NPASS Compound

Natural Product: NPC291638

Natural Product ID	NPC291638
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PBBYYGCXAHKQFJ-YLMNRMNTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL364252
PubChem CID	14414924
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

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 79 82 0 0 0 0 0 0 0 0999 V2000 -5.0435 2.0116 -1.0810 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8982 1.2718 -1.7216 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9642 0.9668 -2.9242 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8022 0.9437 -0.9809 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7453 0.2711 -1.5361 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5764 -0.0507 -0.6456 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3833 -0.7765 -1.5603 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6979 -0.4984 -1.1762 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6436 0.0995 -1.9726 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3319 0.4292 -3.1388 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9752 0.3356 -1.4512 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3767 0.0057 -0.1759 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6473 0.2393 0.2917 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5929 0.8251 -0.5108 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2232 1.1719 -1.8051 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9433 0.9299 -2.2575 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1165 -2.2459 -1.7122 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3335 -2.9521 -0.4943 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5686 -2.1579 0.0047 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8664 -0.9561 0.5170 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4270 -1.3911 0.9236 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5518 -2.7207 0.6986 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0930 -3.6100 1.8446 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9884 -3.1274 0.4323 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4796 -0.3288 1.7231 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2288 1.1508 1.8821 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0469 1.5631 1.2121 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0957 1.2393 -0.2486 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5460 2.3391 -0.9136 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0958 3.2190 -1.7319 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3091 3.0965 -1.9405 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6449 4.3446 -2.3920 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2919 2.9210 1.4834 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3664 3.3711 2.2516 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1232 2.4832 2.7004 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6128 4.7950 2.5290 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9477 -0.5534 1.9249 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1460 -3.0058 0.9651 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3902 -3.5554 0.8138 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0888 -3.3351 -0.1905 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9137 -4.4404 1.8869 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9992 1.4920 -1.3426 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1001 3.0123 -1.5587 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9000 2.0720 0.0148 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3077 0.9725 -2.3185 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1082 -0.5725 -2.1521 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2901 -0.3588 -2.6127 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6395 -0.4553 0.4671 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9108 -0.0359 1.2927 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6033 1.0203 -0.1651 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9658 1.6299 -2.4296 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6322 1.1967 -3.2768 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0231 -2.6817 -2.1957 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6928 -2.3796 -2.4899 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5831 -3.9826 -0.6919 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2855 -2.0290 -0.7971 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4942 -3.1040 2.6050 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4183 -4.5132 1.4030 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9693 -4.0608 2.3995 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1502 -4.2071 0.7344 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7106 -2.5709 1.0637 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2617 -3.1191 -0.6403 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0106 -0.7845 2.6548 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1103 1.7352 1.5477 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1180 1.4129 2.9581 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8571 0.9970 1.7224 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1522 1.3023 -0.5602 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0802 5.2872 -2.2695 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7286 4.0952 -3.4556 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6787 4.4031 -1.9875 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6395 5.3236 2.4432 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9953 4.9644 3.5520 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3420 5.2470 1.8285 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5532 -0.7039 1.0434 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1702 -1.3701 2.6772 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4112 0.3461 2.4392 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2288 -5.4245 1.5193 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1603 -4.6018 2.6838 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7531 -3.8723 2.3705 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 6 5 1 6 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 7 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 21 22 1 0 22 23 1 0 22 24 1 0 20 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 27 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 25 37 1 0 19 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 28 6 1 0 20 6 1 0 16 11 1 0 22 18 1 0 1 42 1 0 1 43 1 0 1 44 1 0 5 45 1 0 5 46 1 0 7 47 1 6 12 48 1 0 13 49 1 0 14 50 1 0 15 51 1 0 16 52 1 0 17 53 1 0 17 54 1 0 18 55 1 6 19 56 1 6 23 57 1 0 23 58 1 0 23 59 1 0 24 60 1 0 24 61 1 0 24 62 1 0 25 63 1 1 26 64 1 0 26 65 1 0 27 66 1 1 28 67 1 6 32 68 1 0 32 69 1 0 32 70 1 0 36 71 1 0 36 72 1 0 36 73 1 0 37 74 1 0 37 75 1 0 37 76 1 0 41 77 1 0 41 78 1 0 41 79 1 0 M END

