NPASS Compound

Natural Product: NPC280642

Natural Product ID	NPC280642
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Kaempferol 3-O-(3' ',6' '-Di-O-E-P-Coumaroyl)-Beta-D-Glucopyranoside
IUPAC Name	[(2R,3R,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,5-dihydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL446770
PubChem CID	10032927
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003678] Flavonoid 3-O-p-coumaroyl 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 86 91 0 0 0 0 0 0 0 0999 V2000 7.7537 -0.4057 0.2025 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9754 -0.3117 0.8231 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2137 -0.9935 2.0006 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1951 -1.7560 2.5155 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9704 -1.8493 1.8925 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7289 -1.1725 0.7204 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4577 -1.2230 0.0037 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4050 -1.9036 0.3794 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1460 -1.9241 -0.3752 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1746 -2.6011 0.0474 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9703 -1.2268 -1.5450 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8432 -1.1642 -2.3377 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6044 -0.6077 -1.7384 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7581 0.8501 -1.3246 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6516 1.3717 -1.1751 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5610 0.4850 -0.3735 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2634 -0.9811 -0.5412 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0869 -1.2533 -0.6585 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7707 -1.6681 0.6314 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0196 -2.2623 0.6492 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0578 -1.4836 1.1483 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8919 -0.3045 1.5891 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3246 -2.0322 1.1648 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3907 -1.3021 1.6469 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6434 -1.8659 1.6534 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8171 -3.1454 1.1812 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7515 -3.8594 0.7056 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4668 -3.3108 0.6874 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4570 -4.0049 0.2305 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1969 -3.5331 0.1864 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1671 -4.4135 -0.3443 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5578 -5.5199 -1.1177 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6267 -6.4176 -1.5887 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2765 -6.2817 -1.3303 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1143 -5.2022 -0.5732 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8342 -4.3058 -0.1045 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6186 -7.2156 -1.8308 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1068 -3.6827 1.2047 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1484 -0.0030 2.1143 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8411 0.6840 -0.9643 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5959 2.6847 -0.7448 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9867 3.7590 -1.5273 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4003 3.4724 -2.6679 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9317 5.1548 -1.0762 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5001 5.4527 0.1121 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4340 6.8155 0.5856 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8196 7.8746 -0.1730 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7196 9.1602 0.3713 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2517 9.4019 1.6320 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1304 8.3191 2.3764 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0497 7.0494 1.8852 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1763 10.7121 2.1187 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4005 1.6015 -2.2973 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4267 -0.9319 2.6640 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6251 0.1585 -0.7296 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8033 0.2881 0.4347 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3778 -2.3020 3.4536 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1927 -2.4517 2.3164 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3418 -0.6582 -0.9250 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4568 -2.4799 1.2868 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5761 -2.1245 -2.8316 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0996 -0.4871 -3.2078 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1796 -0.6072 -2.5399 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2383 0.9105 -0.3342 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0566 1.3875 -2.2327 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5487 0.7004 0.6983 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8557 -1.3179 -1.4362 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4827 -1.2748 2.0398 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8759 -4.8646 0.3317 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6164 -5.6109 -1.3107 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9615 -7.2627 -2.1844 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1723 -5.1102 -0.3790 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4698 -3.5070 0.5166 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0241 -7.9500 -1.2771 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7504 -3.4138 0.4679 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7011 0.3429 2.8999 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7658 0.3004 -1.8672 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2571 5.9066 -1.7572 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1731 4.6332 0.7813 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2040 7.7585 -1.1894 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0411 9.9679 -0.2769 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5047 8.4974 3.3813 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3539 6.1740 2.4749 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7594 11.4126 1.6769 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3602 1.7439 -2.1010 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1871 -1.4889 2.2906 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 9 10 2 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 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 2 0 34 37 1 0 26 38 1 0 24 39 1 0 16 40 1 0 15 41 1 0 41 42 1 0 42 43 2 0 42 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 49 52 1 0 14 53 1 0 3 54 1 0 6 1 1 0 18 13 1 0 30 20 2 0 36 31 1 0 51 46 1 0 28 23 1 0 1 55 1 0 2 56 1 0 4 57 1 0 5 58 1 0 7 59 1 0 8 60 1 0 12 61 1 0 12 62 1 0 13 63 1 6 14 64 1 1 15 65 1 6 16 66 1 1 17 67 1 6 25 68 1 0 27 69 1 0 32 70 1 0 33 71 1 0 35 72 1 0 36 73 1 0 37 74 1 0 38 75 1 0 39 76 1 0 40 77 1 0 44 78 1 0 45 79 1 0 47 80 1 0 48 81 1 0 50 82 1 0 51 83 1 0 52 84 1 0 53 85 1 0 54 86 1 0 M END

