NPASS Compound

Natural Product: NPC121453

Natural Product ID	NPC121453
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Atroviolaceoside
IUPAC Name	n.a.
Synonyms	Atroviolaceoside
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL449185
PubChem CID	11614761
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 119126 0 0 0 0 0 0 0 0999 V2000 8.1529 -1.6011 -1.2177 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4471 -0.4056 -0.6738 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5844 -0.8620 0.5096 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7186 0.3804 1.4001 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4906 1.1679 0.9051 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5023 0.0739 1.0063 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1426 0.2770 0.4564 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4936 1.5338 0.9921 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1777 1.6587 0.2076 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3437 0.5119 0.6670 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0474 0.6340 0.1731 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9435 -0.5060 0.5180 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3298 -1.6725 1.1641 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1295 -1.8027 1.2200 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9330 -0.8380 0.3678 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8338 -1.2223 -1.0730 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3515 -0.9353 0.8737 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0081 -2.2320 0.5401 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4829 -2.2754 0.6304 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1520 -1.0100 0.1533 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8666 -0.8606 -1.3119 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8255 -1.8450 2.4850 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6834 -0.8829 -0.6188 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0278 -0.6377 -0.5216 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4277 0.2434 -1.6833 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9180 0.2962 -1.7770 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5736 -0.3028 -0.5242 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0560 -1.6813 -0.2544 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8424 -2.7450 -1.0013 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1794 -2.7099 -0.6946 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7307 -1.8358 -0.6628 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9479 -0.3734 -0.7231 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6458 0.3905 0.2102 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4898 1.3739 -0.5743 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.9751 1.0776 -0.3912 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.3083 1.0214 1.0996 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1683 0.3844 1.8645 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.6825 -0.5030 2.9801 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3751 0.2728 3.9117 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4787 -0.4400 0.9525 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.4333 2.3626 1.4951 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3655 -0.0743 -1.0565 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2290 2.6468 -0.1284 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4338 -0.4065 -2.8640 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8302 1.4995 -1.6092 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5234 1.5842 -1.1375 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9037 0.9621 1.1587 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3863 0.6184 -0.0773 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4150 1.9160 -0.8977 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7616 2.6212 -0.6784 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8096 1.7997 -1.3974 C 0 0 1 0 0 0 0 0 0 0 0 0 12.1361 2.0307 -0.7058 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1050 1.2903 -1.3466 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3704 0.3460 -1.2551 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6900 0.1440 -0.0735 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1645 -1.6426 -2.3324 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1645 -1.7487 -0.7852 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5890 -2.5335 -0.9171 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8815 0.1003 -1.4513 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0381 -1.7554 0.9966 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5096 0.1271 2.4539 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2998 2.0522 1.5104 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6230 1.4079 -0.1895 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4032 -0.2795 2.0533 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0849 0.3353 -0.6436 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1144 2.4203 0.8715 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1800 1.3979 2.0558 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6512 2.5908 0.4633 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3085 0.5770 1.7917 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4332 1.6254 0.5646 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0201 0.8107 -0.9308 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7285 -0.0866 1.2186 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7177 -2.6050 0.6463 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5055 -2.8271 0.9683 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5097 -1.6313 2.2720 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1108 -0.8937 -1.5519 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6379 -0.8013 -1.7105 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8169 -2.3388 -1.1604 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2687 -0.8809 2.0002 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6978 -2.6229 -0.4621 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6016 -2.9967 1.2684 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8339 -2.5803 1.6489 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8649 -3.0929 -0.0498 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9281 -1.4083 -1.5508 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6582 -1.4656 -1.8481 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8369 0.1665 -1.6707 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2605 -2.5529 2.9006 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2274 -0.1692 0.4701 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0683 -0.3006 -2.6029 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2419 1.3579 -1.8591 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3161 0.3476 0.3561 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1348 -1.8757 0.8227 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3598 -3.7163 -0.7451 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6331 -2.5971 -2.0877 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6047 -3.5265 -1.0443 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9878 0.9018 0.9166 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3000 1.3212 -1.6565 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5146 1.9275 -0.8573 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2351 0.4533 1.2663 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4543 1.1121 2.2793 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3293 -1.2835 2.5253 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8040 -0.9823 3.4572 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0142 1.1958 3.8614 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3433 2.4438 1.9108 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9952 -0.6230 -0.5238 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0146 3.2310 -0.8794 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3009 -0.0857 -3.1577 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7146 1.8169 -2.5603 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4007 2.4822 -1.5817 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1987 1.7474 -1.9539 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6573 2.6373 -0.5090 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9716 2.5370 0.4103 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6709 3.6443 -1.0430 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8091 2.1112 -2.4596 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9874 1.7642 0.3576 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4096 3.0973 -0.7278 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5271 1.8692 -2.0415 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8036 0.1075 -2.1630 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2928 -0.2719 -1.2101 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 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 13 22 1 0 12 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 27 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 38 39 1 0 37 40 1 0 36 41 1 0 35 42 1 0 34 43 1 0 26 44 1 0 25 45 1 0 9 46 1 0 4 47 1 0 48 47 1 1 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 51 54 1 0 54 55 1 0 48 2 1 0 20 3 1 0 31 24 1 0 40 33 1 0 55 48 1 0 20 6 1 0 17 7 1 0 15 10 1 0 1 56 1 0 1 57 1 0 1 58 1 0 2 59 1 6 3 60 1 1 4 61 1 1 5 62 1 0 5 63 1 0 6 64 1 1 7 65 1 6 8 66 1 0 8 67 1 0 9 68 1 6 10 69 1 1 11 70 1 0 11 71 1 0 12 72 1 1 13 73 1 6 14 74 1 0 14 75 1 0 16 76 1 0 16 77 1 0 16 78 1 0 17 79 1 1 18 80 1 0 18 81 1 0 19 82 1 0 19 83 1 0 21 84 1 0 21 85 1 0 21 86 1 0 22 87 1 0 24 88 1 1 25 89 1 6 26 90 1 6 27 91 1 1 28 92 1 1 29 93 1 0 29 94 1 0 30 95 1 0 33 96 1 1 34 97 1 6 35 98 1 6 36 99 1 6 37100 1 1 38101 1 0 38102 1 0 39103 1 0 41104 1 0 42105 1 0 43106 1 0 44107 1 0 45108 1 0 46109 1 0 49110 1 0 49111 1 0 50112 1 0 50113 1 0 51114 1 6 52115 1 0 52116 1 0 53117 1 0 54118 1 0 54119 1 0 M END

