NPASS Compound

Natural Product: NPC161434

Natural Product ID	NPC161434
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-Beta-D-Xylopyranosyl-3Beta-Hydroxyurs-12,18(19)-Dien-28-Oic Acid 28-Beta-D-Glucopyranosyl Ester
IUPAC Name	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2R,4aS,6aR,6aS,6bR,8aR,10S,12aR)-1,2,6a,6b,9,9,12a-heptamethyl-10-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-3,4,5,6,6a,7,8,8a,10,11,12,13-dodecahydro-2H-picene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2269905
PubChem CID	76312408
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 117123 0 0 0 0 0 0 0 0999 V2000 4.9826 -4.5515 1.4569 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9093 -3.0048 1.1293 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5978 -2.3696 2.2503 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7208 -1.5483 3.1765 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8011 -0.7537 2.3370 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9345 0.2672 3.0051 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9046 0.7797 1.9739 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8117 -0.2094 1.9117 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0164 -0.1521 3.2206 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4341 -1.5905 1.7316 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5908 -2.5897 1.5058 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9040 -2.4025 1.3960 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2988 -1.0007 1.0984 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5434 -0.8304 0.2838 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6892 -1.8127 -0.8019 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7470 -1.1392 1.2180 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0354 -1.0076 0.4382 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2201 0.3568 -0.1511 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0009 0.9741 -0.7491 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9179 0.7772 -2.2500 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1488 2.4959 -0.5446 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7511 0.6094 -0.0358 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5348 1.2518 -0.6354 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4997 1.2931 0.4776 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1244 -0.1509 0.7372 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6777 -0.5802 -0.4481 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2973 0.2695 -1.0436 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3979 0.9791 -0.6368 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8318 1.8964 -1.7433 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7350 2.9412 -1.1288 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4167 2.3374 0.0584 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5829 0.8571 0.0121 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4746 0.1350 -0.3542 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8391 2.7845 1.2697 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6921 3.3111 -2.0938 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7766 2.4107 -2.4541 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8681 -1.8050 1.7200 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4122 -2.7978 1.0886 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6210 -3.6725 0.1908 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5543 -0.0060 1.2981 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6017 1.2773 1.4461 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2032 -0.4603 0.2112 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9011 0.2864 -0.7456 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3532 -0.0399 -0.8722 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0066 1.0350 -1.7188 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2141 1.4208 -2.9242 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7290 1.3621 -2.6949 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9988 1.5132 -4.0095 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4181 2.6758 -4.6536 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3393 0.2100 -2.0164 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5329 2.7661 -3.2211 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3062 0.6761 -2.0714 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0291 -0.0724 0.3483 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0604 -4.8033 1.5117 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4495 -4.6654 2.4156 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5065 -5.0529 0.6165 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3675 -2.9870 0.1347 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1858 -3.0612 2.8873 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3640 -1.6380 1.8575 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3253 -0.9667 3.9010 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1261 -2.2802 3.7771 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5090 1.1652 3.3021 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5100 -0.1809 3.8865 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5723 1.7613 2.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4232 0.8565 1.0215 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3255 -1.1388 3.5391 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7566 0.6521 3.2037 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6719 0.2006 4.0798 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9637 -3.5754 1.5076 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2658 -3.1201 0.6002 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3927 -2.8012 2.3195 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6281 -0.6072 2.1287 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8459 -2.0558 -1.4273 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0093 -2.7987 -0.3382 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5371 -1.5961 -1.4961 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6832 -2.1454 1.6295 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7326 -0.3260 1.9696 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1647 -1.8351 -0.2974 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8524 -1.1631 1.1850 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5883 1.0156 0.6897 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9147 0.4408 -2.5841 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0820 1.7410 -2.8193 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7468 0.1218 -2.6314 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9810 3.0536 -1.4889 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4928 2.8569 0.2756 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1944 2.7585 -0.2386 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8536 1.1060 0.9839 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7238 2.3096 -0.9046 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1709 0.6443 -1.4610 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3999 1.7894 0.0680 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8304 1.8321 1.3608 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7662 -0.7833 -0.2020 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3497 -1.4567 -0.9860 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7802 0.2272 -1.2385 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1584 1.4759 0.3163 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4369 1.2815 -2.4729 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1514 3.8490 -0.9027 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4592 2.7755 0.0808 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9517 0.5383 1.0185 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4136 0.6286 -0.6909 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3855 3.6521 1.0880 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5618 2.8382 -1.9408 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5031 1.7530 -3.1402 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4086 -3.8283 -0.6696 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8595 -3.1985 -0.4280 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5097 -4.7114 0.4840 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8239 1.3645 -0.4426 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4668 -0.9932 -1.4461 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1094 1.9577 -1.0779 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5113 0.8503 -3.8381 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4172 2.2277 -2.0597 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9155 1.6568 -3.7514 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0700 0.6293 -4.6584 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2584 3.4826 -4.1251 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3703 3.0291 -2.7636 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4284 0.8618 -3.0163 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3028 -1.0167 0.5375 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 1 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 18 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 31 34 1 0 30 35 1 0 29 36 1 0 10 37 1 0 37 38 2 0 38 39 1 0 5 40 1 6 40 41 2 0 40 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 48 49 1 0 47 50 1 0 46 51 1 0 45 52 1 0 44 53 1 0 38 2 1 0 50 43 1 0 37 5 1 0 25 8 1 0 33 28 1 0 25 13 1 0 22 14 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 6 3 58 1 0 3 59 1 0 4 60 1 0 4 61 1 0 6 62 1 0 6 63 1 0 7 64 1 0 7 65 1 0 9 66 1 0 9 67 1 0 9 68 1 0 11 69 1 0 12 70 1 0 12 71 1 0 13 72 1 1 15 73 1 0 15 74 1 0 15 75 1 0 16 76 1 0 16 77 1 0 17 78 1 0 17 79 1 0 18 80 1 1 20 81 1 0 20 82 1 0 20 83 1 0 21 84 1 0 21 85 1 0 21 86 1 0 22 87 1 1 23 88 1 0 23 89 1 0 24 90 1 0 24 91 1 0 26 92 1 0 26 93 1 0 26 94 1 0 28 95 1 1 29 96 1 6 30 97 1 1 31 98 1 1 32 99 1 0 32100 1 0 34101 1 0 35102 1 0 36103 1 0 39104 1 0 39105 1 0 39106 1 0 43107 1 1 44108 1 6 45109 1 1 46110 1 6 47111 1 1 48112 1 0 48113 1 0 49114 1 0 51115 1 0 52116 1 0 53117 1 0 M END

