NPASS Compound

Natural Product: NPC103209

Natural Product ID	NPC103209
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FHXACOPOJBXRQQ-BANNQNFNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11968791
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 94 99 0 0 0 0 0 0 0 0999 V2000 -4.8870 0.4086 -3.7163 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3802 0.1426 -2.2867 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8673 0.1653 -2.3348 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4834 -1.1820 -2.5462 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8107 -2.1837 -1.6599 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6769 -1.5750 -0.8590 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8125 -1.0221 -1.7924 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0565 -0.6105 0.0291 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7081 -0.8163 1.3443 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9951 -0.8315 2.1367 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6534 -1.0689 3.5884 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4555 -0.2495 4.0123 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2931 -1.1536 4.3677 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2504 -0.4398 4.9516 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1302 0.7339 3.1335 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9012 0.3682 1.8189 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5350 0.1654 1.6487 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6472 0.8913 0.8990 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0613 1.9807 0.1841 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1159 2.6766 -0.5560 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7995 2.2869 -0.5741 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1487 3.0643 -1.3755 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1964 4.1318 -1.9305 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5269 2.5490 -1.5095 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9245 1.8125 -0.2449 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3036 1.3225 -0.3280 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6489 0.1424 -0.9502 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9439 -0.3082 -1.0242 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0055 0.4205 -0.4607 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6572 1.6009 0.1614 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3399 2.0398 0.2255 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2676 -0.0854 -0.5705 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4293 0.4689 -0.0891 C 0 0 2 0 0 0 0 0 0 0 0 0 9.4151 0.7903 -1.1967 C 0 0 1 0 0 0 0 0 0 0 0 0 10.1571 -0.4062 -1.6919 C 0 0 2 0 0 0 0 0 0 0 0 0 10.4647 -1.4134 -0.6236 C 0 0 2 0 0 0 0 0 0 0 0 0 9.2528 -1.5899 0.2639 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4882 -2.6809 1.2860 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7190 -3.8772 0.6271 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0156 -0.3592 0.8741 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5839 -1.0223 0.1097 O 0 0 0 0 0 0 0 0 0 0 0 0 11.3914 0.0453 -2.2061 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6484 1.2773 -2.2765 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9908 0.8100 0.1085 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3486 1.1863 0.1410 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2923 0.5109 0.8652 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5311 3.7812 -1.2814 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7544 -0.8249 4.4027 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9369 -1.6980 1.6499 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1918 -3.1176 -2.5271 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3653 -1.4803 -3.9066 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2962 0.9890 -3.4032 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8101 0.1562 -3.8175 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5249 -0.1244 -4.4446 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0238 1.4884 -3.9029 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0346 1.0365 -1.6983 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3484 0.6363 -1.4353 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5672 -1.0970 -2.3056 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5320 -2.7354 -1.0573 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1188 -2.3844 -0.3313 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1517 -1.7711 1.4374 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4055 0.2110 2.0721 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3836 -2.1365 3.6996 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7455 0.2499 4.9644 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6007 -1.9066 5.1515 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9521 -1.7688 3.5111 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5112 -1.0568 5.1269 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2419 1.2285 1.2083 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0823 2.3531 0.1464 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2492 3.3905 -1.6153 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6737 1.8931 -2.3943 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8565 2.5854 0.5730 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8444 -0.4507 -1.4004 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2100 -1.2358 -1.5144 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4390 2.2095 0.6160 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1032 2.9729 0.7221 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2337 1.4246 0.4255 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0875 1.6154 -0.8940 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6420 -0.8885 -2.5722 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7008 -2.3737 -1.1193 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4059 -1.8759 -0.3627 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5489 -2.7883 1.8717 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3475 -2.4496 1.9536 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4666 -3.8294 -0.3145 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3489 -0.1896 0.5942 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6656 0.7998 -1.6353 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0891 2.0551 -2.6960 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0179 -0.3474 1.4399 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2801 4.6926 -0.8879 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5186 -0.7059 5.3418 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7434 -1.2174 1.2836 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8086 -3.8146 -2.8113 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1860 -1.9643 -4.1697 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2129 1.3474 -3.2233 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 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 29 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 37 40 1 0 36 41 1 0 35 42 1 0 34 43 1 0 25 44 1 0 44 45 1 0 45 46 2 0 20 47 1 0 11 48 1 0 10 49 1 0 5 50 1 0 4 51 1 0 3 52 1 0 7 2 1 0 16 9 1 0 46 18 1 0 45 21 1 0 31 26 1 0 40 33 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 1 3 57 1 1 4 58 1 1 5 59 1 1 6 60 1 1 9 61 1 6 10 62 1 1 11 63 1 6 12 64 1 1 13 65 1 0 13 66 1 0 14 67 1 0 16 68 1 6 19 69 1 0 24 70 1 0 24 71 1 0 25 72 1 0 27 73 1 0 28 74 1 0 30 75 1 0 31 76 1 0 33 77 1 1 34 78 1 1 35 79 1 6 36 80 1 6 37 81 1 6 38 82 1 0 38 83 1 0 39 84 1 0 41 85 1 0 42 86 1 0 43 87 1 0 46 88 1 0 47 89 1 0 48 90 1 0 49 91 1 0 50 92 1 0 51 93 1 0 52 94 1 0 M END