Standard InCHIKey	UPXMNFSCVVTVFO-IZISHBDUSA-N
Standard InCHI	InChI=1S/C39H64O16/c1-16-28-25(55-39(16)7-4-17(12-40)15-50-39)9-20-18-8-22(43)21-10-24(23(44)11-38(21,3)19(18)5-6-37(20,28)2)51-35-33(49)31(47)34(27(14-42)53-35)54-36-32(48)30(46)29(45)26(13-41)52-36/h16-36,40-49H,4-15H2,1-3H3/t16-,17-,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]1[C@H]2[C@H](C[C@H]3[C@@H]4C[C@H]([C@H]5C[C@H]([C@@H](C[C@]5(C)[C@H]4CC[C@]23C)O)O[C@H]2[C@@H]([C@H]([C@H]([C@@H](CO)O2)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)O)O)O[C@@]21CC[C@@H](CO)CO2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	788.42	Volume:	755.292 ? Van der Waals volume.
Dense:	1.044	LogP:	0.229 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.035 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.358 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	42.0
TPSA:	257.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	10.0	Rings:	8.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.13	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.523	Fsp³:	1.0
MCE-18:	207.692 ? 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:	0.601	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.036 ? 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:	0.242	Promiscuous compounds:	0.014

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.531	MDCK Permeability:	-5.063
Pgp-inhibitor:	0.0	Pgp-substrate:	0.791
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):	0.521
20% Bioavailability (F20%):	0.763	30% Bioavailability (F30%):	0.982
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.091
Plasma Protein Binding (PPB):	35.646%	Volume Distribution (VD):	-0.481
Fu:	54.649% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.036
BSEP inhibitor:	0.002

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:	0.004
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.004
HLM stability:	0.001 ? 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):