Standard InCHIKey	LAJREHMDUQCCEI-NFIAZQJGSA-N
Standard InCHI	InChI=1S/C41H64O12/c1-20-10-15-41(36(49)53-35-33(48)31(46)30(45)24(18-42)51-35)17-16-39(6)22(28(41)21(20)2)8-9-26-38(5)13-12-27(37(3,4)25(38)11-14-40(26,39)7)52-34-32(47)29(44)23(43)19-50-34/h8,20,23-27,29-35,42-48H,9-19H2,1-7H3/t20-,23-,24-,25+,26-,27+,29+,30-,31+,32-,33-,34+,35+,38+,39-,40-,41+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O)C2=C1C)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	748.44	Volume:	755.37 ? Van der Waals volume.
Dense:	0.991	LogP:	2.921 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.346 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.686 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	39.0
TPSA:	195.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.161	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.857	Fsp³:	0.878
MCE-18:	144.545 ? 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:	0.964	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.292 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.176	Promiscuous compounds:	0.11

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.927	MDCK Permeability:	-5.113
Pgp-inhibitor:	0.0	Pgp-substrate:	0.111
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):	0.0
20% Bioavailability (F20%):	0.094	30% Bioavailability (F30%):	0.719
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077	MRP1:	0.053
Plasma Protein Binding (PPB):	75.711%	Volume Distribution (VD):	-0.291
Fu:	15.957% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.444
BSEP inhibitor:	0.014

ADMET: Metabolism

CYP1A2-inhibitor:	0.214	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.101	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.779	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.092
HLM stability:	0.029 ? 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):

0.46

Half-life (T1/2):

