NPASS Compound

Natural Product: NPC237727

Natural Product ID	NPC237727
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GTUPIAZMULBSIN-IPCMTAOJSA-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 114120 0 0 0 0 0 0 0 0999 V2000 11.5262 0.2072 2.6355 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8238 -0.0181 1.2962 C 0 0 1 0 0 0 0 0 0 0 0 0 11.7724 -0.8554 0.4441 C 0 0 1 0 0 0 0 0 0 0 0 0 10.9937 -1.4305 -0.7427 C 0 0 2 0 0 0 0 0 0 0 0 0 9.6478 -0.7180 -0.8104 C 0 0 2 0 0 0 0 0 0 0 0 0 8.9052 -0.9820 0.4601 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6933 -0.2835 0.4259 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6082 -1.1490 0.4904 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3340 -0.3009 0.5148 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4021 0.6300 1.7254 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6313 0.0012 2.8775 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1809 -0.2220 2.4821 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1054 -0.4225 0.9862 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2177 -1.0881 0.5575 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9396 -1.2046 0.6500 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7198 -0.6326 0.3587 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1636 -0.5370 1.4530 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1183 -0.9486 2.5961 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3890 0.0386 1.2179 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2565 0.1322 2.2961 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4889 0.7042 2.0847 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8993 1.1882 0.8499 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0067 1.0731 -0.1843 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7373 0.4988 -0.0269 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9079 0.3966 -1.0123 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3001 -0.1547 -0.8489 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1753 -0.2263 -2.0279 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2636 -1.0329 -2.1391 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1054 -1.0057 -3.2587 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8204 -0.1324 -4.2846 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7186 0.6762 -4.1644 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8968 0.6584 -3.0838 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6339 -0.0714 -5.4204 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1552 1.7318 0.7902 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7078 2.2555 -0.3632 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9495 1.4480 -0.7834 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5267 2.1103 -1.9833 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9394 3.4083 -2.3853 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4591 4.2568 -1.2458 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5760 5.2251 -0.8916 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6649 4.4488 -0.4615 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1888 3.5440 -0.0988 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8647 3.1850 -3.2430 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9193 2.2424 -1.8689 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6022 0.1286 -1.0413 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2807 -0.6950 -0.1600 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1924 -1.6117 -0.9468 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1804 -2.1747 0.0420 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5315 -2.2736 1.3902 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0435 -2.4049 1.3706 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5936 -3.8049 0.9952 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2728 -4.7502 1.7663 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3982 -1.4216 0.6388 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9193 -1.2282 2.2398 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7898 -3.3414 -0.3571 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8941 -0.8346 -1.8606 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9274 -0.3249 3.5606 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4335 0.9021 2.8741 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2761 -1.1354 3.2945 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9415 1.8927 1.4161 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6523 -0.6601 1.5583 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9118 -1.2076 -1.9003 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7106 -2.7588 -0.4177 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7776 -0.0464 -0.0732 O 0 0 0 0 0 0 0 0 0 0 0 0 12.3982 0.8673 2.5263 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8137 0.6442 3.3642 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7917 -0.7988 3.0582 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6704 0.9557 0.8191 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2354 -1.6700 1.0196 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5947 -1.3038 -1.6425 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8224 0.3652 -0.9189 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6233 -2.0610 0.5581 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6712 -1.8340 1.3491 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5879 -1.6963 -0.4804 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3330 0.3157 -0.3869 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4573 0.6937 2.0363 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6419 0.7437 3.6994 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8095 -1.1048 2.9828 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9828 0.5849 0.4995 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1992 0.7962 2.9037 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2629 1.4283 -1.1638 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5295 -1.7688 -1.4028 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9751 -1.6701 -3.3087 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5164 1.3628 -5.0011 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0273 1.3024 -2.9984 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6340 -0.8926 -6.0153 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0712 2.2617 -1.2632 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6924 1.5258 0.0635 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3819 1.4045 -2.8564 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7181 3.9492 -3.0036 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5815 4.8712 -1.5319 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9449 5.7455 -1.8063 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3302 5.8994 -0.0613 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3998 3.8398 0.2921 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4703 4.0351 -3.5728 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3508 2.2170 -2.7676 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9110 -0.0735 0.4905 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6434 -2.3637 -1.5281 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0018 -1.4092 0.1426 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9253 -3.2135 1.8713 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6958 -2.2556 2.4353 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6695 -4.0045 -0.0867 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5099 -3.9569 1.2546 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9668 -5.2329 1.2511 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6914 -1.4762 3.1737 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9111 -3.3112 -1.3513 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3580 -0.7826 -2.7156 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0222 -1.3380 3.7285 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0973 1.4241 2.1206 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1136 -0.8302 3.7698 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4689 2.1863 0.6102 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5468 -1.2138 -2.6830 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6359 -2.8309 0.5821 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9207 0.7795 0.4275 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 30 33 1 0 22 34 1 0 34 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 39 42 1 0 38 43 1 0 37 44 1 0 36 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 50 53 1 0 49 54 1 0 48 55 1 0 47 56 1 0 20 57 1 0 12 58 1 0 11 59 1 0 10 60 1 0 6 61 1 0 5 62 1 0 4 63 1 0 3 64 1 0 61 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 42 35 1 0 53 46 1 0 24 19 1 0 1 65 1 0 1 66 1 0 1 67 1 0 2 68 1 6 3 69 1 1 4 70 1 6 5 71 1 6 6 72 1 1 8 73 1 0 8 74 1 0 9 75 1 6 10 76 1 1 11 77 1 1 12 78 1 1 13 79 1 6 21 80 1 0 23 81 1 0 28 82 1 0 29 83 1 0 31 84 1 0 32 85 1 0 33 86 1 0 35 87 1 6 36 88 1 1 37 89 1 6 38 90 1 6 39 91 1 6 40 92 1 0 40 93 1 0 41 94 1 0 43 95 1 0 44 96 1 0 46 97 1 1 47 98 1 6 48 99 1 1 49100 1 1 50101 1 1 51102 1 0 51103 1 0 52104 1 0 54105 1 0 55106 1 0 56107 1 0 57108 1 0 58109 1 0 59110 1 0 60111 1 0 62112 1 0 63113 1 0 64114 1 0 M END

