-20(8-10-37(19,3)22(21)9-11-38(25,26)4)49-36-34(31(46)28(43)24(15-41)51-36)52-35-32(47)30(45)27(42)23(14-40)50-35/h17-36,40-47H,5-16H2,1-4H3/t17-,18-,19+,20-,21+,22-,23+,24+,25-,26+,27+,28-,29+,30-,31-,32+,33+,34+,35-,36+,37-,38+,39+/m0/s1
SMILES	C[C@H]1CC[C@@]2([C@@H](C)[C@H]3[C@H]([C@@H]([C@H]4[C@@H]5CC[C@@H]6C[C@H](CC[C@]6(C)[C@H]5CC[C@]34C)O[C@H]3[C@@H]([C@H]([C@H]([C@@H](CO)O3)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O)O2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	756.43	Volume:	737.711 ? Van der Waals volume.
Dense:	1.025	LogP:	2.008 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.854 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.648 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	42.0
TPSA:	217.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	8.0	Rings:	8.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.173	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.352	Fsp³:	1.0
MCE-18:	203.846 ? 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:	0.736	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? 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:	0.228	Promiscuous compounds:	0.038

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.036	MDCK Permeability:	-5.071
Pgp-inhibitor:	0.0	Pgp-substrate:	0.125
PAMPA:	0.996 ? 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):	0.012
20% Bioavailability (F20%):	0.711	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018	MRP1:	0.168
Plasma Protein Binding (PPB):	60.15%	Volume Distribution (VD):	-0.393
Fu:	33.312% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.052
BSEP inhibitor:	0.015

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.008	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.006	CYP3A4-substrate:	0.99
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.042
HLM stability:	0.004 ? 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):

0.905

Half-life (T1/2):

2.615

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.057
Human Hepatotoxicity (H-HT):	0.72	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.938	Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.012	Skin Sensitization:	1.0
Carcinogencity:	0.323	Eye Corrosion:	0.0
Eye Irritation:	0.01	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.991
Hematotoxicity:	0.529	Drug-induced Nephrotoxicity:	0.847
Genotoxicity:	0.01	RPMI-8226 Immunitoxicity:	0.254
A549 Cytotoxicity:	0.95	Hek293 Cytotoxicity:	0.863
BCF:	1.538 ? 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:	4.42 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.835 ? 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
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19757853]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21370894]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[8482946]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	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

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

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 NPC188996 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	28218
0.1-0.2	18484
0.2-0.3	2515
0.3-0.4	456
0.4-0.5	115
0.5-0.6	36
0.6-0.7	21
0.7-0.8	0
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8095	Intermediate Similarity	NPC297348
0.8095	Intermediate Similarity	NPC249204
0.8095	Intermediate Similarity	NPC48339
0.8095	Intermediate Similarity	NPC141769
0.8095	Intermediate Similarity	NPC477547
0.7701	Intermediate Similarity	NPC477451
0.7283	Intermediate Similarity	NPC107962
0.7253	Intermediate Similarity	NPC211354
0.6863	Remote Similarity	NPC13193
0.6848	Remote Similarity	NPC474399
0.6774	Remote Similarity	NPC206003
0.6774	Remote Similarity	NPC473610
0.6667	Remote Similarity	NPC6295
0.663	Remote Similarity	NPC294686
0.6531	Remote Similarity	NPC160426
0.6452	Remote Similarity	NPC234352
0.6436	Remote Similarity	NPC92890
0.6354	Remote Similarity	NPC19400
0.6344	Remote Similarity	NPC325828
0.6316	Remote Similarity	NPC222731
0.63	Remote Similarity	NPC475351
0.6154	Remote Similarity	NPC128572
0.6105	Remote Similarity	NPC291203
0.6105	Remote Similarity	NPC217205
0.6075	Remote Similarity	NPC475625
0.604	Remote Similarity	NPC113044
0.604	Remote Similarity	NPC283829
0.604	Remote Similarity	NPC161676
0.602	Remote Similarity	NPC107188
0.5943	Remote Similarity	NPC184617
0.5865	Remote Similarity	NPC475643
0.5842	Remote Similarity	NPC125324
0.5794	Remote Similarity	NPC97700
0.5794	Remote Similarity	NPC30856
0.5784	Remote Similarity	NPC141433
0.5758	Remote Similarity	NPC128123
0.57	Remote Similarity	NPC54619
0.567	Remote Similarity	NPC177834
0.566	Remote Similarity	NPC477809
0.5625	Remote Similarity	NPC485594
0.5607	Remote Similarity	NPC471464
0.5596	Remote Similarity	NPC475319
0.5575	Remote Similarity	NPC132080
0.5534	Remote Similarity	NPC485595
0.55	Remote Similarity	NPC250393
0.5481	Remote Similarity	NPC195297
0.5463	Remote Similarity	NPC51172
0.5463	Remote Similarity	NPC49032
0.54	Remote Similarity	NPC210157
0.531	Remote Similarity	NPC232037
0.5273	Remote Similarity	NPC480555
0.5273	Remote Similarity	NPC150372
0.5263	Remote Similarity	NPC470864
0.5258	Remote Similarity	NPC24960
0.5253	Remote Similarity	NPC181845
0.5221	Remote Similarity	NPC116756
0.5196	Remote Similarity	NPC292467
0.5185	Remote Similarity	NPC473601
0.5182	Remote Similarity	NPC300557
0.5172	Remote Similarity	NPC233433
0.5143	Remote Similarity	NPC485601
0.5046	Remote Similarity	NPC40440
0.5045	Remote Similarity	NPC274200
0.5043	Remote Similarity	NPC480553
0.5042	Remote Similarity	NPC470866

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC188996 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7792
0.1-0.2	1279
0.2-0.3	68
0.3-0.4	6
0.4-0.5	3
0.5-0.6	1
0.6-0.7	1
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
0.6344	Remote Similarity	NPD8171	Phase 2
0.5385	Remote Similarity	NPD8170	Phase 2

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