NPASS Compound

Natural Product: NPC268129

Natural Product ID	NPC268129
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WZAXZHIVHPRTIU-DKULBZLCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11972349
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001737] Flavonoid C-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 96101 0 0 0 0 0 0 0 0999 V2000 -11.5731 1.9308 0.9841 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6930 1.8101 0.0580 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6641 1.3799 -0.6449 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9022 0.2815 -0.2029 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8221 -0.2238 -0.8398 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3960 0.3378 -2.0115 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1341 1.4359 -2.4860 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2162 1.9442 -1.8507 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9480 3.0264 -2.3136 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2568 -1.4611 -0.3658 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9780 -1.6897 -0.3793 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8867 -0.8630 -0.8027 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8020 -1.7663 -0.5393 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3284 0.1787 -1.2723 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8723 0.3558 -1.4476 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2297 0.2152 -0.1747 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3551 1.3625 0.7911 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5460 0.9539 2.0152 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1298 -0.4759 1.9480 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5629 -0.9568 0.6646 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7671 0.1056 -0.3128 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6959 -1.3081 0.7535 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1384 -2.3247 -0.0613 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6013 -3.7011 0.4723 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6580 -4.6254 0.8978 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9721 -4.5877 0.2007 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2701 -5.8893 -0.5380 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2138 -6.9132 0.4063 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0366 -3.5857 -0.7417 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5897 -2.4088 -0.0908 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4380 -1.2624 -0.2644 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4922 -1.0358 0.5670 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3554 0.0201 0.5163 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1264 0.9711 -0.5003 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0988 0.8154 -1.3661 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9413 1.8194 -2.3212 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9897 1.7101 -3.1399 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8166 2.9019 -2.3540 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8386 2.9702 -1.4427 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8193 4.0562 -1.3961 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7529 5.1792 -2.2185 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7461 6.1305 -2.1160 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8001 6.0370 -1.2489 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8938 4.9114 -0.4035 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8869 3.9837 -0.5353 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7771 6.9807 -1.1471 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9239 2.0017 -0.5761 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2642 -0.2758 -1.2602 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2140 -0.4384 -2.1315 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7313 -1.9815 1.6058 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7819 -1.8426 2.5098 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8551 -4.6139 2.2872 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0689 -4.3318 -0.6018 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1945 -1.2847 2.3645 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3868 1.7330 2.0610 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6428 1.6743 1.1719 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1767 1.5611 2.0079 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5660 1.3864 0.8771 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8767 2.9945 1.2533 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2670 -0.1412 0.7425 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5709 -0.0181 -2.5960 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7812 1.8756 -3.4404 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9745 2.9104 -2.4625 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9743 -2.2179 0.0233 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7734 -2.7397 0.0225 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8240 1.4405 -1.7907 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5100 -0.2627 -2.2832 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5390 -0.7271 0.3296 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8455 2.2420 0.3326 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1447 1.0681 2.9565 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3322 -0.6672 2.7780 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2474 -1.7615 0.2209 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5934 -2.2876 -0.9991 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1618 -3.5543 1.2423 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3063 -5.7277 0.7354 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8311 -4.4411 0.9262 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2557 -5.7698 -1.0150 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5404 -6.0037 -1.3607 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4423 -6.4892 1.2678 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8631 -2.7492 1.0470 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1726 0.1953 1.1701 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6871 3.6951 -3.0925 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9351 5.2850 -2.9194 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7385 7.0629 -2.7357 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7071 4.8478 0.2819 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9154 3.0853 0.1175 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4072 7.0500 -0.3377 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4220 0.2172 -2.1999 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7220 -0.9486 3.1687 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8013 -2.7224 3.2300 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7743 -1.7823 1.9950 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2404 -4.0194 2.7391 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7791 -4.9315 -0.2372 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1392 -1.4375 3.3565 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6610 2.6609 2.2244 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5736 2.4548 1.8231 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 5 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 43 46 1 0 39 47 1 0 35 48 2 0 48 49 1 0 32 50 1 0 50 51 1 0 25 52 1 0 24 53 1 0 19 54 1 0 18 55 1 0 17 56 1 0 8 3 1 0 21 16 1 0 30 23 1 0 48 31 1 0 47 34 1 0 45 40 1 0 1 57 1 0 1 58 1 0 1 59 1 0 4 60 1 0 6 61 1 0 7 62 1 0 9 63 1 0 10 64 1 0 11 65 1 0 15 66 1 0 15 67 1 0 16 68 1 1 17 69 1 6 18 70 1 1 19 71 1 1 20 72 1 6 23 73 1 6 24 74 1 1 25 75 1 1 26 76 1 1 27 77 1 0 27 78 1 0 28 79 1 0 30 80 1 1 33 81 1 0 38 82 1 0 41 83 1 0 42 84 1 0 44 85 1 0 45 86 1 0 46 87 1 0 49 88 1 0 51 89 1 0 51 90 1 0 51 91 1 0 52 92 1 0 53 93 1 0 54 94 1 0 55 95 1 0 56 96 1 0 M END