Standard InCHIKey	GTUPIAZMULBSIN-IPCMTAOJSA-N
Standard InCHI	InChI=1S/C39H50O25/c1-11-21(44)26(49)30(53)36(57-11)56-10-19-24(47)28(51)32(55)38(62-19)63-34-25(48)20-15(43)6-14(7-16(20)59-33(34)12-2-4-13(42)5-3-12)58-39-35(29(52)23(46)18(9-41)61-39)64-37-31(54)27(50)22(45)17(8-40)60-37/h2-7,11,17-19,21-24,26-32,35-47,49-55H,8-10H2,1H3/t11-,17+,18+,19+,21-,22+,23+,24+,26+,27-,28-,29-,30+,31+,32+,35+,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(cc2)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)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)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	918.26	Volume:	821.869 ? Van der Waals volume.
Dense:	1.117	LogP:	-1.046 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.211 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.585 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	42.0
TPSA:	407.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	25.0
H-Bond Donor:	15.0	Rings:	7.0
Heavy Atoms:	25.0

MedChem Properties

QED Drug-Likeness Score:	0.08	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.89	Fsp³:	0.615
MCE-18:	181.746 ? 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:	0.628	Fluc inhibitor:	0.262 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.647 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.473 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.319	Promiscuous compounds:	0.594

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.325	MDCK Permeability:	-4.621
Pgp-inhibitor:	0.0	Pgp-substrate:	0.968
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):	0.999
20% Bioavailability (F20%):	0.163	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):	69.382%	Volume Distribution (VD):	-0.173
Fu:	27.713% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.042
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:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.579
HLM stability:	0.0 ? 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):

