NPASS Compound

Natural Product: NPC473554

Natural Product ID	NPC473554
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	4',5-Dihydroxy-7-Methoxyflavonol 3-O-[6-O-(E)-3,5-Dimethoxy-4-Hydroxycinnamoyl-Beta-D-Glucopyranosyl]-(1->2)-O-[Alpha-L-Rhamnopyranosyl-(1->6)]-Beta-D-Glucopyranoside
IUPAC Name	[(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-4,5-dihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL445480
PubChem CID	44576160
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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 118124 0 0 0 0 0 0 0 0999 V2000 -6.4026 -3.4945 -1.0719 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8665 -4.0025 0.2567 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9646 -5.0908 0.7328 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7031 -4.5505 1.2907 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0458 -3.3689 2.2169 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8481 -2.3384 1.4745 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0835 -2.9763 1.1706 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1304 -1.2560 2.2351 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8277 -0.0086 1.6946 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3852 0.1643 1.4940 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6692 0.3676 2.8462 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1819 0.4451 2.6297 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7612 0.5819 1.1857 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7751 0.9377 0.2259 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0077 1.3590 0.8228 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4819 1.7998 -0.8290 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3685 2.1913 -1.8200 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8683 3.4404 -1.8434 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7387 3.7013 -2.8424 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1145 2.8639 -3.7555 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9947 3.1837 -4.7580 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3949 2.3214 -5.7475 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8871 1.0250 -5.7513 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0110 0.6810 -4.7545 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6121 1.5498 -3.7635 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7198 1.2074 -2.7769 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2348 0.0776 -2.7256 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4908 -0.6334 -4.7494 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2876 2.6872 -6.7603 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5616 4.5402 -0.9410 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2336 5.7611 -1.0578 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9435 6.8920 -0.3358 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8953 6.8419 0.5935 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2119 5.6419 0.7280 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5677 4.5553 -0.0321 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5426 7.9536 1.3548 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6197 1.3626 1.0500 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5381 0.6714 0.8612 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2164 0.7369 2.2661 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1127 1.9686 2.1813 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2722 1.5174 1.3143 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6852 1.0546 0.0050 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3265 1.1518 -0.1292 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3534 -0.1266 -0.5969 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7692 -0.1194 -0.1367 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5345 -1.1210 -0.7737 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8236 -1.8490 -1.6018 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9201 -1.4603 -0.6801 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7861 -0.8100 0.0969 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1941 -1.3128 0.0413 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1359 -0.7990 0.9560 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4482 -1.1825 0.9614 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8474 -2.1151 0.0149 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9360 -2.6561 -0.9203 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6244 -2.2266 -0.8701 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3867 -3.5779 -1.8162 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6234 -4.2259 -2.7570 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1405 -2.5678 -0.0855 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4203 -0.7411 1.8253 O 0 0 0 0 0 0 0 0 0 0 0 0 12.2299 0.1576 2.8535 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2232 2.5224 1.1745 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4766 2.3273 3.4563 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0175 -0.3733 2.4275 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6575 -0.7663 3.1606 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1766 1.5799 3.3740 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8518 -2.8891 2.7319 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9873 -5.4457 2.0896 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6141 -5.8506 -0.4110 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8488 -2.4897 -1.2660 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3049 -3.4410 -1.1623 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7869 -4.1654 -1.8695 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8796 -4.4664 0.1065 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4819 -5.8190 1.3957 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0515 -4.1954 0.4638 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7030 -3.7863 2.9930 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3762 -2.0453 0.5213 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3445 0.7598 2.3144 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3171 0.0138 0.6819 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9637 -0.7179 0.9988 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0293 -0.4126 3.5152 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8007 1.3273 3.1762 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3841 -0.4685 0.9398 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2107 0.0071 -0.3544 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4236 4.1713 -4.7832 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2225 0.3804 -6.5482 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7835 -0.7624 -5.5090 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1064 3.4670 -7.3930 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0528 5.7928 -1.7985 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4484 7.8313 -0.4294 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4008 5.6139 1.4392 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9502 3.6453 0.1089 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2566 7.7660 2.3240 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3997 -0.4217 0.7387 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5171 0.8180 3.0712 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5743 2.7867 1.6329 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7558 0.6401 1.8096 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0361 1.9302 -0.7147 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5040 -0.0829 -1.7063 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9132 -1.1011 -0.3543 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2993 -2.3513 -1.1880 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4974 0.0019 0.7030 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7798 -0.0791 1.6663 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9785 -2.6691 -1.6286 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2612 -4.7048 -3.5766 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8795 -3.6147 -3.2946 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0494 -5.1175 -2.3485 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7814 -2.0649 -0.7341 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9222 1.1729 2.5017 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5590 -0.2028 3.6746 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2001 0.3681 3.4090 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1391 2.8764 0.2409 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7705 1.5009 3.9193 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7248 -1.0377 1.7210 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5413 -0.5730 4.1250 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7380 1.4275 4.1728 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5008 -3.5146 3.4063 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5727 -5.8817 2.7631 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3833 -5.9972 -1.0021 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 24 28 1 0 22 29 1 0 18 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 33 36 1 0 13 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 45 46 1 0 46 47 2 0 46 48 1 0 48 49 2 3 49 50 1 0 50 51 2 0 51 52 1 0 52 53 2 0 53 54 1 0 54 55 2 0 54 56 1 0 56 57 1 0 53 58 1 0 52 59 1 0 59 60 1 0 41 61 1 0 40 62 1 0 39 63 1 0 12 64 1 0 11 65 1 0 5 66 1 0 4 67 1 0 3 68 1 0 7 2 1 0 15 10 1 0 26 17 1 0 25 20 1 0 35 30 1 0 43 38 1 0 55 50 1 0 1 69 1 0 1 70 1 0 1 71 1 0 2 72 1 0 3 73 1 0 4 74 1 0 5 75 1 0 6 76 1 0 9 77 1 0 9 78 1 0 10 79 1 0 11 80 1 0 12 81 1 0 13 82 1 0 14 83 1 0 21 84 1 0 23 85 1 0 28 86 1 0 29 87 1 0 31 88 1 0 32 89 1 0 34 90 1 0 35 91 1 0 36 92 1 0 38 93 1 0 39 94 1 0 40 95 1 0 41 96 1 0 42 97 1 0 44 98 1 0 44 99 1 0 48100 1 0 49101 1 0 51102 1 0 55103 1 0 57104 1 0 57105 1 0 57106 1 0 58107 1 0 60108 1 0 60109 1 0 60110 1 0 61111 1 0 62112 1 0 63113 1 0 64114 1 0 65115 1 0 66116 1 0 67117 1 0 68118 1 0 M END

