NPASS Compound

Natural Product: NPC581317

Natural Product ID	NPC581317
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	quercetin 3-O-[alpha-rhamnosyl (1â†’6)] [beta-glucosyl (1â†’2)]-beta-glucoside-7-O-alpha-rhamnoside
IUPAC Name	2-(3,4-dihydroxyphenyl)-3-[(3~{R},4~{S},5~{R},6~{R})-3,5-dihydroxy-4-[(3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-[[(3~{S},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-5-hydroxy-7-[(3~{S},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 -4.5144 3.4323 2.6652 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6328 3.7418 1.2142 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5637 2.5733 0.4590 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3280 2.8482 -0.8918 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0309 2.9287 -1.1658 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2877 2.1104 -1.8930 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0504 0.7661 -1.3270 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4596 0.9124 -0.0559 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9445 -0.3531 0.2391 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0441 -0.3741 1.3248 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3323 -0.4098 1.1590 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0834 0.7261 1.2229 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5913 2.0585 1.4817 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3746 2.3834 1.9692 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0510 3.7013 2.1586 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7919 4.7289 1.8418 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3822 6.0635 2.0250 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0414 4.4387 1.3432 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8719 5.5037 1.0326 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4354 3.1305 1.1659 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3989 0.5500 1.0243 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9620 -0.5989 0.7893 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3374 -0.7046 0.5941 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0006 -1.8742 0.3443 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3613 -1.9663 0.1530 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3133 -0.9507 0.1716 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2668 -1.2809 1.1127 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3546 -0.4568 1.1563 C 0 0 2 0 0 0 0 0 0 0 0 0 10.1111 0.7902 2.0095 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9373 -0.1039 -0.1809 C 0 0 1 0 0 0 0 0 0 0 0 0 11.5513 -1.2625 -0.6768 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8875 0.3036 -1.1903 C 0 0 2 0 0 0 0 0 0 0 0 0 9.2398 1.4435 -0.7396 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8846 -0.8540 -1.2279 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8310 -0.4896 -2.0744 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2056 -3.0278 0.2879 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8449 -2.9889 0.4717 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0313 -4.0904 0.4248 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2259 -1.7596 0.7241 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8825 -1.6668 0.9125 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2195 -2.7241 0.8520 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1293 -1.2296 0.5165 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7475 -2.3369 1.2080 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7650 -1.5608 -0.8543 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9199 -2.2687 -0.7029 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9804 -3.4790 -1.3330 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9234 -4.4377 -0.3204 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0754 -4.6281 0.3822 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9563 -5.7344 1.4155 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1738 -5.8660 2.0843 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3077 -4.8681 -0.4743 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4684 -4.8389 0.2965 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4523 -3.8144 -1.5373 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3859 -4.2976 -2.4607 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1212 -3.6972 -2.2642 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2750 -2.7571 -3.2571 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2002 -0.1440 -1.3412 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7554 -0.1930 -2.5842 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1275 4.0762 -1.2821 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4732 4.0829 -2.6202 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4046 4.0973 -0.4751 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8900 2.7819 -0.4350 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9819 4.4190 0.9761 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7752 5.7858 1.0269 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8831 2.4470 2.9553 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4779 3.5964 3.0429 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1368 4.1840 3.2289 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8591 4.4292 0.8583 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8144 2.0013 -1.4351 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6665 1.9866 -2.9647 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2506 2.5478 -2.0823 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2259 0.2690 -1.9971 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4668 -0.6817 -0.7075 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3294 1.6251 2.2628 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0295 3.9458 2.5490 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7546 6.5517 2.8482 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8571 5.3382 0.7987 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4365 2.9579 0.7680 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8798 0.2284 0.6522 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8219 0.0145 0.3658 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1661 -1.0144 1.7122 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1151 1.2672 2.1156 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3554 1.4537 1.5930 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8296 0.4561 3.0292 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7076 0.6711 -0.0315 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6504 -1.2100 -1.6780 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3808 0.4401 -2.1606 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3629 2.2146 -1.3423 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3908 -1.7707 -1.5561 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0846 -0.7543 -3.0115 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6902 -3.9718 0.0931 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5612 -4.2955 -0.4566 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8788 -0.6767 1.1356 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5067 -3.1148 0.6609 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9809 -1.9775 -1.4689 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0313 -3.6298 -1.9062 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2809 -3.6971 0.9624 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6887 -6.6992 0.9857 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1929 -5.4798 2.1806 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4651 -6.8114 2.1280 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2009 -5.8464 -0.9590 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1208 -5.5203 -0.0177 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7088 -2.8304 -1.1524 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9498 -4.6824 -3.2513 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0199 -4.6855 -2.8064 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4177 -3.0988 -4.1558 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9602 0.1423 -0.5938 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1395 -0.0400 -3.3277 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5410 4.9942 -1.0484 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3624 4.4973 -2.7340 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1502 4.8083 -0.8396 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7665 2.6924 -0.8588 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7476 4.1426 1.7058 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3489 6.2960 0.4111 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 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 16 18 1 0 18 19 1 0 18 20 2 0 12 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 24 36 2 0 36 37 1 0 37 38 1 0 37 39 2 0 39 40 1 0 40 41 2 0 9 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 48 51 1 0 51 52 1 0 51 53 1 0 53 54 1 0 53 55 1 0 55 56 1 0 44 57 1 0 57 58 1 0 4 59 1 0 59 60 1 0 59 61 1 0 61 62 1 0 61 63 1 0 63 64 1 0 63 2 1 0 57 7 1 0 40 11 1 0 55 46 1 0 20 13 1 0 39 22 1 0 34 26 1 0 1 65 1 0 1 66 1 0 1 67 1 0 2 68 1 6 4 69 1 0 6 70 1 0 6 71 1 0 7 72 1 6 9 73 1 0 14 74 1 0 15 75 1 0 17 76 1 0 19 77 1 0 20 78 1 0 23 79 1 0 26 80 1 0 28 81 1 1 29 82 1 0 29 83 1 0 29 84 1 0 30 85 1 1 31 86 1 0 32 87 1 6 33 88 1 0 34 89 1 6 35 90 1 0 36 91 1 0 38 92 1 0 42 93 1 1 43 94 1 0 44 95 1 6 46 96 1 0 48 97 1 1 49 98 1 0 49 99 1 0 50100 1 0 51101 1 6 52102 1 0 53103 1 1 54104 1 0 55105 1 6 56106 1 0 57107 1 1 58108 1 0 59109 1 1 60110 1 0 61111 1 6 62112 1 0 63113 1 1 64114 1 0 M END