Standard InCHIKey	NFSCOXCDAAETPI-WSLAOOLZSA-N
Standard InCHI	InChI=1S/C39H32O15/c40-23-9-1-20(2-10-23)5-15-30(45)50-19-29-33(47)37(53-31(46)16-6-21-3-11-24(41)12-4-21)35(49)39(52-29)54-38-34(48)32-27(44)17-26(43)18-28(32)51-36(38)22-7-13-25(42)14-8-22/h1-18,29,33,35,37,39-44,47,49H,19H2/b15-5+,16-6+/t29-,33-,35-,37+,39+/m1/s1
SMILES	c1cc(ccc1/C=C/C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(cc1)O)O)O)O)OC(=O)/C=C/c1ccc(cc1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	740.17	Volume:	716.158 ? Van der Waals volume.
Dense:	1.034	LogP:	2.728 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.388 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.933 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	40.0
TPSA:	242.88 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	7.0	Rings:	6.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.08	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.516	Fsp³:	0.154
MCE-18:	122.444 ? 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:	0.998	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.884 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.755 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.344	Promiscuous compounds:	0.77

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.661	MDCK Permeability:	-5.064
Pgp-inhibitor:	0.065	Pgp-substrate:	0.014
PAMPA:	0.955 ? 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):	0.0
20% Bioavailability (F20%):	0.954	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	90.456%	Volume Distribution (VD):	0.143
Fu:	11.38% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.393
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.871
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.004	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.807 ? 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):

2.373

Half-life (T1/2):

2.993

ADMET: Toxicity

hERG Blockers:	0.085	hERG Blockers (10um):	0.552
Human Hepatotoxicity (H-HT):	0.577	Drug-induced Liver Injury (DILI):	0.953
AMES Toxicity:	0.8	Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.939	Skin Sensitization:	1.0
Carcinogencity:	0.186	Eye Corrosion:	0.0
Eye Irritation:	0.799	Respiratory Toxicity:	0.068
Drug-induced Neurotoxicity:	0.095	Ototoxicity:	0.261
Hematotoxicity:	0.006	Drug-induced Nephrotoxicity:	0.175
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.134
A549 Cytotoxicity:	0.906	Hek293 Cytotoxicity:	0.993
BCF:	0.82 ? 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:	4.091 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.885 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.723 ? 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
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1023/A:1025674116183]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1324982]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[13465274]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1536925]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180822]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17512094]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19376614]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	seed	n.a.	PMID[24225786]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3509958]
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39073007]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO12512	Stenochlaena palustris	Species	Blechnaceae	Eukaryota	leaves	n.a.	n.a.	PMID[9917285]
NPO5975	Aspergillus carneus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18993	Araiostegiella perdurans	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3554	Aonidiella aurantii	Species	Diaspididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5584	Aldisa sanguinea	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4274	Alcyonium utinomii	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25760	Aspergillus striatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3408	Viguiera decurrens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5261	Sideroxylon cubense	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3743	Sideritis brevibracteata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4949	Salvia yosgadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7606	Salacia lehmbachii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1489	Pseudoplexaura flagellosa	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8058	Pluchea odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2993	Nototodarus sloanii	Species	Ommastrephidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12512	Stenochlaena palustris	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1390	Melolontha melolontha	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3956	Maesa ramentacea	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7760	Macrolepiota neomastoidea	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO295	Kokoona reflexa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2250	Hylocomium splendens	Species	Hylocomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15487	Gymnopus confluens	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO849	Euonymus tingens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7007	Eucalyptus jenseni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7449	Eleutherobia albiflora	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6231	Cortinarius odoratus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1242	Balanops australiana	Species	Balanopaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18993	Araiostegiella perdurans	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5975	Aspergillus carneus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO295	Kokoona reflexa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2250	Hylocomium splendens	Species	Hylocomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5261	Sideroxylon cubense	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7007	Eucalyptus jenseni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7606	Salacia lehmbachii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3956	Maesa ramentacea	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6231	Cortinarius odoratus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2993	Nototodarus sloanii	Species	Ommastrephidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO849	Euonymus tingens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1242	Balanops australiana	Species	Balanopaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12512	Stenochlaena palustris	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1489	Pseudoplexaura flagellosa	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3408	Viguiera decurrens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4274	Alcyonium utinomii	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7760	Macrolepiota neomastoidea	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3554	Aonidiella aurantii	Species	Diaspididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15487	Gymnopus confluens	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5584	Aldisa sanguinea	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25760	Aspergillus striatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1390	Melolontha melolontha	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8058	Pluchea odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7449	Eleutherobia albiflora	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3743	Sideritis brevibracteata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4949	Salvia yosgadensis	Species	Lamiaceae	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