Standard InCHIKey	DZPPRTIRIIWSHG-HZYXUECESA-N
Standard InCHI	InChI=1S/C44H50O24/c1-16-29(49)34(54)37(57)42(63-16)62-15-26-32(52)36(56)41(44(66-26)67-40-33(53)28-21(47)12-20(46)13-22(28)64-39(40)18-5-7-19(45)8-6-18)68-43-38(58)35(55)31(51)25(65-43)14-61-27(48)9-4-17-10-23(59-2)30(50)24(11-17)60-3/h4-13,16,25-26,29,31-32,34-38,41-47,49-52,54-58H,14-15H2,1-3H3/b9-4+/t16-,25+,26+,29-,31+,32+,34+,35-,36-,37+,38+,41+,42+,43-,44-/m0/s1
SMILES	CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)OC6C(C(C(C(O6)COC(=O)C=CC7=CC(=C(C(=C7)OC)O)OC)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	962.27	Volume:	886.376 ? Van der Waals volume.
Dense:	1.086	LogP:	0.144 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.627 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.254 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	44.0
TPSA:	373.11 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	12.0	Rings:	7.0
Heavy Atoms:	24.0

MedChem Properties

QED Drug-Likeness Score:	0.05	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.764	Fsp³:	0.455
MCE-18:	173.438 ? 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:	0
Colloidal aggregators:	0.478	Fluc inhibitor:	0.349 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.721 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.979 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.324	Promiscuous compounds:	0.466

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.107	MDCK Permeability:	-5.268
Pgp-inhibitor:	0.0	Pgp-substrate:	0.988
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):	0.99
20% Bioavailability (F20%):	0.891	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.957
Plasma Protein Binding (PPB):	79.997%	Volume Distribution (VD):	-0.179
Fu:	19.112% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.004
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.715
BSEP inhibitor:	0.425

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.074	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:	1.0
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):

0.749

Half-life (T1/2):