Standard InCHIKey	JOXXHKHYJZQZDC-BISWWVLVSA-N
Standard InCHI	InChI=1S/C39H50O25/c1-10-21(44)26(49)29(52)36(57-10)56-9-19-24(47)34(63-38-31(54)28(51)23(46)18(8-40)61-38)32(55)39(62-19)64-35-25(48)20-16(43)6-13(59-37-30(53)27(50)22(45)11(2)58-37)7-17(20)60-33(35)12-3-4-14(41)15(42)5-12/h3-7,10-11,18-19,21-24,26-32,34,36-47,49-55H,8-9H2,1-2H3/t10-,11-,18-,19-,21-,22-,23-,24-,26+,27+,28+,29+,30+,31-,32-,34+,36?,37?,38?,39?/m1/s1
SMILES	C[C@H]1OC(OC[C@H]2OC(OC3=C(C4=CC=C(O)C(O)=C4)OC4=CC(OC5O[C@H](C)[C@@H](O)[C@H](O)[C@@H]5O)=CC(O)=C4C3=O)[C@H](O)[C@@H](OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]2O)[C@@H](O)[C@@H](O)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	918.26	Volume:	821.869 ? Van der Waals volume.
Dense:	1.117	LogP:	-1.639 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.133 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.127 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	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:	5.959	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:	0.628	Fluc inhibitor:	0.248 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.753 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.653 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.34	Promiscuous compounds:	0.468

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.15	MDCK Permeability:	-4.648
Pgp-inhibitor:	0.0	Pgp-substrate:	0.967
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):	0.979
20% Bioavailability (F20%):	0.486	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.009
Plasma Protein Binding (PPB):	67.257%	Volume Distribution (VD):	-0.213
Fu:	28.327% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.049
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:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.026
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.245
HLM stability:	0.023 ? 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):

0.069

Half-life (T1/2):

