NPASS Compound

Natural Product: NPC806

Natural Product ID	NPC806
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FUETYOGYMBALQW-ORCPWHRNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	24827807
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0003003] Hydroxycinnamic acid 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 88 91 0 0 0 0 0 0 0 0999 V2000 -6.3388 2.9821 -4.2366 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3937 3.9401 -3.2149 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9827 3.6256 -1.9445 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5098 2.3502 -1.6832 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0927 2.0125 -0.4159 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5996 0.6862 -0.1581 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4691 -0.2989 -1.0143 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9409 -1.6124 -0.5793 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8129 -2.5550 -1.4033 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5626 -1.8971 0.7105 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0629 -3.1389 1.1302 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9333 -3.8535 2.1221 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3919 -5.2642 2.2586 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8926 -5.1835 2.4182 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1647 -5.8635 1.2757 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1934 -6.0243 1.5705 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4122 -3.9335 2.7084 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6946 -2.9640 1.7350 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7136 -2.9093 0.7642 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0287 -1.7314 0.8219 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0694 -1.7850 -0.2767 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7891 -3.0982 -0.2841 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9450 -3.1451 0.6808 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4073 -1.7661 1.0838 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1977 -0.8720 -0.1382 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8502 -0.6667 -0.2758 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8939 0.3482 0.0028 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8981 0.7299 -0.8669 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1854 -0.0472 -1.8101 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6408 1.9942 -0.7392 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5862 2.3372 -1.5706 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3463 3.5529 -1.4986 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1655 4.5052 -0.5385 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9172 5.6790 -0.4869 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8675 5.8627 -1.4453 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0964 4.9436 -2.4350 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3346 3.8097 -2.4439 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0556 5.1304 -3.4007 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6498 7.0330 -1.4313 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7532 -1.7635 1.4612 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6469 -3.8950 1.8035 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1778 -3.4774 -1.5844 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0072 -5.9029 3.3386 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2071 -3.9765 1.5650 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1436 2.9580 0.6209 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6110 4.2208 0.3671 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0225 4.5428 -0.8989 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5012 5.8057 -1.1997 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6480 5.1306 1.4151 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2394 4.8516 2.7171 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9116 3.3871 -5.1183 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8544 2.0373 -3.9177 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3247 2.7504 -4.5945 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4723 1.6259 -2.4871 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2898 0.4512 0.8725 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7527 -0.1263 -2.0302 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0383 -3.7821 0.2275 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9384 -3.4115 3.1162 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6835 -5.8371 1.3519 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6538 -5.8221 3.3226 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2064 -5.3021 0.3287 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5775 -6.8786 1.1150 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3743 -6.0604 2.5247 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6187 -1.9894 2.3068 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7042 -0.9036 0.5924 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4286 -1.5135 1.8121 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4677 -1.7459 -1.2360 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0644 -3.8751 0.0421 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7959 -3.6410 0.1683 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8170 -1.3527 1.9255 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5745 -1.4200 -1.0020 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3744 2.6314 0.0689 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7901 1.6161 -2.3754 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4043 4.3706 0.2400 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7118 6.3964 0.3149 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4938 3.0693 -3.2109 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0365 4.9542 -3.2069 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9094 7.4579 -0.5439 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9594 -2.6989 1.7232 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4451 -4.2782 2.2301 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1293 -3.7454 -1.6189 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4335 -6.7628 3.0761 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1959 -4.0984 0.6035 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8063 2.6406 1.5932 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3205 6.1341 -0.6755 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0024 5.7719 3.2925 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3050 4.2301 2.7628 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0347 4.3136 3.2731 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 1 0 6 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 14 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 36 38 1 0 35 39 1 0 24 40 1 0 23 41 1 0 22 42 1 0 13 43 1 0 12 44 1 0 5 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 46 49 1 0 49 50 1 0 47 3 1 0 18 11 1 0 26 21 1 0 37 32 1 0 1 51 1 0 1 52 1 0 1 53 1 0 4 54 1 0 6 55 1 0 7 56 1 0 11 57 1 6 12 58 1 1 13 59 1 6 14 60 1 1 15 61 1 0 15 62 1 0 16 63 1 0 18 64 1 1 20 65 1 0 20 66 1 0 21 67 1 6 22 68 1 1 23 69 1 6 24 70 1 1 25 71 1 6 30 72 1 0 31 73 1 0 33 74 1 0 34 75 1 0 37 76 1 0 38 77 1 0 39 78 1 0 40 79 1 0 41 80 1 0 42 81 1 0 43 82 1 0 44 83 1 0 45 84 1 0 48 85 1 0 50 86 1 0 50 87 1 0 50 88 1 0 M END