Standard InCHIKey	PBBYYGCXAHKQFJ-YLMNRMNTSA-N
Standard InCHI	InChI=1S/C30H38O11/c1-16-13-23(37-18(3)32)26(39-20(5)34)29(15-36-17(2)31)24(40-27(35)21-11-9-8-10-12-21)14-22-25(38-19(4)33)30(16,29)41-28(22,6)7/h8-12,16,22-26H,13-15H2,1-7H3/t16-,22-,23+,24+,25-,26+,29-,30-/m1/s1
SMILES	CC(=O)OC[C@@]12[C@@H](OC(=O)c3ccccc3)C[C@@H]3[C@H]([C@]2(OC3(C)C)[C@@H](C[C@@H]([C@@H]1OC(=O)C)OC(=O)C)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	574.24	Volume:	568.811 ? Van der Waals volume.
Dense:	1.01	LogP:	2.818 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.854 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.243 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	25.0
TPSA:	140.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.35	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.843	Fsp³:	0.633
MCE-18:	146.816 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.434	Fluc inhibitor:	0.139 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.02 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.223	Promiscuous compounds:	0.2

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.037	MDCK Permeability:	-4.679
Pgp-inhibitor:	0.944	Pgp-substrate:	0.163
PAMPA:	0.086 ? 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%):	0.011	30% Bioavailability (F30%):	0.173
50% Bioavailability (F50%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.803	MRP1:	0.999
Plasma Protein Binding (PPB):	73.613%	Volume Distribution (VD):	-0.361
Fu:	24.544% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.983	BCRP inhibitor:	0.04
BSEP inhibitor:	0.774

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.172
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.01
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.16
CYP3A4-inhibitor:	0.029	CYP3A4-substrate:	0.062
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.995 ? 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):

1.994

Half-life (T1/2):

1.111

ADMET: Toxicity

hERG Blockers:	0.019	hERG Blockers (10um):	0.263
Human Hepatotoxicity (H-HT):	0.088	Drug-induced Liver Injury (DILI):	0.828
AMES Toxicity:	0.908	Rat Oral Acute Toxicity:	0.312
Maximum Recommended Daily Dose:	0.194	Skin Sensitization:	0.997
Carcinogencity:	0.845	Eye Corrosion:	0.005
Eye Irritation:	0.378	Respiratory Toxicity:	0.044
Drug-induced Neurotoxicity:	0.601	Ototoxicity:	0.215
Hematotoxicity:	0.291	Drug-induced Nephrotoxicity:	0.568
Genotoxicity:	0.502	RPMI-8226 Immunitoxicity:	0.084
A549 Cytotoxicity:	0.487	Hek293 Cytotoxicity:	0.552
BCF:	0.574 ? 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:	3.611 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.207 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.758 ? 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
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	stem	n.a.	PMID[15467233]
NPO33107	zinowiewia costaricensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974580]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	stem	n.a.	n.a.	PMID[18471021]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[18471021]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	Stems	n.a.	n.a.	PMID[19534471]
NPO10464	Epipedobates anthonyi	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337496]
NPO23441	Schisandra sphaerandra	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[8778243]
NPO21610	Laurencia rigida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358636]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20787	Achyranthes aspera	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22272	Raphanus raphanistrum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO33107	zinowiewia costaricensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6425	Betula davurica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22788	Barnettia kerrii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3277	Salix alba	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21776	Sesbania grandiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21610	Laurencia rigida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22212	Rhizophora mangle	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20787	Achyranthes aspera	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5933	Drimia fugax	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23441	Schisandra sphaerandra	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20787	Achyranthes aspera	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10464	Epipedobates anthonyi	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22670	Phebalium bilobum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19561	Garcinia conrauana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21610	Laurencia rigida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22788	Barnettia kerrii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6425	Betula davurica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20787	Achyranthes aspera	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22212	Rhizophora mangle	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14938	Cybister lateralimarginalis	Species	Dytiscidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22734	Neopringlea integrifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23441	Schisandra sphaerandra	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22915	Stereocaulon azoreum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22272	Raphanus raphanistrum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8518	Colchicum luteum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17102	Ocypus olens	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11536	Xanthocephalum benthamianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3277	Salix alba	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21776	Sesbania grandiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10749	Capnella thyrsoidea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5933	Drimia fugax	Species	Hyacinthaceae	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
Ki	3
Imax	1
FR50	2
Activity	5

Activity Type	# Activity
Cell line	2
Organism	2
Individual protein	3
Others	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ki	=	2360.0	nM	PMID[17850057]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Imax	=	80.8	%	PMID[17850057]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ki	=	2344.23	nM	PMID[17850057]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT886	Cell line	NIH3T3	Mus musculus	Ki	=	2357.0	nM	PMID[15974580]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[26854381]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	FR50	=	0.54	n.a.	DOI[10.1016/0305-1978(92)90042-C]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	FR50	=	0.19	n.a.	DOI[10.1016/0305-1978(92)90042-C]
NPT2	Others	Unspecified	n.a.	Activity	=	0.0	%	PMID[26854381]
NPT2	Others	Unspecified	n.a.	Activity	=	33.6	%	PMID[26854381]
NPT2	Others	Unspecified	n.a.	Activity	=	78.5	%	PMID[26854381]
NPT2	Others	Unspecified	n.a.	Activity	=	97.2	%	PMID[26854381]