6.806

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.072
Human Hepatotoxicity (H-HT):	0.317	Drug-induced Liver Injury (DILI):	0.985
AMES Toxicity:	0.964	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.003	Skin Sensitization:	1.0
Carcinogencity:	0.006	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.052	Drug-induced Nephrotoxicity:	0.738
Genotoxicity:	0.752	RPMI-8226 Immunitoxicity:	0.2
A549 Cytotoxicity:	0.866	Hek293 Cytotoxicity:	0.287
BCF:	0.326 ? 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:	2.696 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.478 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.5 ? 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
NPO48896	Warburgia ugandensis	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC581317 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	25478
0.1-0.2	20452
0.2-0.3	3121
0.3-0.4	365
0.4-0.5	250
0.5-0.6	127
0.6-0.7	43
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	Natural Product ID
0.7723	Intermediate Similarity	NPC480441
0.7582	Intermediate Similarity	NPC605784
0.7426	Intermediate Similarity	NPC203145
0.7396	Intermediate Similarity	NPC186816
0.7282	Intermediate Similarity	NPC292019
0.7282	Intermediate Similarity	NPC202908
0.7157	Intermediate Similarity	NPC14187
0.7048	Intermediate Similarity	NPC25523
0.7033	Intermediate Similarity	NPC136042
0.6957	Remote Similarity	NPC271692
0.6842	Remote Similarity	NPC116458
0.6842	Remote Similarity	NPC246943
0.6698	Remote Similarity	NPC189564
0.6667	Remote Similarity	NPC67105
0.66	Remote Similarity	NPC203259
0.66	Remote Similarity	NPC33054
0.66	Remote Similarity	NPC210073
0.66	Remote Similarity	NPC176740
0.66	Remote Similarity	NPC471725
0.66	Remote Similarity	NPC134532
0.66	Remote Similarity	NPC156869
0.66	Remote Similarity	NPC602582
0.6596	Remote Similarity	NPC84362
0.6569	Remote Similarity	NPC470443
0.6505	Remote Similarity	NPC32641
0.6505	Remote Similarity	NPC256188
0.6505	Remote Similarity	NPC35119
0.6465	Remote Similarity	NPC251417
0.6383	Remote Similarity	NPC249281
0.6381	Remote Similarity	NPC473073
0.6316	Remote Similarity	NPC297987
0.6311	Remote Similarity	NPC488073
0.6311	Remote Similarity	NPC126784
0.6311	Remote Similarity	NPC241423
0.6263	Remote Similarity	NPC276377
0.625	Remote Similarity	NPC46420
0.619	Remote Similarity	NPC606657
0.6146	Remote Similarity	NPC158674
0.6132	Remote Similarity	NPC142142
0.6121	Remote Similarity	NPC241781
0.6117	Remote Similarity	NPC150164
0.6042	Remote Similarity	NPC289667
0.6019	Remote Similarity	NPC173582
0.6019	Remote Similarity	NPC44931
0.6019	Remote Similarity	NPC265885
0.6019	Remote Similarity	NPC181465
0.6019	Remote Similarity	NPC215710
0.6019	Remote Similarity	NPC275454
0.6019	Remote Similarity	NPC473438
0.6019	Remote Similarity	NPC227508
0.6019	Remote Similarity	NPC253788
0.6	Remote Similarity	NPC240306
0.596	Remote Similarity	NPC611303
0.5922	Remote Similarity	NPC480466
0.5888	Remote Similarity	NPC483416
0.5876	Remote Similarity	NPC238376
0.5865	Remote Similarity	NPC39834
0.5816	Remote Similarity	NPC277205
0.5816	Remote Similarity	NPC37919
0.581	Remote Similarity	NPC65563
0.581	Remote Similarity	NPC470949
0.5758	Remote Similarity	NPC27640
0.5741	Remote Similarity	NPC122467
0.5741	Remote Similarity	NPC72016
0.5714	Remote Similarity	NPC127546
0.5714	Remote Similarity	NPC57625
0.5714	Remote Similarity	NPC19709
0.5714	Remote Similarity	NPC67326
0.5714	Remote Similarity	NPC173637
0.5714	Remote Similarity	NPC317489
0.5714	Remote Similarity	NPC223424
0.5714	Remote Similarity	NPC600591
0.5701	Remote Similarity	NPC64425
0.5688	Remote Similarity	NPC486577
0.5676	Remote Similarity	NPC602448
0.566	Remote Similarity	NPC22062
0.566	Remote Similarity	NPC473634
0.566	Remote Similarity	NPC138811
0.566	Remote Similarity	NPC605592
0.5657	Remote Similarity	NPC145038
