NPASS Compound

Natural Product: NPC162394

Natural Product ID	NPC162394
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Camelliquercetiside D
IUPAC Name	[(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-4,5-dihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms	Camelliquercetiside D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1957049
PubChem CID	57384062
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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 90 95 0 0 0 0 0 0 0 0999 V2000 5.3991 1.3805 3.1297 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2222 1.2918 1.6313 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4840 1.6460 0.8806 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1346 1.7412 -0.5907 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4859 0.4450 -1.0154 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3728 0.0450 -0.0638 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2772 0.8714 -0.1628 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1383 0.1367 -0.5944 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9438 1.0692 -0.6981 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8010 1.7438 0.6323 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0825 0.9055 1.6435 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1707 0.2866 1.0401 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8549 -0.4034 -0.2354 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1605 0.4130 -1.0906 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1117 -1.6067 -0.1219 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5069 -2.7450 -0.8331 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0763 -2.7951 -2.1670 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6165 -1.9021 -2.7018 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4323 -3.8774 -2.9281 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0508 -4.0086 -4.2578 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4083 -5.0954 -5.0277 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1737 -6.0737 -4.4290 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5528 -5.9466 -3.1139 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1982 -4.8530 -2.3226 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5639 -4.7520 -1.0873 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2556 -3.7276 -0.2767 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7480 -3.7778 1.0957 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3142 -3.0030 2.1310 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8591 -3.0756 3.4039 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8858 -3.9565 3.6781 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3373 -4.7481 2.6474 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7782 -4.6563 1.3895 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3665 -5.6360 2.9117 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4332 -4.0282 4.9580 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5229 -7.1592 -5.2204 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7135 -3.0216 -4.8403 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0146 1.4366 0.7730 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1918 1.5896 1.4504 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5510 0.7412 2.3007 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0001 2.7705 1.1434 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6318 3.6648 0.2566 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3908 4.8544 -0.0890 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9209 5.7453 -1.0430 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6212 6.8764 -1.3824 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8323 7.1604 -0.7714 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3201 6.2939 0.1775 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5933 5.1409 0.5147 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4725 8.3247 -1.1749 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9548 -0.0478 2.1383 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1660 2.9932 0.4513 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8641 -0.0067 1.2581 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3900 -0.6181 -1.0573 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2587 1.9258 -1.3924 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0010 2.8583 1.3281 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9858 2.2443 3.4436 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3702 1.4618 3.5747 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8214 0.4283 3.5508 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4388 2.0027 1.3006 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2296 0.8084 0.9838 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3785 2.5365 -0.7140 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0476 0.5382 -2.0239 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0628 -0.9810 -0.3496 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9714 -0.6594 0.1440 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4437 -0.2965 -1.5625 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2632 1.8471 -1.4744 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8057 2.0019 1.0793 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2188 1.5584 2.4923 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6951 -0.2756 1.7987 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8515 -0.6301 -0.7379 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0774 -5.1357 -6.0567 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1570 -6.7260 -2.6555 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5014 -2.3149 1.9891 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5028 -2.4522 4.2161 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1435 -5.2881 0.5778 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4352 -6.4516 2.2991 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4510 -4.1690 4.9970 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5975 -8.0534 -4.7152 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6871 -2.8299 -4.5725 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9283 2.8837 1.6787 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6792 3.4939 -0.2571 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9704 5.4960 -1.5040 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2002 7.5397 -2.1396 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2683 6.5216 0.6518 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0132 4.4958 1.2593 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3915 8.5762 -0.8129 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5728 0.3362 2.7813 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4425 3.3386 -0.4528 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2699 -0.3404 -1.4381 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4777 2.9065 -1.4893 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8100 2.7576 1.8626 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 7 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 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 30 34 1 0 22 35 1 0 20 36 1 0 12 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 45 48 1 0 11 49 1 0 10 50 1 0 6 51 1 0 5 52 1 0 4 53 1 0 3 54 1 0 51 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 47 42 1 0 24 19 1 0 1 55 1 0 1 56 1 0 1 57 1 0 2 58 1 6 3 59 1 6 4 60 1 1 5 61 1 6 6 62 1 6 8 63 1 0 8 64 1 0 9 65 1 6 10 66 1 1 11 67 1 1 12 68 1 1 13 69 1 6 21 70 1 0 23 71 1 0 28 72 1 0 29 73 1 0 32 74 1 0 33 75 1 0 34 76 1 0 35 77 1 0 36 78 1 0 40 79 1 0 41 80 1 0 43 81 1 0 44 82 1 0 46 83 1 0 47 84 1 0 48 85 1 0 49 86 1 0 50 87 1 0 52 88 1 0 53 89 1 0 54 90 1 0 M END