4.71

ADMET: Toxicity

hERG Blockers:	0.044	hERG Blockers (10um):	0.629
Human Hepatotoxicity (H-HT):	0.232	Drug-induced Liver Injury (DILI):	0.842
AMES Toxicity:	0.829	Rat Oral Acute Toxicity:	0.386
Maximum Recommended Daily Dose:	0.861	Skin Sensitization:	0.366
Carcinogencity:	0.075	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.165	Ototoxicity:	0.986
Hematotoxicity:	0.002	Drug-induced Nephrotoxicity:	0.016
Genotoxicity:	0.812	RPMI-8226 Immunitoxicity:	0.206
A549 Cytotoxicity:	0.407	Hek293 Cytotoxicity:	0.993
BCF:	0.419 ? 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:	3.174 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.117 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.068 ? 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
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	leaves	n.a.	n.a.	PMID[11170659]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12502329]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27323	Cestrum nocturnum	Species	Solanaceae	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 NPC473554 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	17303
0.1-0.2	28264
0.2-0.3	3423
0.3-0.4	504
0.4-0.5	193
0.5-0.6	102
0.6-0.7	52
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8051	Intermediate Similarity	NPC487500
0.7807	Intermediate Similarity	NPC25946
0.767	Intermediate Similarity	NPC12013
0.767	Intermediate Similarity	NPC11432
0.767	Intermediate Similarity	NPC477613
0.7398	Intermediate Similarity	NPC487501
0.7339	Intermediate Similarity	NPC89052
0.7315	Intermediate Similarity	NPC602448
0.7288	Intermediate Similarity	NPC21359
0.7288	Intermediate Similarity	NPC460984
0.7222	Intermediate Similarity	NPC221342
0.7222	Intermediate Similarity	NPC476470
0.7217	Intermediate Similarity	NPC162394
0.7131	Intermediate Similarity	NPC487502
0.7103	Intermediate Similarity	NPC122467
0.6903	Remote Similarity	NPC173837
0.6847	Remote Similarity	NPC218161
0.6727	Remote Similarity	NPC142142
0.6695	Remote Similarity	NPC480445
0.6667	Remote Similarity	NPC89127
0.661	Remote Similarity	NPC488734
0.661	Remote Similarity	NPC488735
0.661	Remote Similarity	NPC488739
0.661	Remote Similarity	NPC488732
0.661	Remote Similarity	NPC488738
0.6571	Remote Similarity	NPC476215
0.6518	Remote Similarity	NPC85751
0.6518	Remote Similarity	NPC19240
0.6481	Remote Similarity	NPC173582
0.6481	Remote Similarity	NPC265885
0.6481	Remote Similarity	NPC181465
0.6481	Remote Similarity	NPC215710
0.6481	Remote Similarity	NPC473438
0.6481	Remote Similarity	NPC253788
0.648	Remote Similarity	NPC231787
0.646	Remote Similarity	NPC292929
0.641	Remote Similarity	NPC303694
0.6393	Remote Similarity	NPC488737
0.6348	Remote Similarity	NPC214621
0.6348	Remote Similarity	NPC34267
0.6339	Remote Similarity	NPC473327
0.633	Remote Similarity	NPC163242
0.633	Remote Similarity	NPC272068
0.6311	Remote Similarity	NPC480444
0.6279	Remote Similarity	NPC249560
0.6271	Remote Similarity	NPC217520
0.625	Remote Similarity	NPC72554
0.623	Remote Similarity	NPC488740
0.623	Remote Similarity	NPC488736
0.623	Remote Similarity	NPC488733
0.6228	Remote Similarity	NPC476472
0.6228	Remote Similarity	NPC294815
0.6228	Remote Similarity	NPC16194
0.621	Remote Similarity	NPC192539
0.6186	Remote Similarity	NPC477895
0.6142	Remote Similarity	NPC487499
0.6124	Remote Similarity	NPC30011
0.6121	Remote Similarity	NPC223426
0.6098	Remote Similarity	NPC474522
0.6094	Remote Similarity	NPC275977
0.6087	Remote Similarity	NPC220173
0.6061	Remote Similarity	NPC97817
0.6055	Remote Similarity	NPC95866
0.6033	Remote Similarity	NPC139571
0.6	Remote Similarity	NPC209550
0.6	Remote Similarity	NPC25523
0.6	Remote Similarity	NPC241781
0.5982	Remote Similarity	NPC203259
0.5982	Remote Similarity	NPC33054
0.5982	Remote Similarity	NPC176740