0.5657	Remote Similarity	NPC56077
0.5657	Remote Similarity	NPC281131
0.5657	Remote Similarity	NPC253662
0.5657	Remote Similarity	NPC179950
0.5657	Remote Similarity	NPC88789
0.5657	Remote Similarity	NPC189142
0.5657	Remote Similarity	NPC77660
0.5657	Remote Similarity	NPC491374
0.5644	Remote Similarity	NPC488071
0.5636	Remote Similarity	NPC476472
0.5636	Remote Similarity	NPC294815
0.5636	Remote Similarity	NPC16194
0.5607	Remote Similarity	NPC115674
0.5607	Remote Similarity	NPC473571
0.5607	Remote Similarity	NPC110941
0.5603	Remote Similarity	NPC470716
0.5596	Remote Similarity	NPC209296
0.5596	Remote Similarity	NPC473327
0.5586	Remote Similarity	NPC101636
0.5566	Remote Similarity	NPC471748
0.5545	Remote Similarity	NPC59534
0.5536	Remote Similarity	NPC470446
0.5514	Remote Similarity	NPC155877
0.5512	Remote Similarity	NPC249560
0.5505	Remote Similarity	NPC65711
0.5505	Remote Similarity	NPC483415
0.5495	Remote Similarity	NPC89127
0.5476	Remote Similarity	NPC223860
0.5472	Remote Similarity	NPC29958
0.5446	Remote Similarity	NPC305811
0.5429	Remote Similarity	NPC116864
0.5429	Remote Similarity	NPC244776
0.5429	Remote Similarity	NPC265115
0.5414	Remote Similarity	NPC33083
0.5413	Remote Similarity	NPC488074
0.5398	Remote Similarity	NPC135358
0.5392	Remote Similarity	NPC42773
0.5392	Remote Similarity	NPC45522
0.5392	Remote Similarity	NPC599850
0.5385	Remote Similarity	NPC277532
0.5357	Remote Similarity	NPC473071
0.5333	Remote Similarity	NPC298666
0.5328	Remote Similarity	NPC138990
0.5304	Remote Similarity	NPC121703
0.5299	Remote Similarity	NPC303694
0.5285	Remote Similarity	NPC192539
0.5254	Remote Similarity	NPC311850
0.5248	Remote Similarity	NPC108831
0.5248	Remote Similarity	NPC182634
0.5234	Remote Similarity	NPC8856
0.5234	Remote Similarity	NPC480463
0.5229	Remote Similarity	NPC479405
0.5229	Remote Similarity	NPC303913
0.5229	Remote Similarity	NPC3583
0.5225	Remote Similarity	NPC12013
0.5225	Remote Similarity	NPC483414
0.5225	Remote Similarity	NPC11432
0.5225	Remote Similarity	NPC477613
0.5221	Remote Similarity	NPC483413
0.5207	Remote Similarity	NPC198199
0.5203	Remote Similarity	NPC209550
0.5196	Remote Similarity	NPC323593
0.5196	Remote Similarity	NPC203500
0.5185	Remote Similarity	NPC471079
0.5182	Remote Similarity	NPC479404
0.5182	Remote Similarity	NPC169733
0.5175	Remote Similarity	NPC470445
0.5161	Remote Similarity	NPC175429
0.5149	Remote Similarity	NPC111929
0.5149	Remote Similarity	NPC320283
0.5149	Remote Similarity	NPC473043
0.5149	Remote Similarity	NPC331652
0.5149	Remote Similarity	NPC41121
0.5146	Remote Similarity	NPC52550
0.514	Remote Similarity	NPC254855
0.514	Remote Similarity	NPC94610
0.514	Remote Similarity	NPC95866
0.5124	Remote Similarity	NPC68592
0.512	Remote Similarity	NPC262222
0.5098	Remote Similarity	NPC39360
0.5098	Remote Similarity	NPC77672
0.5098	Remote Similarity	NPC133671
0.5098	Remote Similarity	NPC135391
0.5098	Remote Similarity	NPC29763
0.5098	Remote Similarity	NPC78263
0.5098	Remote Similarity	NPC210003
0.5098	Remote Similarity	NPC250069
0.5091	Remote Similarity	NPC293626
0.5091	Remote Similarity	NPC65003
0.5089	Remote Similarity	NPC479403
0.5088	Remote Similarity	NPC471669
0.5081	Remote Similarity	NPC120952
0.505	Remote Similarity	NPC67037
0.505	Remote Similarity	NPC255615
0.5047	Remote Similarity	NPC190003
0.5046	Remote Similarity	NPC139320
0.5044	Remote Similarity	NPC229409
0.5042	Remote Similarity	NPC164704
0.5041	Remote Similarity	NPC156785

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC581317 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6087
0.1-0.2	3002
0.2-0.3	51
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
0.7551	Intermediate Similarity	NPD7251	Phase 2
0.66	Remote Similarity	NPD6797	Phase 2
0.6449	Remote Similarity	NPD7808	Phase 3
0.5596	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