Standard InCHIKey	IJYHCBQZOMHTFY-WAUDLAJOSA-N
Standard InCHI	InChI=1S/C36H36O18/c1-14-26(43)29(46)31(48)35(50-14)49-13-23-27(44)30(47)34(53-24(42)9-4-15-2-6-17(37)7-3-15)36(52-23)54-33-28(45)25-21(41)11-18(38)12-22(25)51-32(33)16-5-8-19(39)20(40)10-16/h2-12,14,23,26-27,29-31,34-41,43-44,46-48H,13H2,1H3/b9-4+/t14-,23+,26-,27+,29+,30-,31+,34+,35+,36-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)Oc2c(=O)c3c(cc(cc3oc2c2ccc(c(c2)O)O)O)O)OC(=O)/C=C/c2ccc(cc2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	756.19	Volume:	703.823 ? Van der Waals volume.
Dense:	1.074	LogP:	1.324 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.435 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.865 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	38.0
TPSA:	295.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	10.0	Rings:	6.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.062	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.08	Fsp³:	0.333
MCE-18:	140.083 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.716	Fluc inhibitor:	0.576 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.82 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.671 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.284	Promiscuous compounds:	0.574

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.451	MDCK Permeability:	-5.13
Pgp-inhibitor:	0.0	Pgp-substrate:	0.07
PAMPA:	0.998 ? 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):	0.393
20% Bioavailability (F20%):	0.975	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.001
Plasma Protein Binding (PPB):	86.296%	Volume Distribution (VD):	-0.056
Fu:	11.133% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.56
BSEP inhibitor:	0.06

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	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:	0.048
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.633
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.554 ? 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):

1.971

Half-life (T1/2):

4.56

ADMET: Toxicity

hERG Blockers:	0.031	hERG Blockers (10um):	0.419
Human Hepatotoxicity (H-HT):	0.462	Drug-induced Liver Injury (DILI):	0.937
AMES Toxicity:	0.675	Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.419	Skin Sensitization:	0.999
Carcinogencity:	0.041	Eye Corrosion:	0.0
Eye Irritation:	0.83	Respiratory Toxicity:	0.026
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.847
Hematotoxicity:	0.009	Drug-induced Nephrotoxicity:	0.14
Genotoxicity:	0.985	RPMI-8226 Immunitoxicity:	0.071
A549 Cytotoxicity:	0.815	Hek293 Cytotoxicity:	0.821
BCF:	0.79 ? 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:	3.629 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.862 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.446 ? 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
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 16712885]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.foodchem.2013.08.121]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[16180814]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	seeds	Shizuoka prefecture, Japan	n.a.	PMID[16499314]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18068204]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21434603]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	flower	n.a.	PMID[21922925]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[21925888]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22377672]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265489]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaves	Bandung, West Java, Indonesia		PMID[23621359]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37255739]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8258	Camellia sinensis	Species	Theaceae	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
IC50	2

Activity Type	# Activity
Others	2

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
NPT1	Others	Radical scavenging activity	n.a.	IC50	=	29200.0	nM	PMID[25993496]
NPT2	Others	Unspecified	n.a.	IC50	=	41500.0	nM	PubChem BioAssay data set

