NPASS Compound

Natural Product: NPC156242

Natural Product ID	NPC156242
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RFPSRRFCRJPTJM-PURWSFQASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 115121 0 0 0 0 0 0 0 0999 V2000 -4.5094 4.2667 -0.5621 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2765 3.7205 0.6110 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6103 3.1196 0.2267 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6175 1.6200 0.4076 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2431 1.1091 0.0427 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1317 1.7744 0.7780 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6968 0.8627 1.7627 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4078 0.4735 1.6874 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9775 -0.2404 0.4291 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7227 -1.5165 0.1969 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8255 -2.6663 -0.1266 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6723 -2.3080 -1.0310 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0635 -0.9467 -0.6365 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6179 -0.5717 0.5988 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2403 -0.9045 -0.6079 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5247 -0.8535 -0.5922 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2117 -1.8833 -1.3272 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5641 -2.7504 -1.9459 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5641 -1.9345 -1.3639 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2585 -2.9270 -2.0661 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6313 -2.9788 -2.0973 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3539 -2.0204 -1.4140 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6735 -1.0602 -0.7355 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2817 -0.9809 -0.6843 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6682 -0.0604 -0.0313 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3228 0.0451 0.0417 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8265 1.1524 0.8266 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6103 1.7253 0.6905 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1511 2.7518 1.5381 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9278 3.2308 2.5593 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1930 2.6533 2.7176 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6167 1.6594 1.8849 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0047 3.1200 3.7458 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5609 4.2351 3.4404 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7339 -2.1321 -1.4870 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6670 -1.2911 -0.8903 C 0 0 1 0 0 0 0 0 0 0 0 0 10.5121 -2.0494 0.1558 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2377 -0.9949 0.9699 C 0 0 2 0 0 0 0 0 0 0 0 0 12.0339 -0.0707 0.0761 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2396 0.3056 -1.1375 C 0 0 1 0 0 0 0 0 0 0 0 0 12.1028 1.0761 -2.1196 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2720 1.5711 -3.1410 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6031 -0.7470 -1.7645 O 0 0 0 0 0 0 0 0 0 0 0 0 12.2347 1.1035 0.8221 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0327 -1.6410 1.9030 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7055 -2.7884 1.0025 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4908 -3.8734 -2.7408 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0870 -2.2965 -2.3431 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3508 -3.2493 1.0712 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5233 -1.8700 1.2814 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5530 2.8999 1.4435 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9712 1.1084 -1.3036 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6353 1.0867 -0.2915 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5935 0.3921 0.4191 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.9663 0.9285 0.3338 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.7021 0.2502 -0.7998 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.9136 -1.1879 -0.3170 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5863 -1.7213 0.1663 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3212 -2.9574 -0.7207 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1637 -3.6115 -0.3733 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5164 -0.9126 -0.0234 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8505 -1.2259 0.7134 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9837 0.2656 -1.9714 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6430 0.5508 1.5200 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6498 3.7384 0.8932 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7648 3.8073 -1.5333 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6827 5.3815 -0.5900 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4147 4.1750 -0.3028 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5384 4.6179 1.2611 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7283 3.3271 -0.8650 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6888 1.4667 1.5252 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2678 0.0145 0.3359 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2504 1.9593 0.1256 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1896 -0.2053 2.5575 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6988 1.3451 1.7798 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0860 0.4048 -0.4669 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4251 -1.3616 -0.6577 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3952 -3.4822 -0.6183 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0988 -3.0679 -0.8965 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4841 -0.2155 -1.3961 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1056 -3.7660 -2.6542 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2123 -0.3008 -0.1942 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9584 1.4452 -0.1185 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1560 3.1909 1.3940 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5920 1.1921 1.9834 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7220 3.8070 3.5540 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2068 5.1409 3.1238 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2065 -0.4065 -0.3617 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2529 -2.6473 -0.4095 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4569 -0.4165 1.4998 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0164 -0.4966 -0.1380 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4442 1.0237 -0.7980 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5720 1.9516 -1.6292 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8814 0.4686 -2.5893 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8552 1.7559 -3.9278 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9744 0.9882 1.4755 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4167 -0.9075 2.4773 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1867 -2.9802 1.8547 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5708 -4.8553 -2.5560 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6831 -1.5247 -2.8419 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5815 -2.7741 1.4435 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3267 -2.7923 1.5711 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4935 0.4324 -1.8172 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2876 0.3867 1.5073 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0546 2.0234 0.2926 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6823 0.7763 -0.8860 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3252 -1.7256 -1.1938 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6628 -2.1484 1.1972 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3018 -2.6147 -1.7921 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1635 -3.6804 -0.6593 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7391 -3.9115 -1.2370 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6951 -0.8068 0.4163 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1339 1.1171 -2.4761 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0937 0.0164 2.1156 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7146 3.2992 1.7997 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 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 30 34 1 0 22 35 1 0 35 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 40 43 1 0 39 44 1 0 38 45 1 0 37 46 1 0 20 47 1 0 12 48 1 0 11 49 1 0 10 50 1 0 6 51 1 0 5 52 1 0 4 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 58 61 1 0 57 62 1 0 56 63 1 0 55 64 1 0 3 65 1 0 51 2 1 0 61 54 1 0 14 9 1 0 26 16 2 0 32 27 1 0 43 36 1 0 24 19 1 0 1 66 1 0 1 67 1 0 1 68 1 0 2 69 1 1 3 70 1 6 4 71 1 1 5 72 1 1 6 73 1 6 8 74 1 0 8 75 1 0 9 76 1 6 10 77 1 6 11 78 1 6 12 79 1 6 13 80 1 6 21 81 1 0 23 82 1 0 28 83 1 0 29 84 1 0 32 85 1 0 33 86 1 0 34 87 1 0 36 88 1 1 37 89 1 6 38 90 1 1 39 91 1 6 40 92 1 1 41 93 1 0 41 94 1 0 42 95 1 0 44 96 1 0 45 97 1 0 46 98 1 0 47 99 1 0 48100 1 0 49101 1 0 50102 1 0 52103 1 0 54104 1 1 55105 1 6 56106 1 6 57107 1 6 58108 1 1 59109 1 0 59110 1 0 60111 1 0 62112 1 0 63113 1 0 64114 1 0 65115 1 0 M END