Activity Type	# Activity
MIC	4

Activity Type	# Activity
Organism	4

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
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	256.0	ug.mL-1	PMID[9917285]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	256.0	ug.mL-1	PMID[9917285]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	256.0	ug.mL-1	PMID[9917285]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	>	256.0	ug.mL-1	PMID[9917285]

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 NPC280642 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	15144
0.1-0.2	30658
0.2-0.3	3255
0.3-0.4	477
0.4-0.5	188
0.5-0.6	85
0.6-0.7	32
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC96605
0.914	High Similarity	NPC474093
0.914	High Similarity	NPC104910
0.8242	Intermediate Similarity	NPC205824
0.7957	Intermediate Similarity	NPC85751
0.7957	Intermediate Similarity	NPC19240
0.767	Intermediate Similarity	NPC241781
0.7658	Intermediate Similarity	NPC475179
0.7604	Intermediate Similarity	NPC218161
0.7423	Intermediate Similarity	NPC223426
0.7347	Intermediate Similarity	NPC214621
0.7347	Intermediate Similarity	NPC34267
0.7188	Intermediate Similarity	NPC104883
0.7188	Intermediate Similarity	NPC488679
0.7129	Intermediate Similarity	NPC477895
0.7059	Intermediate Similarity	NPC217520
0.6832	Remote Similarity	NPC478277
0.6832	Remote Similarity	NPC478276
0.6832	Remote Similarity	NPC478275
0.6832	Remote Similarity	NPC92815
0.6832	Remote Similarity	NPC81042
0.6768	Remote Similarity	NPC101399
0.6768	Remote Similarity	NPC221288
0.6768	Remote Similarity	NPC217822
0.6768	Remote Similarity	NPC11847
0.6768	Remote Similarity	NPC198938
0.6768	Remote Similarity	NPC194836
0.6768	Remote Similarity	NPC91493
0.6768	Remote Similarity	NPC605081
0.6635	Remote Similarity	NPC473278
0.6634	Remote Similarity	NPC36138
0.663	Remote Similarity	NPC129217
0.6465	Remote Similarity	NPC470125
0.6449	Remote Similarity	NPC139571
0.625	Remote Similarity	NPC483767
0.625	Remote Similarity	NPC483769
0.625	Remote Similarity	NPC483768
0.625	Remote Similarity	NPC483766
0.6075	Remote Similarity	NPC470416
0.6071	Remote Similarity	NPC156785
0.6071	Remote Similarity	NPC474522
0.6071	Remote Similarity	NPC471030
0.6058	Remote Similarity	NPC477629
0.604	Remote Similarity	NPC129264
0.6038	Remote Similarity	NPC483765
0.6	Remote Similarity	NPC260504
0.6	Remote Similarity	NPC470716
0.6	Remote Similarity	NPC89809
0.5981	Remote Similarity	NPC203145
0.5963	Remote Similarity	NPC470712
0.5948	Remote Similarity	NPC25946
0.5932	Remote Similarity	NPC231787
0.5929	Remote Similarity	NPC162394
0.5876	Remote Similarity	NPC85707
0.5868	Remote Similarity	NPC249560
0.5833	Remote Similarity	NPC72554
0.5798	Remote Similarity	NPC275977
0.5773	Remote Similarity	NPC159579
0.5714	Remote Similarity	NPC470718
0.57	Remote Similarity	NPC116864
0.57	Remote Similarity	NPC244776