Standard InCHIKey	WZAXZHIVHPRTIU-DKULBZLCSA-N
Standard InCHI	InChI=1S/C38H40O18/c1-50-22-11-16(3-9-19(22)41)4-10-27(43)52-15-26-31(45)33(47)35(49)38(55-26)56-37-34(48)30(44)25(14-39)54-36(37)29-23(51-2)13-24-28(32(29)46)20(42)12-21(53-24)17-5-7-18(40)8-6-17/h3-13,25-26,30-31,33-41,44-49H,14-15H2,1-2H3/b10-4-/t25-,26-,30-,31-,33+,34+,35-,36+,37-,38+/m1/s1
SMILES	COc1cc(ccc1O)/C=CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1c1c(cc2c(c(=O)cc(c3ccc(cc3)O)o2)c1O)OC)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	784.22	Volume:	738.415 ? Van der Waals volume.
Dense:	1.062	LogP:	1.042 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.432 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.438 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	38.0
TPSA:	284.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	9.0	Rings:	6.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.073	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.059	Fsp³:	0.368
MCE-18:	138.769 ? 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:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.692	Fluc inhibitor:	0.607 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.9 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.683 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.056	Promiscuous compounds:	0.301

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.407	MDCK Permeability:	-5.335
Pgp-inhibitor:	0.002	Pgp-substrate:	0.01
PAMPA:	0.987 ? 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):	0.854
20% Bioavailability (F20%):	0.704	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.028
Plasma Protein Binding (PPB):	87.769%	Volume Distribution (VD):	-0.095
Fu:	9.872% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.353
BSEP inhibitor:	0.571

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.011	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.01	CYP2D6-substrate:	0.419
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.978
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.179 ? 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):

1.983

Half-life (T1/2):

3.594

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.235
Human Hepatotoxicity (H-HT):	0.378	Drug-induced Liver Injury (DILI):	0.69
AMES Toxicity:	0.65	Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.096	Skin Sensitization:	1.0
Carcinogencity:	0.011	Eye Corrosion:	0.0
Eye Irritation:	0.325	Respiratory Toxicity:	0.016
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.638
Hematotoxicity:	0.007	Drug-induced Nephrotoxicity:	0.567
Genotoxicity:	0.464	RPMI-8226 Immunitoxicity:	0.28
A549 Cytotoxicity:	0.951	Hek293 Cytotoxicity:	0.871
BCF:	0.57 ? 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:	3.353 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.826 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.127 ? 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
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	small food enterprises (Zvijezda d.d., Zagreb, Croatia)	n.a.	DOI[10.1002/EJLT.200900231]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16660462]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	flower petals	n.a.	n.a.	PMID[17480100]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO5986.2	Ziziphus jujuba var. spinosa	Varieties	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25767684]
NPO5986.2	Ziziphus jujuba var. spinosa	Varieties	Rhamnaceae	Eukaryota	n.a.	seed	n.a.	PMID[26281588]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27617953]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28257196]
NPO5986.2	Ziziphus jujuba var. spinosa	Varieties	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39147551]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[6361218]
NPO5986.2	Ziziphus jujuba var. spinosa	Varieties	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO160	Cynanchum thesioides	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flower Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Pollen Or Spore	n.a.	n.a.	Database[FooDB]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO160	Cynanchum thesioides	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5986.2	Ziziphus jujuba var. spinosa	Varieties	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO160	Cynanchum thesioides	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5986.2	Ziziphus jujuba var. spinosa	Varieties	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO160	Cynanchum thesioides	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO160	Cynanchum thesioides	Species	Apocynaceae	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 NPC268129 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	19473
0.1-0.2	25575
0.2-0.3	3716
0.3-0.4	866
0.4-0.5	196
0.5-0.6	24
0.6-0.7	6
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
0.6909	Remote Similarity	NPC472993
0.6355	Remote Similarity	NPC257566
0.6126	Remote Similarity	NPC270675
0.6126	Remote Similarity	NPC195685
0.6098	Remote Similarity	NPC25946
0.6034	Remote Similarity	NPC480796
0.5826	Remote Similarity	NPC472994
0.5794	Remote Similarity	NPC21359
0.5794	Remote Similarity	NPC460984
0.5714	Remote Similarity	NPC199172
0.5678	Remote Similarity	NPC470416
0.5645	Remote Similarity	NPC488079
0.552	Remote Similarity	NPC488078
0.5517	Remote Similarity	NPC477629
0.5472	Remote Similarity	NPC10807
0.5472	Remote Similarity	NPC161881
0.5385	Remote Similarity	NPC80068
0.531	Remote Similarity	NPC300262
0.531	Remote Similarity	NPC604854
0.5308	Remote Similarity	NPC35924
0.5304	Remote Similarity	NPC606547
0.521	Remote Similarity	NPC36138
0.5207	Remote Similarity	NPC599948
0.5203	Remote Similarity	NPC217520
0.5182	Remote Similarity	NPC226005
0.5182	Remote Similarity	NPC476869
0.5179	Remote Similarity	NPC172807
0.5169	Remote Similarity	NPC479644
0.5133	Remote Similarity	NPC83743
0.5078	Remote Similarity	NPC471030

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC268129 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4697
0.1-0.2	4375
0.2-0.3	69
0.3-0.4	7
0.4-0.5	2
0.5-0.6	0
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
		NPD

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