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 NPC162394 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	14129
0.1-0.2	31037
0.2-0.3	3739
0.3-0.4	558
0.4-0.5	172
0.5-0.6	100
0.6-0.7	75
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8364	Intermediate Similarity	NPC249560
0.8273	Intermediate Similarity	NPC487502
0.8247	Intermediate Similarity	NPC89127
0.8	Intermediate Similarity	NPC275977
0.7944	Intermediate Similarity	NPC241781
0.7857	Intermediate Similarity	NPC122467
0.7857	Intermediate Similarity	NPC72554
0.7757	Intermediate Similarity	NPC156785
0.7723	Intermediate Similarity	NPC218161
0.7699	Intermediate Similarity	NPC30011
0.7586	Intermediate Similarity	NPC97817
0.7458	Intermediate Similarity	NPC487501
0.74	Intermediate Similarity	NPC12013
0.74	Intermediate Similarity	NPC11432
0.74	Intermediate Similarity	NPC477613
0.7264	Intermediate Similarity	NPC173837
0.7227	Intermediate Similarity	NPC487500
0.7217	Intermediate Similarity	NPC473554
0.7217	Intermediate Similarity	NPC231787
0.7196	Intermediate Similarity	NPC303694
0.7115	Intermediate Similarity	NPC221342
0.7115	Intermediate Similarity	NPC476470
0.7048	Intermediate Similarity	NPC223426
0.7048	Intermediate Similarity	NPC602448
0.6935	Remote Similarity	NPC33083
0.6931	Remote Similarity	NPC203259
0.6931	Remote Similarity	NPC33054
0.6931	Remote Similarity	NPC176740
0.6931	Remote Similarity	NPC471725
0.6931	Remote Similarity	NPC134532
0.6931	Remote Similarity	NPC602582
0.6916	Remote Similarity	NPC89052
0.6909	Remote Similarity	NPC470718
0.6838	Remote Similarity	NPC487499
0.6814	Remote Similarity	NPC474522
0.6762	Remote Similarity	NPC221288
0.6762	Remote Similarity	NPC194836
0.6762	Remote Similarity	NPC91493
0.6762	Remote Similarity	NPC605081
0.6727	Remote Similarity	NPC470712
0.67	Remote Similarity	NPC95866
0.661	Remote Similarity	NPC21359
0.661	Remote Similarity	NPC460984
0.6609	Remote Similarity	NPC480444
0.6542	Remote Similarity	NPC85751
0.6542	Remote Similarity	NPC19240
0.6522	Remote Similarity	NPC488740
0.6522	Remote Similarity	NPC488736
0.6522	Remote Similarity	NPC488733
0.6514	Remote Similarity	NPC483765
0.6514	Remote Similarity	NPC81042
0.6505	Remote Similarity	NPC173582
0.6505	Remote Similarity	NPC265885
0.6505	Remote Similarity	NPC181465
0.6505	Remote Similarity	NPC215710
0.6505	Remote Similarity	NPC473438
0.6505	Remote Similarity	NPC253788
0.6442	Remote Similarity	NPC155877
0.6422	Remote Similarity	NPC483767
0.6422	Remote Similarity	NPC483769
0.6422	Remote Similarity	NPC483768
0.6422	Remote Similarity	NPC483766
0.641	Remote Similarity	NPC488737
0.6355	Remote Similarity	NPC473327
0.633	Remote Similarity	NPC292929
0.633	Remote Similarity	NPC260504
0.633	Remote Similarity	NPC89809
0.6296	Remote Similarity	NPC101399
0.6296	Remote Similarity	NPC217822
0.6296	Remote Similarity	NPC11847
0.6296	Remote Similarity	NPC198938
0.6293	Remote Similarity	NPC480445
0.6275	Remote Similarity	NPC476215
0.625	Remote Similarity	NPC25946
0.6218	Remote Similarity	NPC192539
0.6216	Remote Similarity	NPC214621
0.6216	Remote Similarity	NPC34267
0.6204	Remote Similarity	NPC104883
0.6204	Remote Similarity	NPC488679
0.6195	Remote Similarity	NPC477895
0.619	Remote Similarity	NPC39834
0.6147	Remote Similarity	NPC142142
0.614	Remote Similarity	NPC217520
0.6132	Remote Similarity	NPC156869
0.6091	Remote Similarity	NPC476472
0.6091	Remote Similarity	NPC294815
0.6091	Remote Similarity	NPC16194
0.6068	Remote Similarity	NPC488734
0.6068	Remote Similarity	NPC488735
0.6068	Remote Similarity	NPC488739
0.6068	Remote Similarity	NPC488732
0.6068	Remote Similarity	NPC488738
0.604	Remote Similarity	NPC216496
0.6038	Remote Similarity	NPC67326
0.6038	Remote Similarity	NPC163242
0.6038	Remote Similarity	NPC272068
0.6017	Remote Similarity	NPC470713
0.6	Remote Similarity	NPC97119
0.6	Remote Similarity	NPC480441