0.421

Half-life (T1/2):

2.761

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.014
Human Hepatotoxicity (H-HT):	0.843	Drug-induced Liver Injury (DILI):	0.886
AMES Toxicity:	0.986	Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.01	Skin Sensitization:	1.0
Carcinogencity:	0.389	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.999
Hematotoxicity:	0.496	Drug-induced Nephrotoxicity:	0.957
Genotoxicity:	0.01	RPMI-8226 Immunitoxicity:	0.335
A549 Cytotoxicity:	0.962	Hek293 Cytotoxicity:	0.845
BCF:	0.982 ? 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:	3.245 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.493 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.631 ? 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]
NPO6165	Prunus salicina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28202328]
NPO4610	Allium atroviolaceum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6165	Prunus salicina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6165	Prunus salicina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6165	Prunus salicina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6165	Prunus salicina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8088	Tanacetum densum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8221	Cladonia crispata	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	=	0.0	%	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 NPC121453 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	27381
0.1-0.2	19578
0.2-0.3	2485
0.3-0.4	252
0.4-0.5	98
0.5-0.6	52
0.6-0.7	6
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	Natural Product ID
0.7551	Intermediate Similarity	NPC473518
0.6703	Remote Similarity	NPC325828
0.6505	Remote Similarity	NPC115165
0.6263	Remote Similarity	NPC195297
0.6204	Remote Similarity	NPC83137
0.6105	Remote Similarity	NPC294686
0.6061	Remote Similarity	NPC107962
0.5872	Remote Similarity	NPC232611
0.5859	Remote Similarity	NPC107188
0.5842	Remote Similarity	NPC485595
0.5833	Remote Similarity	NPC475550
0.5816	Remote Similarity	NPC250393
0.5816	Remote Similarity	NPC222731
0.5769	Remote Similarity	NPC473601
0.5766	Remote Similarity	NPC470862
0.5761	Remote Similarity	NPC277715
0.5664	Remote Similarity	NPC31896
0.5648	Remote Similarity	NPC97700
0.5648	Remote Similarity	NPC184617
0.5648	Remote Similarity	NPC30856
0.5625	Remote Similarity	NPC476112
0.5625	Remote Similarity	NPC307534
0.5607	Remote Similarity	NPC6806
0.5579	Remote Similarity	NPC24960
0.5545	Remote Similarity	NPC54619
0.5534	Remote Similarity	NPC470432
0.5534	Remote Similarity	NPC230507
0.5534	Remote Similarity	NPC6295
0.5514	Remote Similarity	NPC477809
0.5464	Remote Similarity	NPC485594
0.5446	Remote Similarity	NPC206003
0.5446	Remote Similarity	NPC473610
0.5431	Remote Similarity	NPC470867
0.5354	Remote Similarity	NPC297348
0.5354	Remote Similarity	NPC249204
0.5354	Remote Similarity	NPC48339
0.5354	Remote Similarity	NPC141769
0.5354	Remote Similarity	NPC477547
0.5333	Remote Similarity	NPC210569
0.5304	Remote Similarity	NPC132080
0.53	Remote Similarity	NPC234352
0.5273	Remote Similarity	NPC151134
0.5253	Remote Similarity	NPC181845
0.5243	Remote Similarity	NPC19400
0.5229	Remote Similarity	NPC248746
0.5172	Remote Similarity	NPC477811
0.514	Remote Similarity	NPC160426
0.5098	Remote Similarity	NPC477451
0.5096	Remote Similarity	NPC211354
0.5093	Remote Similarity	NPC475351
0.5091	Remote Similarity	NPC92890
0.5088	Remote Similarity	NPC32361
0.5088	Remote Similarity	NPC475625
0.5088	Remote Similarity	NPC116756
0.5081	Remote Similarity	NPC244431
0.5057	Remote Similarity	NPC273290
0.5057	Remote Similarity	NPC232044
0.5043	Remote Similarity	NPC232037
0.5039	Remote Similarity	NPC481190

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC121453 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7681
0.1-0.2	1391
0.2-0.3	71
0.3-0.4	4
0.4-0.5	1
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
0.6703	Remote Similarity	NPD8171	Phase 2
0.5842	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