0.5673	Remote Similarity	NPC296018
0.5645	Remote Similarity	NPC97817
0.5625	Remote Similarity	NPC33083
0.5591	Remote Similarity	NPC54802
0.5591	Remote Similarity	NPC197304
0.5588	Remote Similarity	NPC471079
0.5574	Remote Similarity	NPC30011
0.5567	Remote Similarity	NPC52550
0.5566	Remote Similarity	NPC210961
0.5566	Remote Similarity	NPC270448
0.5537	Remote Similarity	NPC473554
0.5534	Remote Similarity	NPC173582
0.5534	Remote Similarity	NPC265885
0.5534	Remote Similarity	NPC181465
0.5534	Remote Similarity	NPC215710
0.5534	Remote Similarity	NPC473438
0.5534	Remote Similarity	NPC253788
0.5532	Remote Similarity	NPC288084
0.5528	Remote Similarity	NPC487502
0.5524	Remote Similarity	NPC153755
0.55	Remote Similarity	NPC21359
0.55	Remote Similarity	NPC460984
0.5495	Remote Similarity	NPC189564
0.5463	Remote Similarity	NPC80068
0.5455	Remote Similarity	NPC48093
0.5417	Remote Similarity	NPC111929
0.5417	Remote Similarity	NPC320283
0.5417	Remote Similarity	NPC41121
0.54	Remote Similarity	NPC259957
0.537	Remote Similarity	NPC270675
0.537	Remote Similarity	NPC195685
0.5361	Remote Similarity	NPC77672
0.5361	Remote Similarity	NPC133671
0.5361	Remote Similarity	NPC135391
0.5361	Remote Similarity	NPC78263
0.5361	Remote Similarity	NPC250069
0.5354	Remote Similarity	NPC216496
0.5299	Remote Similarity	NPC470713
0.5263	Remote Similarity	NPC164704
0.5248	Remote Similarity	NPC224530
0.5238	Remote Similarity	NPC196127
0.5234	Remote Similarity	NPC154741
0.5204	Remote Similarity	NPC104677
0.5185	Remote Similarity	NPC477628
0.5149	Remote Similarity	NPC175107
0.5143	Remote Similarity	NPC609888
0.5138	Remote Similarity	NPC37668
0.5094	Remote Similarity	NPC67326
0.5091	Remote Similarity	NPC603079
0.5089	Remote Similarity	NPC470450
0.5089	Remote Similarity	NPC472994
0.5085	Remote Similarity	NPC488734
0.5085	Remote Similarity	NPC488735
0.5085	Remote Similarity	NPC488739
0.5085	Remote Similarity	NPC488732
0.5085	Remote Similarity	NPC488738
0.5052	Remote Similarity	NPC276222
0.5052	Remote Similarity	NPC274618
0.5052	Remote Similarity	NPC118284
0.5052	Remote Similarity	NPC608147
0.5047	Remote Similarity	NPC203259
0.5047	Remote Similarity	NPC33054
0.5047	Remote Similarity	NPC176740
0.5047	Remote Similarity	NPC471725
0.5047	Remote Similarity	NPC134532
0.5047	Remote Similarity	NPC156869
0.5047	Remote Similarity	NPC602582
0.5046	Remote Similarity	NPC297503
0.5046	Remote Similarity	NPC245452
0.5045	Remote Similarity	NPC471669
0.5043	Remote Similarity	NPC292019
0.5043	Remote Similarity	NPC202908

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC280642 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4240
0.1-0.2	4848
0.2-0.3	55
0.3-0.4	6
0.4-0.5	0
0.5-0.6	1
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
0.5047	Remote Similarity	NPD6797	Phase 2

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