0.5982	Remote Similarity	NPC471725
0.5982	Remote Similarity	NPC134532
0.5982	Remote Similarity	NPC602582
0.5966	Remote Similarity	NPC470416
0.5932	Remote Similarity	NPC81042
0.5841	Remote Similarity	NPC155877
0.584	Remote Similarity	NPC156785
0.5827	Remote Similarity	NPC480443
0.5818	Remote Similarity	NPC170052
0.5818	Remote Similarity	NPC135846
0.5806	Remote Similarity	NPC474093
0.5806	Remote Similarity	NPC104910
0.5789	Remote Similarity	NPC473571
0.5789	Remote Similarity	NPC110941
0.5763	Remote Similarity	NPC36138
0.575	Remote Similarity	NPC203145
0.5702	Remote Similarity	NPC304741
0.5664	Remote Similarity	NPC471079
0.5652	Remote Similarity	NPC470444
0.5635	Remote Similarity	NPC470713
0.5614	Remote Similarity	NPC470405
0.5614	Remote Similarity	NPC39834
0.5603	Remote Similarity	NPC240306
0.5603	Remote Similarity	NPC153755
0.5596	Remote Similarity	NPC216496
0.5593	Remote Similarity	NPC603079
0.5574	Remote Similarity	NPC189564
0.5537	Remote Similarity	NPC96605
0.5537	Remote Similarity	NPC280642
0.5526	Remote Similarity	NPC609888
0.5484	Remote Similarity	NPC480441
0.5462	Remote Similarity	NPC221288
0.5462	Remote Similarity	NPC194836
0.5462	Remote Similarity	NPC91493
0.5462	Remote Similarity	NPC605081
0.5461	Remote Similarity	NPC33083
0.5431	Remote Similarity	NPC65563
0.5431	Remote Similarity	NPC470949
0.542	Remote Similarity	NPC480442
0.5417	Remote Similarity	NPC471669
0.541	Remote Similarity	NPC478277
0.541	Remote Similarity	NPC478276
0.541	Remote Similarity	NPC478275
0.541	Remote Similarity	NPC92815
0.5397	Remote Similarity	NPC470718
0.5385	Remote Similarity	NPC129264
0.5385	Remote Similarity	NPC186816
0.5372	Remote Similarity	NPC260504
0.5372	Remote Similarity	NPC89809
0.537	Remote Similarity	NPC111929
0.537	Remote Similarity	NPC320283
0.537	Remote Similarity	NPC41121
0.5366	Remote Similarity	NPC11468
0.536	Remote Similarity	NPC470712
0.5351	Remote Similarity	NPC254855
0.5351	Remote Similarity	NPC116864
0.5351	Remote Similarity	NPC244776
0.5351	Remote Similarity	NPC94610
0.5339	Remote Similarity	NPC470125
0.5339	Remote Similarity	NPC126784
0.5339	Remote Similarity	NPC241423
0.5333	Remote Similarity	NPC101399
0.5333	Remote Similarity	NPC217822
0.5333	Remote Similarity	NPC11847
0.5333	Remote Similarity	NPC198938
0.5328	Remote Similarity	NPC483767
0.5328	Remote Similarity	NPC483769
0.5328	Remote Similarity	NPC483768
0.5328	Remote Similarity	NPC483766
0.5299	Remote Similarity	NPC156869
0.5289	Remote Similarity	NPC477629
0.5285	Remote Similarity	NPC483765
0.5268	Remote Similarity	NPC219904
0.5254	Remote Similarity	NPC255157
0.5254	Remote Similarity	NPC259896
0.525	Remote Similarity	NPC270448
0.525	Remote Similarity	NPC104883
0.525	Remote Similarity	NPC488679
0.5221	Remote Similarity	NPC224530
0.5214	Remote Similarity	NPC67326
0.5207	Remote Similarity	NPC97119
0.5175	Remote Similarity	NPC223747
0.5164	Remote Similarity	NPC470447
0.5164	Remote Similarity	NPC76831
0.5159	Remote Similarity	NPC219043
0.5159	Remote Similarity	NPC292019
0.5159	Remote Similarity	NPC48984
0.5159	Remote Similarity	NPC202908
0.5154	Remote Similarity	NPC298666
0.5128	Remote Similarity	NPC187379
0.5126	Remote Similarity	NPC35167
0.5124	Remote Similarity	NPC32641
0.5124	Remote Similarity	NPC256188
0.5115	Remote Similarity	NPC470717
0.5083	Remote Similarity	NPC61904
0.5076	Remote Similarity	NPC470720
0.5041	Remote Similarity	NPC470443
0.5039	Remote Similarity	NPC480796
0.5038	Remote Similarity	NPC120952

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473554 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5165
0.1-0.2	3933
0.2-0.3	44
0.3-0.4	3
0.4-0.5	4
0.5-0.6	1
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
0.5982	Remote Similarity	NPD6797	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