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 NPC291638 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	16503
0.1-0.2	31334
0.2-0.3	1451
0.3-0.4	397
0.4-0.5	83
0.5-0.6	45
0.6-0.7	22
0.7-0.8	0
0.8-0.85	3
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC479047
0.9333	High Similarity	NPC4341
0.9194	High Similarity	NPC479044
0.8871	High Similarity	NPC43241
0.871	High Similarity	NPC191082
0.8333	Intermediate Similarity	NPC184747
0.8281	Intermediate Similarity	NPC139067
0.8281	Intermediate Similarity	NPC177340
0.7727	Intermediate Similarity	NPC67777
0.7619	Intermediate Similarity	NPC195647
0.7424	Intermediate Similarity	NPC17877
0.7313	Intermediate Similarity	NPC147880
0.72	Intermediate Similarity	NPC75600
0.72	Intermediate Similarity	NPC483884
0.7101	Intermediate Similarity	NPC471100
0.7101	Intermediate Similarity	NPC605884
0.7077	Intermediate Similarity	NPC473081
0.7077	Intermediate Similarity	NPC200592
0.7077	Intermediate Similarity	NPC610542
0.7042	Intermediate Similarity	NPC97667
0.7	Intermediate Similarity	NPC41481
0.6957	Remote Similarity	NPC148062
0.6912	Remote Similarity	NPC473060
0.6806	Remote Similarity	NPC70716
0.6806	Remote Similarity	NPC95265
0.6714	Remote Similarity	NPC27377
0.662	Remote Similarity	NPC254558
0.662	Remote Similarity	NPC471107
0.6571	Remote Similarity	NPC48017
0.6567	Remote Similarity	NPC270498
0.6479	Remote Similarity	NPC147217
0.6479	Remote Similarity	NPC137718
0.6429	Remote Similarity	NPC483902
0.6429	Remote Similarity	NPC51314
0.6429	Remote Similarity	NPC472577
0.64	Remote Similarity	NPC479042
0.6267	Remote Similarity	NPC473112
0.6267	Remote Similarity	NPC607428
0.6216	Remote Similarity	NPC479043
0.6164	Remote Similarity	NPC171207
0.6164	Remote Similarity	NPC473673
0.6111	Remote Similarity	NPC246480
0.6053	Remote Similarity	NPC473613
0.5942	Remote Similarity	NPC474608
0.589	Remote Similarity	NPC90257
0.589	Remote Similarity	NPC483845
0.589	Remote Similarity	NPC69357
0.5867	Remote Similarity	NPC472574
0.5844	Remote Similarity	NPC473085
0.5833	Remote Similarity	NPC294512
0.5823	Remote Similarity	NPC14499
0.5802	Remote Similarity	NPC610134
0.5789	Remote Similarity	NPC266265
0.5775	Remote Similarity	NPC481047
0.5775	Remote Similarity	NPC481045
0.575	Remote Similarity	NPC479040
0.5714	Remote Similarity	NPC96903
0.5676	Remote Similarity	NPC483883
0.5676	Remote Similarity	NPC151585
0.5658	Remote Similarity	NPC92293
0.5658	Remote Similarity	NPC483844
0.5647	Remote Similarity	NPC176413
0.5647	Remote Similarity	NPC483885
0.5581	Remote Similarity	NPC483868
0.557	Remote Similarity	NPC483849
0.5493	Remote Similarity	NPC283375
0.5493	Remote Similarity	NPC183122
0.5493	Remote Similarity	NPC481066
0.5465	Remote Similarity	NPC479045
0.5443	Remote Similarity	NPC483848
0.5432	Remote Similarity	NPC88593
0.5395	Remote Similarity	NPC483842
0.5385	Remote Similarity	NPC252314
0.5385	Remote Similarity	NPC11685
0.5385	Remote Similarity	NPC16912
0.5333	Remote Similarity	NPC70973
0.5256	Remote Similarity	NPC306146
0.5256	Remote Similarity	NPC483841
0.519	Remote Similarity	NPC57628
0.519	Remote Similarity	NPC472569
0.519	Remote Similarity	NPC472570
0.519	Remote Similarity	NPC609924
0.5185	Remote Similarity	NPC481489
0.5132	Remote Similarity	NPC163087
0.5132	Remote Similarity	NPC473111
0.5072	Remote Similarity	NPC216137
0.5063	Remote Similarity	NPC471103
0.5062	Remote Similarity	NPC472568

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC291638 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3433
0.1-0.2	5530
0.2-0.3	186
0.3-0.4	1
0.4-0.5	0
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