Standard InCHIKey	FUETYOGYMBALQW-ORCPWHRNSA-N
Standard InCHI	InChI=1S/C32H38O18/c1-44-18-10-15(11-19(45-2)24(18)38)5-8-22(36)49-30-28(42)25(39)20(12-33)47-32(30)46-13-21-26(40)27(41)29(43)31(48-21)50-23(37)7-4-14-3-6-16(34)17(35)9-14/h3-11,20-21,25-35,38-43H,12-13H2,1-2H3/b7-4+,8-5+/t20-,21-,25-,26-,27+,28+,29-,30-,31+,32-/m1/s1
SMILES	COc1cc(/C=C/C(=O)O[C@@H]2[C@H]([C@@H]([C@@H](CO)O[C@H]2OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC(=O)/C=C/c2ccc(c(c2)O)O)O)O)O)O)O)cc(c1O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	710.21	Volume:	659.662 ? Van der Waals volume.
Dense:	1.077	LogP:	-0.201 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.515 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.521 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	28.0
TPSA:	280.82 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	9.0	Rings:	4.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.067	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.895	Fsp³:	0.438
MCE-18:	106.478 ? 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:	1
Colloidal aggregators:	0.753	Fluc inhibitor:	0.687 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.145 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.642 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.205	Promiscuous compounds:	0.435

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.32	MDCK Permeability:	-5.425
Pgp-inhibitor:	0.0	Pgp-substrate:	0.087
PAMPA:	0.989 ? 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):	0.997
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.018
Plasma Protein Binding (PPB):	74.49%	Volume Distribution (VD):	-0.229
Fu:	23.663% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.06
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:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.155 ? 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):

1.279

Half-life (T1/2):

3.168

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.175
Human Hepatotoxicity (H-HT):	0.576	Drug-induced Liver Injury (DILI):	0.901
AMES Toxicity:	0.931	Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.037	Skin Sensitization:	1.0
Carcinogencity:	0.046	Eye Corrosion:	0.0
Eye Irritation:	0.06	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.985
Hematotoxicity:	0.091	Drug-induced Nephrotoxicity:	0.754
Genotoxicity:	0.267	RPMI-8226 Immunitoxicity:	0.104
A549 Cytotoxicity:	0.939	Hek293 Cytotoxicity:	0.415
BCF:	0.585 ? 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:	3.376 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.096 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.423 ? 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
NPO28141	Colpomenia sinuosa	Species	Scytosiphonaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np50097a033]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12802735]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[18384095]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[22014120]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014120]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014168]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23540838]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295708]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[25102361]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[25306330]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35986990]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36770740]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36985747]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37087263]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37924762]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38306771]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38474614]
NPO27905	Eritrichium sericeum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21557	Woodsia manchuriensis	Species	Woodsiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28556	Streptomyces pentaticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28646	Streptomyces argenteolus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28422	Sabia japonica	Species	Sabiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28195	Phlogacanthus tubiflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20714	Lobophytum schoedei	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28263	Anemone tomentosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28141	Colpomenia sinuosa	Species	Scytosiphonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28070	Chrysosplenium americanum	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23326	Bohadschia vitiensis	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27829	Aplophyllum pedicellatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28070	Chrysosplenium americanum	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21557	Woodsia manchuriensis	Species	Woodsiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20714	Lobophytum schoedei	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23326	Bohadschia vitiensis	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28422	Sabia japonica	Species	Sabiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28646	Streptomyces argenteolus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28195	Phlogacanthus tubiflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28141	Colpomenia sinuosa	Species	Scytosiphonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27829	Aplophyllum pedicellatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27905	Eritrichium sericeum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28556	Streptomyces pentaticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28263	Anemone tomentosa	Species	Ranunculaceae	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 NPC806 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	16315
0.1-0.2	27317
0.2-0.3	5022
0.3-0.4	952
0.4-0.5	208
0.5-0.6	36
0.6-0.7	5
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
0.6322	Remote Similarity	NPC476868
0.6164	Remote Similarity	NPC232880
0.6104	Remote Similarity	NPC157554
0.6092	Remote Similarity	NPC476864
0.6	Remote Similarity	NPC476865
0.5977	Remote Similarity	NPC476867
0.5976	Remote Similarity	NPC473924
0.5955	Remote Similarity	NPC90896
0.5943	Remote Similarity	NPC484984
0.573	Remote Similarity	NPC472612
0.5638	Remote Similarity	NPC283839
0.5591	Remote Similarity	NPC83743
0.5581	Remote Similarity	NPC297342
0.5567	Remote Similarity	NPC472611
0.5566	Remote Similarity	NPC484982
0.5556	Remote Similarity	NPC484983
0.5495	Remote Similarity	NPC476869
0.5495	Remote Similarity	NPC476866
0.5484	Remote Similarity	NPC289967
0.5476	Remote Similarity	NPC477294
0.5385	Remote Similarity	NPC246869
0.5385	Remote Similarity	NPC225384
0.5364	Remote Similarity	NPC484981
0.5361	Remote Similarity	NPC173343
0.5341	Remote Similarity	NPC219677
0.5326	Remote Similarity	NPC226005
0.5319	Remote Similarity	NPC262182
0.5294	Remote Similarity	NPC229784
0.5238	Remote Similarity	NPC470572
0.5217	Remote Similarity	NPC157816
0.5208	Remote Similarity	NPC216819
0.5195	Remote Similarity	NPC11724
0.519	Remote Similarity	NPC132895
0.5181	Remote Similarity	NPC202700
0.5155	Remote Similarity	NPC300262
0.5116	Remote Similarity	NPC477293
0.5059	Remote Similarity	NPC163883
0.5057	Remote Similarity	NPC287597
0.5051	Remote Similarity	NPC125823
0.5051	Remote Similarity	NPC7145
0.5051	Remote Similarity	NPC143480

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC806 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5054
0.1-0.2	3995
0.2-0.3	96
0.3-0.4	3
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