2.374

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.005
Human Hepatotoxicity (H-HT):	0.681	Drug-induced Liver Injury (DILI):	0.825
AMES Toxicity:	0.941	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.056	Skin Sensitization:	1.0
Carcinogencity:	0.698	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.023
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.988
Hematotoxicity:	0.697	Drug-induced Nephrotoxicity:	0.995
Genotoxicity:	0.195	RPMI-8226 Immunitoxicity:	0.125
A549 Cytotoxicity:	0.813	Hek293 Cytotoxicity:	0.297
BCF:	1.609 ? 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:	3.803 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.416 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.632 ? 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
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO26261	Streptomyces tendae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27642865]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36235013]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39409699]
NPO9182	Lychnophora passerina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26048	Grateloupia elliptica	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26261	Streptomyces tendae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24698	Protium unifoliolatum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4318	Aspergillus cristatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26283	Streptomyces djakartensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25339	Trillium smallii	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25649	Calliandra haematocephala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26261	Streptomyces tendae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26345	Sideroxylon tomentosum	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25992	Lasallia papulosa	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24698	Protium unifoliolatum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25765	Dryopteris aemula	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26399	Crepidiastrum lanceolatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4318	Aspergillus cristatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26048	Grateloupia elliptica	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26283	Streptomyces djakartensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28950	Angelonia integerrima	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9182	Lychnophora passerina	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
Inhibition	2

Activity Type	# Activity
Cell line	1
Organism	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
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	64.9	%	PMID[31255927]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	33.0	%	PMID[17329884]

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 NPC161434 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	18276
0.1-0.2	26264
0.2-0.3	3918
0.3-0.4	1001
0.4-0.5	317
0.5-0.6	56
0.6-0.7	9
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9012	High Similarity	NPC195132
0.7294	Intermediate Similarity	NPC190837
0.7011	Intermediate Similarity	NPC65590
0.7011	Intermediate Similarity	NPC125923
0.6932	Remote Similarity	NPC212968
0.6889	Remote Similarity	NPC128925
0.6774	Remote Similarity	NPC78046
0.6667	Remote Similarity	NPC204458
0.6667	Remote Similarity	NPC90856
0.6374	Remote Similarity	NPC64106
0.617	Remote Similarity	NPC256798
0.6082	Remote Similarity	NPC1046
0.604	Remote Similarity	NPC469946
0.5979	Remote Similarity	NPC189884
0.5979	Remote Similarity	NPC138334
0.5755	Remote Similarity	NPC297263
0.57	Remote Similarity	NPC48499
0.5636	Remote Similarity	NPC187290
0.5631	Remote Similarity	NPC295371
0.5596	Remote Similarity	NPC301449
0.5596	Remote Similarity	NPC601290
0.5588	Remote Similarity	NPC475516
0.5577	Remote Similarity	NPC263756
0.5577	Remote Similarity	NPC213674
0.5534	Remote Similarity	NPC58448
0.55	Remote Similarity	NPC214484
0.5495	Remote Similarity	NPC31838
0.5495	Remote Similarity	NPC481078
0.5455	Remote Similarity	NPC481079
0.5446	Remote Similarity	NPC11242
0.5437	Remote Similarity	NPC235405
0.5405	Remote Similarity	NPC295823
0.5405	Remote Similarity	NPC174720
0.5405	Remote Similarity	NPC475467
0.5385	Remote Similarity	NPC249848
0.5385	Remote Similarity	NPC107966
0.5377	Remote Similarity	NPC112352
0.537	Remote Similarity	NPC148417
0.537	Remote Similarity	NPC63159
0.5357	Remote Similarity	NPC104137
0.5357	Remote Similarity	NPC26626
0.5339	Remote Similarity	NPC481080
0.5333	Remote Similarity	NPC39211
0.5327	Remote Similarity	NPC160415
0.5283	Remote Similarity	NPC161674
0.5278	Remote Similarity	NPC480475
0.5243	Remote Similarity	NPC179434
0.5229	Remote Similarity	NPC235438
0.5225	Remote Similarity	NPC281148
0.5214	Remote Similarity	NPC123199
0.5196	Remote Similarity	NPC473481
0.5189	Remote Similarity	NPC157868
0.5185	Remote Similarity	NPC30735
0.5185	Remote Similarity	NPC117714
0.5185	Remote Similarity	NPC30289
0.5169	Remote Similarity	NPC283417
0.5169	Remote Similarity	NPC200049
0.5143	Remote Similarity	NPC139894
0.5138	Remote Similarity	NPC164389
0.5138	Remote Similarity	NPC46665
0.5093	Remote Similarity	NPC75417
0.5093	Remote Similarity	NPC223301
0.5093	Remote Similarity	NPC171544
0.5091	Remote Similarity	NPC475591
0.5091	Remote Similarity	NPC236870
0.5091	Remote Similarity	NPC68175
0.5083	Remote Similarity	NPC4749
0.5049	Remote Similarity	NPC269095
0.5043	Remote Similarity	NPC123522

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC161434 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6768
0.1-0.2	2321
0.2-0.3	52
0.3-0.4	9
0.4-0.5	0
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