Standard InCHIKey	RFPSRRFCRJPTJM-PURWSFQASA-N
Standard InCHI	InChI=1S/C39H50O26/c1-10-21(45)34(64-38-30(54)27(51)23(47)18(8-41)62-38)32(56)36(58-10)57-9-19-24(48)28(52)31(55)39(63-19)65-35-25(49)20-15(44)5-12(59-37-29(53)26(50)22(46)17(7-40)61-37)6-16(20)60-33(35)11-2-3-13(42)14(43)4-11/h2-6,10,17-19,21-24,26-32,34,36-48,50-56H,7-9H2,1H3/t10-,17+,18+,19+,21-,22+,23+,24-,26-,27-,28-,29+,30+,31+,32+,34+,36+,37+,38-,39-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)Oc2c(=O)c3c(cc(cc3oc2c2ccc(c(c2)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)O)O)O)O1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	934.26	Volume:	830.659 ? Van der Waals volume.
Dense:	1.125	LogP:	-1.465 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.165 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.249 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	42.0
TPSA:	427.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	26.0
H-Bond Donor:	16.0	Rings:	7.0
Heavy Atoms:	26.0

MedChem Properties

QED Drug-Likeness Score:	0.075	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.977	Fsp³:	0.615
MCE-18:	185.381 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.642	Fluc inhibitor:	0.296 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.679 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.603 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.316	Promiscuous compounds:	0.603

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.362	MDCK Permeability:	-4.666
Pgp-inhibitor:	0.0	Pgp-substrate:	0.788
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):	0.948
20% Bioavailability (F20%):	0.036	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	64.46%	Volume Distribution (VD):	-0.221
Fu:	30.094% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.031
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:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.396
HLM stability:	0.222 ? 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):

-0.344

Half-life (T1/2):

