NPASS Compound

Natural Product: NPC249524

Natural Product ID	NPC249524
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SHRUKDVTMUBNTL-XJRUTDMXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10191345
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 111117 0 0 0 0 0 0 0 0999 V2000 -0.9566 -6.8707 0.2878 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0646 -5.6583 0.4182 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2628 -6.0006 -0.2516 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7792 -4.7566 -0.9634 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4229 -3.6087 0.0016 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0552 -3.3871 -0.1519 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6833 -4.6049 -0.2413 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6184 -2.5764 0.8713 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5868 -1.6011 0.5553 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1436 -0.3569 0.0886 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0789 -0.1125 -0.0399 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0468 0.6237 -0.2384 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6783 1.8646 -0.7032 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6101 2.8233 -1.0227 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9894 2.5765 -0.8876 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3296 1.3312 -0.4223 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3873 0.3459 -0.0936 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7506 -0.8142 0.3418 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9305 -1.8195 0.6825 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5364 -3.0508 1.1569 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8803 -3.2499 0.9422 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5358 -4.3602 1.4194 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8620 -5.3081 2.1290 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5248 -5.1314 2.3555 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8662 -3.9922 1.8628 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8181 -6.0696 3.0671 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4837 -6.4277 2.6191 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8890 3.5714 -1.2214 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2725 3.5137 -1.1340 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8490 4.5842 -0.2235 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9276 5.3716 -0.9446 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9265 4.4340 -1.5975 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1783 3.4778 -2.4799 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5597 3.8322 -3.9257 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9388 3.7508 -4.1016 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8164 3.5947 -2.4131 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5921 3.6690 -0.6249 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3433 6.1944 -1.8823 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3101 4.0272 0.9656 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3158 2.1210 -0.8414 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2489 -2.5819 -0.3215 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1213 -2.2082 0.7142 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5507 -2.4489 0.3666 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4107 -1.9882 1.5349 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1148 -0.5449 1.8379 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9599 -0.0445 1.0963 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1854 0.7797 -0.1112 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3229 1.5510 -0.2302 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6164 1.1548 -0.5006 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8265 -0.0720 -0.6959 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7458 2.1083 -0.5686 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5118 3.3678 -0.3627 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5529 4.3638 -0.4105 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8559 4.0335 -0.6840 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8455 5.0292 -0.7207 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5197 6.3375 -0.4843 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2080 6.6780 -0.2079 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2350 5.6931 -0.1725 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4927 7.3199 -0.5204 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8633 -0.8913 0.9940 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8198 -0.4084 3.2307 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7412 -2.2867 1.4039 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8380 -3.8262 0.2580 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9394 -4.5872 -2.0784 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1698 -6.3186 0.7468 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0187 -7.4336 1.2434 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9971 -6.5630 -0.0266 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5801 -7.5186 -0.5179 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0624 -5.4466 1.4873 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1419 -6.8670 -0.9042 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8157 -4.7854 -1.2467 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5604 -3.9953 1.0368 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2844 -2.8668 -1.1172 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3186 3.7919 -1.3856 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3619 1.0639 -0.2911 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4450 -2.5196 0.3831 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6084 -4.5038 1.2389 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8225 -3.9275 2.1056 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2609 -5.9269 3.8791 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9872 -7.0290 1.9629 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5861 2.5412 -0.7229 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0253 5.2759 0.0349 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4682 5.9611 -0.1838 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6246 5.0519 -2.1573 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5199 2.4242 -2.3218 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0125 3.1766 -4.6313 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2211 4.8771 -4.0620 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2198 2.8581 -3.7545 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5609 3.8608 -0.6837 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1901 7.0948 -1.5058 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8754 3.1759 1.1791 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0126 3.0854 -0.8870 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9131 -2.8364 1.6247 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8328 -2.0319 -0.5952 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 -2.5755 2.4241 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0045 0.0767 1.6913 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4990 0.7690 1.8439 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3161 1.5271 -0.2270 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1557 0.1281 -1.0495 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7040 1.7081 -0.7868 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4703 3.6630 -0.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1763 3.0185 -0.8799 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8852 4.7758 -0.9380 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9637 7.7166 -0.0233 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2119 5.9491 0.0420 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4693 7.1398 -0.2621 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5676 0.5463 3.3336 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1731 -2.4569 2.2787 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7675 -3.9587 -0.0421 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4378 -4.2442 -2.8617 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8437 -5.9295 1.5926 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 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 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 24 26 1 0 23 27 1 0 15 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 32 37 1 0 31 38 1 0 30 39 1 0 13 40 1 0 5 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 2 0 49 51 1 0 51 52 2 0 52 53 1 0 53 54 2 0 54 55 1 0 55 56 2 0 56 57 1 0 57 58 2 0 56 59 1 0 46 60 1 0 45 61 1 0 44 62 1 0 43 63 1 0 4 64 1 0 3 65 1 0 7 2 1 0 19 9 2 0 25 20 1 0 36 29 1 0 60 42 1 0 17 12 1 0 58 53 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 6 5 72 1 1 6 73 1 6 14 74 1 0 16 75 1 0 21 76 1 0 22 77 1 0 25 78 1 0 26 79 1 0 27 80 1 0 29 81 1 1 30 82 1 1 31 83 1 1 32 84 1 6 33 85 1 1 34 86 1 0 34 87 1 0 35 88 1 0 37 89 1 0 38 90 1 0 39 91 1 0 40 92 1 0 42 93 1 1 43 94 1 6 44 95 1 1 45 96 1 6 46 97 1 1 47 98 1 0 47 99 1 0 51100 1 0 52101 1 0 54102 1 0 55103 1 0 57104 1 0 58105 1 0 59106 1 0 61107 1 0 62108 1 0 63109 1 0 64110 1 0 65111 1 0 M END