0.074

Half-life (T1/2):

6.06

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.007
Human Hepatotoxicity (H-HT):	0.764	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.975	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.009	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.125	Drug-induced Nephrotoxicity:	0.947
Genotoxicity:	0.711	RPMI-8226 Immunitoxicity:	0.338
A549 Cytotoxicity:	0.818	Hek293 Cytotoxicity:	0.385
BCF:	0.297 ? 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:	2.627 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.398 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.452 ? 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
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1080/10412905.2001.9699624]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11912066]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[12419922]
NPO29391	Papaver bracteatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17226487]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21188975]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[21435874]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30813368]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38695450]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38851735]
NPO29303	Salvia multicaulis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9428161]
NPO29303	Salvia multicaulis	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[9428161]
NPO29303	Salvia multicaulis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29391	Papaver bracteatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29391	Papaver bracteatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29391	Papaver bracteatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29105	Meconopsis punicea	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29105	Meconopsis punicea	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29391	Papaver bracteatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29391	Papaver bracteatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24627	Chondromyces robustus	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29323	Glaucium leiocarpum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29105	Meconopsis punicea	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29212	Tanaecium jaroba	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29303	Salvia multicaulis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28876	Narcissus cyclamineus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29050	Lemnalia nitida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29118	Euonymus alatus	Species	Celastraceae	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 NPC237727 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	22382
0.1-0.2	22876
0.2-0.3	3688
0.3-0.4	420
0.4-0.5	235
0.5-0.6	95
0.6-0.7	83
0.7-0.8	1
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8947	High Similarity	NPC25523
0.8387	Intermediate Similarity	NPC32641
0.8387	Intermediate Similarity	NPC256188
0.8387	Intermediate Similarity	NPC35119
0.8261	Intermediate Similarity	NPC186816
0.8182	Intermediate Similarity	NPC480441
0.7979	Intermediate Similarity	NPC240306
0.7917	Intermediate Similarity	NPC142142
0.75	Intermediate Similarity	NPC602448
0.7312	Intermediate Similarity	NPC116458
0.7312	Intermediate Similarity	NPC246943
0.7245	Intermediate Similarity	NPC64425
0.7113	Intermediate Similarity	NPC173582