7.594

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.009
Human Hepatotoxicity (H-HT):	0.607	Drug-induced Liver Injury (DILI):	0.993
AMES Toxicity:	0.979	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.004	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.098	Drug-induced Nephrotoxicity:	0.807
Genotoxicity:	0.225	RPMI-8226 Immunitoxicity:	0.141
A549 Cytotoxicity:	0.884	Hek293 Cytotoxicity:	0.18
BCF:	0.295 ? 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:	2.712 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.519 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.517 ? 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
NPO16116	Aniba canelilla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38005295]
NPO6418	Passalora rosicola	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19510	Origanum floribundum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23040	Methylomonas methanica	Species	Methylococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14708	Macowania corymbosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13937	Leptodontidium elatius	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19165	Comptonia peregrina	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16769	Baccharis hutchisonii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16116	Aniba canelilla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16769	Baccharis hutchisonii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16116	Aniba canelilla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14708	Macowania corymbosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19510	Origanum floribundum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19165	Comptonia peregrina	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23040	Methylomonas methanica	Species	Methylococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6418	Passalora rosicola	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13937	Leptodontidium elatius	Species	n.a.	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 NPC156242 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	24886
0.1-0.2	21048
0.2-0.3	3061
0.3-0.4	400
0.4-0.5	276
0.5-0.6	135
0.6-0.7	33
0.7-0.8	1
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8247	Intermediate Similarity	NPC292019
0.8247	Intermediate Similarity	NPC202908
0.7624	Intermediate Similarity	NPC480441
0.76	Intermediate Similarity	NPC189564
0.7303	Intermediate Similarity	NPC136042
0.7283	Intermediate Similarity	NPC605784
0.7113	Intermediate Similarity	NPC186816
0.7059	Intermediate Similarity	NPC14187
0.6952	Remote Similarity	NPC25523
0.6848	Remote Similarity	NPC84362
0.6837	Remote Similarity	NPC156869
0.6566	Remote Similarity	NPC67105
0.6562	Remote Similarity	NPC116458
0.6562	Remote Similarity	NPC246943
0.6559	Remote Similarity	NPC297987
0.6535	Remote Similarity	NPC488073
0.6509	Remote Similarity	NPC203145
0.65	Remote Similarity	NPC203259
0.65	Remote Similarity	NPC33054
0.65	Remote Similarity	NPC210073
0.65	Remote Similarity	NPC176740
0.65	Remote Similarity	NPC471725
0.65	Remote Similarity	NPC134532
0.65	Remote Similarity	NPC602582
0.6489	Remote Similarity	NPC271692
0.6471	Remote Similarity	NPC470443
0.6381	Remote Similarity	NPC101636
0.6286	Remote Similarity	NPC473073
0.6277	Remote Similarity	NPC289667
0.6238	Remote Similarity	NPC275454
0.6214	Remote Similarity	NPC126784
0.6214	Remote Similarity	NPC241423
0.62	Remote Similarity	NPC251417
0.6095	Remote Similarity	NPC32641
0.6095	Remote Similarity	NPC256188
0.6095	Remote Similarity	NPC35119
0.6078	Remote Similarity	NPC67326
0.6066	Remote Similarity	NPC249560
0.6042	Remote Similarity	NPC277205
0.6042	Remote Similarity	NPC37919
0.6038	Remote Similarity	NPC486577
0.5938	Remote Similarity	NPC249281
0.5922	Remote Similarity	NPC173582
0.5922	Remote Similarity	NPC44931
0.5922	Remote Similarity	NPC265885
0.5922	Remote Similarity	NPC181465
0.5922	Remote Similarity	NPC215710
0.5922	Remote Similarity	NPC473438
0.5922	Remote Similarity	NPC227508
0.5922	Remote Similarity	NPC253788
0.5905	Remote Similarity	NPC64425
0.5888	Remote Similarity	NPC142142
0.5876	Remote Similarity	NPC145038
0.5876	Remote Similarity	NPC56077
0.5876	Remote Similarity	NPC281131
0.5876	Remote Similarity	NPC253662
0.5876	Remote Similarity	NPC179950
0.5876	Remote Similarity	NPC88789
0.5876	Remote Similarity	NPC189142
0.5876	Remote Similarity	NPC77660
0.5876	Remote Similarity	NPC491374