Standard InCHIKey	SHRUKDVTMUBNTL-XJRUTDMXSA-N
Standard InCHI	InChI=1S/C42H46O23/c1-15-28(49)34(55)39(65-41-36(57)33(54)30(51)25(63-41)14-58-26(48)9-4-16-2-6-18(44)7-3-16)42(59-15)64-38-31(52)27-22(47)11-19(60-40-35(56)32(53)29(50)24(13-43)62-40)12-23(27)61-37(38)17-5-8-20(45)21(46)10-17/h2-12,15,24-25,28-30,32-36,39-47,49-51,53-57H,13-14H2,1H3/b9-4+/t15-,24+,25+,28-,29+,30+,32-,33-,34+,35+,36+,39+,40+,41-,42-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(c(c1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)/C=C/c2ccc(cc2)O)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	918.24	Volume:	842.994 ? Van der Waals volume.
Dense:	1.089	LogP:	1.089 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.488 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.045 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	44.0
TPSA:	374.88 ? Topological Polar Surface Area.	H-Bond Acceptor:	23.0
H-Bond Donor:	13.0	Rings:	7.0
Heavy Atoms:	23.0

MedChem Properties

QED Drug-Likeness Score:	0.041	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.69	Fsp³:	0.429
MCE-18:	171.5 ? 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:	0.686	Fluc inhibitor:	0.613 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.778 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.666 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.3	Promiscuous compounds:	0.6

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.755	MDCK Permeability:	-4.956
Pgp-inhibitor:	0.0	Pgp-substrate:	0.06
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):	0.983
20% Bioavailability (F20%):	0.953	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):	80.881%	Volume Distribution (VD):	-0.102
Fu:	17.117% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.008
BSEP inhibitor:	0.001

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:	0.985
HLM stability:	0.008 ? 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):

1.007

Half-life (T1/2):