0.5929	Remote Similarity	NPC478277
0.5929	Remote Similarity	NPC96605
0.5929	Remote Similarity	NPC280642
0.5929	Remote Similarity	NPC478276
0.5929	Remote Similarity	NPC478275
0.5929	Remote Similarity	NPC92815
0.5926	Remote Similarity	NPC255157
0.5926	Remote Similarity	NPC35167
0.5926	Remote Similarity	NPC259896
0.5905	Remote Similarity	NPC254855
0.5905	Remote Similarity	NPC116864
0.5905	Remote Similarity	NPC244776
0.5905	Remote Similarity	NPC94610
0.5902	Remote Similarity	NPC480442
0.59	Remote Similarity	NPC127546
0.59	Remote Similarity	NPC57625
0.59	Remote Similarity	NPC173637
0.59	Remote Similarity	NPC317489
0.59	Remote Similarity	NPC223424
0.59	Remote Similarity	NPC600591
0.5872	Remote Similarity	NPC470125
0.5872	Remote Similarity	NPC126784
0.5872	Remote Similarity	NPC241423
0.5862	Remote Similarity	NPC164704
0.5776	Remote Similarity	NPC292019
0.5776	Remote Similarity	NPC202908
0.5763	Remote Similarity	NPC139571
0.5739	Remote Similarity	NPC203145
0.5726	Remote Similarity	NPC470715
0.5726	Remote Similarity	NPC25523
0.5714	Remote Similarity	NPC205824
0.5714	Remote Similarity	NPC482521
0.5714	Remote Similarity	NPC603079
0.5688	Remote Similarity	NPC605592
0.5676	Remote Similarity	NPC477628
0.5664	Remote Similarity	NPC471669
0.5664	Remote Similarity	NPC220173
0.5648	Remote Similarity	NPC471079
0.5619	Remote Similarity	NPC224530
0.5575	Remote Similarity	NPC472991
0.5565	Remote Similarity	NPC480443
0.5545	Remote Similarity	NPC65563
0.5545	Remote Similarity	NPC470949
0.5545	Remote Similarity	NPC304741
0.5537	Remote Similarity	NPC474093
0.5537	Remote Similarity	NPC104910
0.5526	Remote Similarity	NPC477629
0.5524	Remote Similarity	NPC175107
0.5514	Remote Similarity	NPC170052
0.5514	Remote Similarity	NPC135846
0.5495	Remote Similarity	NPC129264
0.5495	Remote Similarity	NPC473571
0.5495	Remote Similarity	NPC110941
0.549	Remote Similarity	NPC111929
0.549	Remote Similarity	NPC320283
0.549	Remote Similarity	NPC41121
0.5487	Remote Similarity	NPC37668
0.5487	Remote Similarity	NPC139060
0.5478	Remote Similarity	NPC36138
0.5446	Remote Similarity	NPC253521
0.5446	Remote Similarity	NPC113836
0.5424	Remote Similarity	NPC189564
0.5398	Remote Similarity	NPC470443
0.5377	Remote Similarity	NPC219904
0.5368	Remote Similarity	NPC482520
0.5368	Remote Similarity	NPC482519
0.5364	Remote Similarity	NPC258044
0.5364	Remote Similarity	NPC217387
0.5364	Remote Similarity	NPC187379
0.536	Remote Similarity	NPC209550
0.5357	Remote Similarity	NPC144097
0.5357	Remote Similarity	NPC186816
0.5345	Remote Similarity	NPC470445
0.5327	Remote Similarity	NPC259957
0.5323	Remote Similarity	NPC470717
0.5315	Remote Similarity	NPC470405
0.531	Remote Similarity	NPC154741
0.528	Remote Similarity	NPC470720
0.5259	Remote Similarity	NPC473073
0.5238	Remote Similarity	NPC145038
0.5238	Remote Similarity	NPC56077
0.5238	Remote Similarity	NPC281131
0.5238	Remote Similarity	NPC253662
0.5238	Remote Similarity	NPC179950
0.5238	Remote Similarity	NPC88789
0.5238	Remote Similarity	NPC491374
0.5217	Remote Similarity	NPC270448
0.52	Remote Similarity	NPC470719
0.5192	Remote Similarity	NPC135599
0.5192	Remote Similarity	NPC73855
0.5192	Remote Similarity	NPC113968
0.5192	Remote Similarity	NPC328940
0.5192	Remote Similarity	NPC277174
0.5192	Remote Similarity	NPC606877
0.5179	Remote Similarity	NPC471748
0.5175	Remote Similarity	NPC61904
0.5175	Remote Similarity	NPC488073
0.5175	Remote Similarity	NPC472992
0.5175	Remote Similarity	NPC153755
0.5175	Remote Similarity	NPC488074

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC162394 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4407
0.1-0.2	4689
0.2-0.3	44
0.3-0.4	5
0.4-0.5	3
0.5-0.6	1
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
0.6931	Remote Similarity	NPD6797	Phase 2
0.5391	Remote Similarity	NPD7251	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