0.7113	Intermediate Similarity	NPC265885
0.7113	Intermediate Similarity	NPC181465
0.7113	Intermediate Similarity	NPC215710
0.7113	Intermediate Similarity	NPC473438
0.7113	Intermediate Similarity	NPC253788
0.7087	Intermediate Similarity	NPC14187
0.7	Intermediate Similarity	NPC12013
0.7	Intermediate Similarity	NPC11432
0.7	Intermediate Similarity	NPC477613
0.6957	Remote Similarity	NPC297987
0.6939	Remote Similarity	NPC163242
0.6939	Remote Similarity	NPC272068
0.6869	Remote Similarity	NPC65003
0.6848	Remote Similarity	NPC249281
0.6818	Remote Similarity	NPC298666
0.6792	Remote Similarity	NPC189564
0.6768	Remote Similarity	NPC44931
0.6702	Remote Similarity	NPC46420
0.6701	Remote Similarity	NPC276377
0.67	Remote Similarity	NPC65563
0.67	Remote Similarity	NPC470949
0.6698	Remote Similarity	NPC203145
0.6637	Remote Similarity	NPC209550
0.6634	Remote Similarity	NPC473571
0.6634	Remote Similarity	NPC110941
0.66	Remote Similarity	NPC67105
0.6598	Remote Similarity	NPC605784
0.6571	Remote Similarity	NPC292929
0.6571	Remote Similarity	NPC221342
0.6571	Remote Similarity	NPC476470
0.6535	Remote Similarity	NPC203259
0.6535	Remote Similarity	NPC33054
0.6535	Remote Similarity	NPC176740
0.6535	Remote Similarity	NPC471725
0.6535	Remote Similarity	NPC134532
0.6535	Remote Similarity	NPC150164
0.6535	Remote Similarity	NPC156869
0.6535	Remote Similarity	NPC602582
0.6531	Remote Similarity	NPC170052
0.6531	Remote Similarity	NPC135846
0.6471	Remote Similarity	NPC115674
0.6471	Remote Similarity	NPC470444
0.6455	Remote Similarity	NPC311850
0.6442	Remote Similarity	NPC122467
0.6435	Remote Similarity	NPC192539
0.6373	Remote Similarity	NPC210073
0.6373	Remote Similarity	NPC155877
0.6372	Remote Similarity	NPC198199
0.6364	Remote Similarity	NPC164704
0.6316	Remote Similarity	NPC289667
0.6273	Remote Similarity	NPC292019
0.6273	Remote Similarity	NPC202908
0.6261	Remote Similarity	NPC470720
0.625	Remote Similarity	NPC136042
0.6238	Remote Similarity	NPC473682
0.6238	Remote Similarity	NPC251417
0.6214	Remote Similarity	NPC304741
0.6204	Remote Similarity	NPC135358
0.62	Remote Similarity	NPC476215
0.619	Remote Similarity	NPC470443
0.6176	Remote Similarity	NPC471079
0.6168	Remote Similarity	NPC476472
0.6168	Remote Similarity	NPC294815
0.6168	Remote Similarity	NPC16194
0.6168	Remote Similarity	NPC76831
0.614	Remote Similarity	NPC68592
0.6132	Remote Similarity	NPC72016
0.6132	Remote Similarity	NPC473327
0.6117	Remote Similarity	NPC39834
0.6117	Remote Similarity	NPC275454
0.6117	Remote Similarity	NPC227508
0.6095	Remote Similarity	NPC488073
0.6095	Remote Similarity	NPC126784
0.6095	Remote Similarity	NPC241423
0.6091	Remote Similarity	NPC89052
0.6091	Remote Similarity	NPC121703
0.6078	Remote Similarity	NPC8856
0.6071	Remote Similarity	NPC470715
0.6068	Remote Similarity	NPC120952
0.6058	Remote Similarity	NPC22062
0.6058	Remote Similarity	NPC479405
0.6058	Remote Similarity	NPC473634
0.6058	Remote Similarity	NPC303913
0.6058	Remote Similarity	NPC138811
0.6034	Remote Similarity	NPC470717
0.602	Remote Similarity	NPC271692
0.6019	Remote Similarity	NPC195257
0.6019	Remote Similarity	NPC473073
0.6019	Remote Similarity	NPC220173
0.6018	Remote Similarity	NPC277532
0.6017	Remote Similarity	NPC175429
0.6	Remote Similarity	NPC479404
0.5981	Remote Similarity	NPC209296
0.598	Remote Similarity	NPC254855
0.598	Remote Similarity	NPC94610
0.5962	Remote Similarity	NPC470405
0.5948	Remote Similarity	NPC480445
0.5946	Remote Similarity	NPC11468
0.5932	Remote Similarity	NPC138990