6.936

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.051
Human Hepatotoxicity (H-HT):	0.535	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.984	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.009	Skin Sensitization:	1.0
Carcinogencity:	0.016	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.045	Drug-induced Nephrotoxicity:	0.762
Genotoxicity:	0.933	RPMI-8226 Immunitoxicity:	0.135
A549 Cytotoxicity:	0.952	Hek293 Cytotoxicity:	0.804
BCF:	0.52 ? 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:	3.295 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.986 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.241 ? 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
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	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 NPC249524 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	18120
0.1-0.2	26924
0.2-0.3	3691
0.3-0.4	646
0.4-0.5	307
0.5-0.6	120
0.6-0.7	36
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	Natural Product ID
0.7321	Intermediate Similarity	NPC480441
0.7168	Intermediate Similarity	NPC164704
0.7018	Intermediate Similarity	NPC470715
0.7018	Intermediate Similarity	NPC25523
0.6885	Remote Similarity	NPC21359
0.6885	Remote Similarity	NPC460984
0.6814	Remote Similarity	NPC14187
0.68	Remote Similarity	NPC223860
0.6667	Remote Similarity	NPC35119
0.6579	Remote Similarity	NPC223426
0.6532	Remote Similarity	NPC25946
0.6529	Remote Similarity	NPC470717
0.6518	Remote Similarity	NPC32641
0.6518	Remote Similarity	NPC256188
0.6393	Remote Similarity	NPC488740
0.6341	Remote Similarity	NPC470720
0.6341	Remote Similarity	NPC488078
0.6333	Remote Similarity	NPC470716
0.6316	Remote Similarity	NPC270675
0.6316	Remote Similarity	NPC195685
0.6308	Remote Similarity	NPC249560
0.6261	Remote Similarity	NPC80068
0.626	Remote Similarity	NPC162394
0.626	Remote Similarity	NPC470719
0.626	Remote Similarity	NPC488736
0.626	Remote Similarity	NPC488733
0.6231	Remote Similarity	NPC487502
0.623	Remote Similarity	NPC295625
0.6204	Remote Similarity	NPC605784
0.6195	Remote Similarity	NPC240306
0.6195	Remote Similarity	NPC64425
0.616	Remote Similarity	NPC488737
0.6121	Remote Similarity	NPC85751
0.6121	Remote Similarity	NPC19240
0.6102	Remote Similarity	NPC81042
0.6038	Remote Similarity	NPC136042
0.6034	Remote Similarity	NPC142142
0.6033	Remote Similarity	NPC470712
0.6017	Remote Similarity	NPC472994
0.6	Remote Similarity	NPC473554
0.5968	Remote Similarity	NPC488739
0.5935	Remote Similarity	NPC470718
0.5909	Remote Similarity	NPC116458
0.5909	Remote Similarity	NPC246943
0.5906	Remote Similarity	NPC209550
0.584	Remote Similarity	NPC488734
0.584	Remote Similarity	NPC488735
0.584	Remote Similarity	NPC488732
0.584	Remote Similarity	NPC488738
0.5833	Remote Similarity	NPC214621
0.5833	Remote Similarity	NPC34267
0.5833	Remote Similarity	NPC84362
0.5826	Remote Similarity	NPC186816
0.582	Remote Similarity	NPC472993
0.582	Remote Similarity	NPC477895
0.5798	Remote Similarity	NPC36138
0.5772	Remote Similarity	NPC217520
0.5752	Remote Similarity	NPC251417
0.575	Remote Similarity	NPC218161
0.5741	Remote Similarity	NPC297987
0.5703	Remote Similarity	NPC488079
0.5691	Remote Similarity	NPC480796
0.5678	Remote Similarity	NPC139060
0.5672	Remote Similarity	NPC30011
0.5669	Remote Similarity	NPC298666
0.5652	Remote Similarity	NPC487501
0.5625	Remote Similarity	NPC156785
0.562	Remote Similarity	NPC602448
0.5603	Remote Similarity	NPC155877
0.5556	Remote Similarity	NPC115674
0.5546	Remote Similarity	NPC122467