Standard InCHIKey	FHXACOPOJBXRQQ-BANNQNFNSA-N
Standard InCHI	InChI=1S/C33H42O19/c1-11-22(38)25(41)28(44)31(46-11)52-30-27(43)24(40)20(10-35)51-33(30)48-14-6-15(36)21-16(37)8-17(49-18(21)7-14)12-2-4-13(5-3-12)47-32-29(45)26(42)23(39)19(9-34)50-32/h2-7,11,17,19-20,22-36,38-45H,8-10H2,1H3/t11-,17?,19+,20+,22+,23-,24+,25+,26-,27-,28+,29+,30+,31-,32-,33+/m0/s1
SMILES	C[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]1Oc1cc(c2C(=O)CC(c3ccc(cc3)O[C@@H]3[C@@H]([C@H]([C@H]([C@@H](CO)O3)O)O)O)Oc2c1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	742.23	Volume:	676.544 ? Van der Waals volume.
Dense:	1.097	LogP:	-0.639 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.195 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.786 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	36.0
TPSA:	304.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.118	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.324	Fsp³:	0.606
MCE-18:	149.302 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.629	Fluc inhibitor:	0.351 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.122 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.368 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.311	Promiscuous compounds:	0.304

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.059	MDCK Permeability:	-4.895
Pgp-inhibitor:	0.0	Pgp-substrate:	0.626
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):	1.0
20% Bioavailability (F20%):	0.861	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.143
Plasma Protein Binding (PPB):	79.61%	Volume Distribution (VD):	-0.34
Fu:	19.671% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.009
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.037 ? 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):

0.536

Half-life (T1/2):

4.258

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.033
Human Hepatotoxicity (H-HT):	0.905	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.997	Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.004	Skin Sensitization:	1.0
Carcinogencity:	0.097	Eye Corrosion:	0.0
Eye Irritation:	0.011	Respiratory Toxicity:	0.018
Drug-induced Neurotoxicity:	0.018	Ototoxicity:	0.999
Hematotoxicity:	0.852	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	0.967	RPMI-8226 Immunitoxicity:	0.542
A549 Cytotoxicity:	0.994	Hek293 Cytotoxicity:	0.803
BCF:	0.401 ? 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:	3.133 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.991 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.024 ? 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
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11599360]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	flowers	n.a.	n.a.	PMID[12193020]
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2045817]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381697]
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	seeds	n.a.	n.a.	PMID[23985009]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24485782]
NPO21356	Helichrysum arenarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35209096]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37049761]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37120447]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[7092570]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[8021657]
NPO8258.1	Camellia sinensis var. assamica	Varieties	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21356	Helichrysum arenarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO4739	Prunus yedoensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21356	Helichrysum arenarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8258.1	Camellia sinensis var. assamica	Varieties	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21356	Helichrysum arenarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4739	Prunus yedoensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8258.1	Camellia sinensis var. assamica	Varieties	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4739	Prunus yedoensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21356	Helichrysum arenarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4739	Prunus yedoensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	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 NPC103209 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	16639
0.1-0.2	28151
0.2-0.3	4266
0.3-0.4	687
0.4-0.5	79
0.5-0.6	15
0.6-0.7	9
0.7-0.8	0
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8861	High Similarity	NPC97285
0.8395	Intermediate Similarity	NPC142860
0.8395	Intermediate Similarity	NPC152538
0.8395	Intermediate Similarity	NPC246469
0.8395	Intermediate Similarity	NPC89088
0.8095	Intermediate Similarity	NPC105095
0.8095	Intermediate Similarity	NPC177731
0.8095	Intermediate Similarity	NPC725
0.7976	Intermediate Similarity	NPC291124
0.7976	Intermediate Similarity	NPC131157
0.75	Intermediate Similarity	NPC105283
0.7342	Intermediate Similarity	NPC219163
0.7	Intermediate Similarity	NPC97052
0.6914	Remote Similarity	NPC39351
0.6548	Remote Similarity	NPC29830
0.6506	Remote Similarity	NPC26195
0.6322	Remote Similarity	NPC236934
0.6264	Remote Similarity	NPC271270
0.6064	Remote Similarity	NPC44328
0.6064	Remote Similarity	NPC79056
0.6	Remote Similarity	NPC170475
0.6	Remote Similarity	NPC293629
0.5957	Remote Similarity	NPC43587
0.5955	Remote Similarity	NPC479540
0.5816	Remote Similarity	NPC261254
0.5534	Remote Similarity	NPC241196
0.5417	Remote Similarity	NPC200708
0.5417	Remote Similarity	NPC604887
0.54	Remote Similarity	NPC47140
0.5333	Remote Similarity	NPC206378
0.5185	Remote Similarity	NPC23084
0.5182	Remote Similarity	NPC469371
0.5169	Remote Similarity	NPC169248
0.5169	Remote Similarity	NPC72649
0.5111	Remote Similarity	NPC163191
0.506	Remote Similarity	NPC607702
0.5054	Remote Similarity	NPC5778

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC103209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4558
0.1-0.2	4471
0.2-0.3	111
0.3-0.4	9
0.4-0.5	0
0.5-0.6	0
0.6-0.7	1
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
0.6064	Remote Similarity	NPD7074	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