0.5859	Remote Similarity	NPC488071
0.5849	Remote Similarity	NPC65711
0.5842	Remote Similarity	NPC276377
0.5841	Remote Similarity	NPC277532
0.5816	Remote Similarity	NPC46420
0.5794	Remote Similarity	NPC606657
0.5784	Remote Similarity	NPC116864
0.5784	Remote Similarity	NPC244776
0.5769	Remote Similarity	NPC39834
0.5755	Remote Similarity	NPC240306
0.5755	Remote Similarity	NPC488074
0.5727	Remote Similarity	NPC470446
0.5714	Remote Similarity	NPC65563
0.5714	Remote Similarity	NPC470949
0.5714	Remote Similarity	NPC158674
0.5714	Remote Similarity	NPC150164
0.5673	Remote Similarity	NPC480466
0.5645	Remote Similarity	NPC223860
0.5625	Remote Similarity	NPC121703
0.5619	Remote Similarity	NPC471748
0.56	Remote Similarity	NPC42773
0.56	Remote Similarity	NPC45522
0.56	Remote Similarity	NPC599850
0.5586	Remote Similarity	NPC135358
0.5573	Remote Similarity	NPC33083
0.5566	Remote Similarity	NPC22062
0.5566	Remote Similarity	NPC473634
0.5566	Remote Similarity	NPC138811
0.5545	Remote Similarity	NPC476472
0.5545	Remote Similarity	NPC294815
0.5545	Remote Similarity	NPC16194
0.5545	Remote Similarity	NPC611303
0.5524	Remote Similarity	NPC471079
0.5524	Remote Similarity	NPC29958
0.5517	Remote Similarity	NPC470716
0.5514	Remote Similarity	NPC473571
0.5514	Remote Similarity	NPC110941
0.5505	Remote Similarity	NPC483416
0.5505	Remote Similarity	NPC122467
0.5505	Remote Similarity	NPC209296
0.5505	Remote Similarity	NPC473327
0.5455	Remote Similarity	NPC238376
0.5446	Remote Similarity	NPC602448
0.5421	Remote Similarity	NPC479405
0.5421	Remote Similarity	NPC605592
0.5417	Remote Similarity	NPC488078
0.5405	Remote Similarity	NPC471669
0.54	Remote Similarity	NPC323593
0.54	Remote Similarity	NPC203500
0.5372	Remote Similarity	NPC241781
0.537	Remote Similarity	NPC115674
0.537	Remote Similarity	NPC479404
0.5364	Remote Similarity	NPC229409
0.5364	Remote Similarity	NPC72016
0.5357	Remote Similarity	NPC298171
0.5357	Remote Similarity	NPC470445
0.5347	Remote Similarity	NPC27640
0.5304	Remote Similarity	NPC470451
0.53	Remote Similarity	NPC127546
0.53	Remote Similarity	NPC39360
0.53	Remote Similarity	NPC57625
0.53	Remote Similarity	NPC77672
0.53	Remote Similarity	NPC133671
0.53	Remote Similarity	NPC19709
0.53	Remote Similarity	NPC135391
0.53	Remote Similarity	NPC29763
0.53	Remote Similarity	NPC173637
0.53	Remote Similarity	NPC78263
0.53	Remote Similarity	NPC210003
0.53	Remote Similarity	NPC317489
0.53	Remote Similarity	NPC250069
0.53	Remote Similarity	NPC223424
0.53	Remote Similarity	NPC600591
0.5294	Remote Similarity	NPC488086
0.5283	Remote Similarity	NPC8856
0.5278	Remote Similarity	NPC155877
0.5273	Remote Similarity	NPC245452
0.5273	Remote Similarity	NPC479403
0.5268	Remote Similarity	NPC89127
0.5253	Remote Similarity	NPC67037
0.5253	Remote Similarity	NPC255615
0.5214	Remote Similarity	NPC164704
0.5203	Remote Similarity	NPC192539
0.5196	Remote Similarity	NPC24043
0.5189	Remote Similarity	NPC254855
0.5189	Remote Similarity	NPC94610
0.5179	Remote Similarity	NPC488089
0.5149	Remote Similarity	NPC19388
0.5149	Remote Similarity	NPC240431
0.5149	Remote Similarity	NPC55786
0.5146	Remote Similarity	NPC59534
0.5138	Remote Similarity	NPC303913
0.5138	Remote Similarity	NPC3583
0.5135	Remote Similarity	NPC483415
0.5133	Remote Similarity	NPC473071
0.5133	Remote Similarity	NPC483413
0.5124	Remote Similarity	NPC298666
0.5122	Remote Similarity	NPC209550
0.5122	Remote Similarity	NPC138990
0.5098	Remote Similarity	NPC64305
0.5096	Remote Similarity	NPC285197
0.5094	Remote Similarity	NPC190003
0.5093	Remote Similarity	NPC139320
0.5091	Remote Similarity	NPC169733
0.5089	Remote Similarity	NPC37668
0.5088	Remote Similarity	NPC470449
0.5085	Remote Similarity	NPC470715
0.5085	Remote Similarity	NPC303694
0.5049	Remote Similarity	NPC305811
0.5049	Remote Similarity	NPC52550
0.5048	Remote Similarity	NPC601144
0.5047	Remote Similarity	NPC265115
0.5043	Remote Similarity	NPC223426
0.5042	Remote Similarity	NPC311850
0.5041	Remote Similarity	NPC470720

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC156242 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6082
0.1-0.2	3008
0.2-0.3	50
0.3-0.4	4
0.4-0.5	2
0.5-0.6	1
0.6-0.7	2
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
0.7449	Intermediate Similarity	NPD7251	Phase 2
0.65	Remote Similarity	NPD6797	Phase 2
0.6355	Remote Similarity	NPD7808	Phase 3
0.5505	Remote Similarity	NPD7054	Phase 4

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