0.5929	Remote Similarity	NPC303694
0.5872	Remote Similarity	NPC473071
0.5872	Remote Similarity	NPC89127
0.5859	Remote Similarity	NPC84362
0.5841	Remote Similarity	NPC219043
0.5816	Remote Similarity	NPC77672
0.5816	Remote Similarity	NPC133671
0.5816	Remote Similarity	NPC135391
0.5816	Remote Similarity	NPC78263
0.5816	Remote Similarity	NPC250069
0.5772	Remote Similarity	NPC473554
0.5758	Remote Similarity	NPC323593
0.5758	Remote Similarity	NPC203500
0.5743	Remote Similarity	NPC611303
0.5741	Remote Similarity	NPC479403
0.5727	Remote Similarity	NPC470447
0.5726	Remote Similarity	NPC488739
0.5714	Remote Similarity	NPC111929
0.5714	Remote Similarity	NPC320283
0.5714	Remote Similarity	NPC41121
0.5714	Remote Similarity	NPC139320
0.5702	Remote Similarity	NPC262222
0.5701	Remote Similarity	NPC255157
0.5701	Remote Similarity	NPC259896
0.569	Remote Similarity	NPC488083
0.5676	Remote Similarity	NPC101636
0.5673	Remote Similarity	NPC95866
0.566	Remote Similarity	NPC67326
0.5657	Remote Similarity	NPC108831
0.5657	Remote Similarity	NPC182634
0.5656	Remote Similarity	NPC25946
0.5652	Remote Similarity	NPC473644
0.56	Remote Similarity	NPC158674
0.5593	Remote Similarity	NPC488734
0.5593	Remote Similarity	NPC295625
0.5593	Remote Similarity	NPC488735
0.5593	Remote Similarity	NPC488732
0.5593	Remote Similarity	NPC488738
0.5583	Remote Similarity	NPC480444
0.5565	Remote Similarity	NPC48984
0.5565	Remote Similarity	NPC173837
0.5556	Remote Similarity	NPC122809
0.5556	Remote Similarity	NPC255799
0.5545	Remote Similarity	NPC24043
0.5536	Remote Similarity	NPC287889
0.5536	Remote Similarity	NPC470449
0.5534	Remote Similarity	NPC224530
0.55	Remote Similarity	NPC39360
0.55	Remote Similarity	NPC29763
0.55	Remote Similarity	NPC210003
0.5492	Remote Similarity	NPC480443
0.5478	Remote Similarity	NPC473072
0.5446	Remote Similarity	NPC64305
0.5446	Remote Similarity	NPC475382
0.5446	Remote Similarity	NPC277205
0.5446	Remote Similarity	NPC37919
0.5424	Remote Similarity	NPC470716
0.5421	Remote Similarity	NPC187379
0.541	Remote Similarity	NPC488737
0.54	Remote Similarity	NPC331652
0.5392	Remote Similarity	NPC488080
0.5392	Remote Similarity	NPC169977
0.5377	Remote Similarity	NPC116864
0.5377	Remote Similarity	NPC244776
0.5372	Remote Similarity	NPC162394
0.5372	Remote Similarity	NPC470719
0.5372	Remote Similarity	NPC488740
0.5364	Remote Similarity	NPC488074
0.5357	Remote Similarity	NPC486577
0.5347	Remote Similarity	NPC238376
0.534	Remote Similarity	NPC472459
0.5321	Remote Similarity	NPC605592
0.5315	Remote Similarity	NPC65711
0.5312	Remote Similarity	NPC223860
0.5304	Remote Similarity	NPC244875
0.5294	Remote Similarity	NPC145038
0.5294	Remote Similarity	NPC56077
0.5294	Remote Similarity	NPC281131
0.5294	Remote Similarity	NPC253662
0.5294	Remote Similarity	NPC179950
0.5294	Remote Similarity	NPC88789
0.5294	Remote Similarity	NPC491374
0.5273	Remote Similarity	NPC129264
0.5268	Remote Similarity	NPC606657
0.5263	Remote Similarity	NPC298171
0.5263	Remote Similarity	NPC470445
0.5254	Remote Similarity	NPC470712
0.5246	Remote Similarity	NPC488736

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC237727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5916
0.1-0.2	3168
0.2-0.3	56
0.3-0.4	3
0.4-0.5	3
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
0.7129	Intermediate Similarity	NPD7251	Phase 2
0.6698	Remote Similarity	NPD7808	Phase 3
0.6535	Remote Similarity	NPD6797	Phase 2
0.5981	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