0.5545	Remote Similarity	NPC271692
0.5538	Remote Similarity	NPC241781
0.5526	Remote Similarity	NPC254855
0.5526	Remote Similarity	NPC94610
0.5526	Remote Similarity	NPC95866
0.5505	Remote Similarity	NPC289667
0.5493	Remote Similarity	NPC33083
0.5478	Remote Similarity	NPC8856
0.5476	Remote Similarity	NPC277532
0.547	Remote Similarity	NPC156869
0.5468	Remote Similarity	NPC487500
0.5462	Remote Similarity	NPC480444
0.5441	Remote Similarity	NPC72554
0.5433	Remote Similarity	NPC139571
0.5426	Remote Similarity	NPC470713
0.5407	Remote Similarity	NPC275977
0.5403	Remote Similarity	NPC121703
0.5379	Remote Similarity	NPC192539
0.5372	Remote Similarity	NPC486577
0.5366	Remote Similarity	NPC135358
0.5364	Remote Similarity	NPC249281
0.536	Remote Similarity	NPC470416
0.5339	Remote Similarity	NPC65003
0.5339	Remote Similarity	NPC210073
0.5328	Remote Similarity	NPC473071
0.5328	Remote Similarity	NPC477629
0.5317	Remote Similarity	NPC292019
0.5317	Remote Similarity	NPC202908
0.5304	Remote Similarity	NPC276377
0.5303	Remote Similarity	NPC120952
0.5294	Remote Similarity	NPC231787
0.5286	Remote Similarity	NPC97817
0.5268	Remote Similarity	NPC46420
0.5259	Remote Similarity	NPC116864
0.5259	Remote Similarity	NPC244776
0.5254	Remote Similarity	NPC163242
0.5254	Remote Similarity	NPC272068
0.5254	Remote Similarity	NPC67105
0.525	Remote Similarity	NPC488073
0.5231	Remote Similarity	NPC68592
0.521	Remote Similarity	NPC203259
0.521	Remote Similarity	NPC33054
0.521	Remote Similarity	NPC176740
0.521	Remote Similarity	NPC471725
0.521	Remote Similarity	NPC134532
0.521	Remote Similarity	NPC150164
0.521	Remote Similarity	NPC602582
0.5207	Remote Similarity	NPC12013
0.5207	Remote Similarity	NPC11432
0.5207	Remote Similarity	NPC477613
0.5203	Remote Similarity	NPC471669
0.5203	Remote Similarity	NPC76831
0.5203	Remote Similarity	NPC89127
0.52	Remote Similarity	NPC603856
0.5191	Remote Similarity	NPC198199
0.5191	Remote Similarity	NPC480445
0.5185	Remote Similarity	NPC199172
0.5179	Remote Similarity	NPC277205
0.5179	Remote Similarity	NPC37919
0.5179	Remote Similarity	NPC189142
0.5179	Remote Similarity	NPC77660
0.5175	Remote Similarity	NPC611303
0.5172	Remote Similarity	NPC170052
0.5172	Remote Similarity	NPC476215
0.5172	Remote Similarity	NPC135846
0.5167	Remote Similarity	NPC255157
0.5167	Remote Similarity	NPC259896
0.5164	Remote Similarity	NPC72016
0.5161	Remote Similarity	NPC292929
0.5159	Remote Similarity	NPC11468
0.5156	Remote Similarity	NPC303694
0.5149	Remote Similarity	NPC175429
0.5126	Remote Similarity	NPC44931
0.5116	Remote Similarity	NPC311850
0.5111	Remote Similarity	NPC480472
0.5085	Remote Similarity	NPC473682
0.5082	Remote Similarity	NPC470443
0.5082	Remote Similarity	NPC483414
0.5078	Remote Similarity	NPC219043
0.5044	Remote Similarity	NPC145038
0.5044	Remote Similarity	NPC56077
0.5044	Remote Similarity	NPC281131
0.5044	Remote Similarity	NPC253662
0.5044	Remote Similarity	NPC179950
0.5044	Remote Similarity	NPC88789
0.5044	Remote Similarity	NPC491374
0.5041	Remote Similarity	NPC470444
0.504	Remote Similarity	NPC470445
0.5039	Remote Similarity	NPC599948

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC249524 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4933
0.1-0.2	4161
0.2-0.3	46
0.3-0.4	4
0.4-0.5	3
0.5-0.6	3
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
0.5847	Remote Similarity	NPD7251	Phase 2
0.521	Remote Similarity	NPD6797	Phase 2
0.5159	Remote Similarity	NPD7808	Phase 3

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