NPASS Compound

Natural Product: NPC139037

Natural Product ID	NPC139037
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FYGDTMLNYKFZSV-MRCIVHHJSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	62698
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

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 66 68 0 0 0 0 0 0 0 0999 V2000 5.7887 -2.5934 -0.1822 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2323 -1.2279 -0.5753 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3681 -0.2441 -0.4585 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8118 1.0901 -0.0064 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4398 1.2235 -0.6830 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5411 0.2377 0.0231 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1864 -0.9602 0.2854 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3780 -0.0351 -0.6763 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2303 0.3014 0.0023 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2704 -0.8443 0.1830 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1446 -1.0030 1.6395 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9688 -0.9941 2.4787 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7841 -0.8459 -0.6769 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6006 0.2565 -0.6363 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9170 1.5421 -0.3566 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5495 1.4169 -0.7917 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2349 2.5990 -0.6458 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4474 2.5734 -1.1320 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6659 -0.0445 0.1750 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8828 -0.1541 -0.3972 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8612 0.7199 0.3744 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3018 2.0855 0.6625 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1733 2.7145 1.5496 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1167 0.7389 -0.1914 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3877 -0.3650 -0.9784 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8592 -1.6537 -0.4038 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3661 -1.5962 -0.1741 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6776 -2.4426 -1.0140 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5024 -1.9889 0.7649 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7796 -0.4918 -1.0778 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6067 0.9503 -2.0230 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6188 1.0106 1.3753 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9069 -0.0571 -1.7254 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2401 -2.5698 1.1426 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0368 -3.3889 -0.2564 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6503 -2.8782 -0.8183 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8624 -1.3382 -1.6220 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1266 -0.5686 0.2835 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4697 1.9331 -0.2812 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1316 2.2754 -0.5017 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3216 0.6919 1.0335 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4330 0.7393 1.0064 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8674 -1.7785 -0.0445 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6467 -1.9785 1.8084 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8875 -0.2265 1.9371 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9206 -0.2915 3.1597 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0296 0.3495 -1.6812 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8848 1.8369 0.7047 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5089 1.1639 -1.8724 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4961 3.0239 -1.4935 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0540 2.1927 -1.8086 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9348 0.0072 -1.4838 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9741 0.2119 1.3769 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1131 2.6722 -0.2406 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3453 1.9424 1.2024 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9887 2.2130 1.7298 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9536 -0.1765 -1.9741 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0461 -2.4481 -1.1493 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1004 -1.8505 0.8721 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3016 -2.9435 -1.6050 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4537 -2.2196 0.5776 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2101 0.3604 -1.3386 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7049 1.8192 -2.4996 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2479 1.8710 1.7093 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0753 0.8943 -1.9264 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1662 -3.4598 1.5683 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 10 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 15 18 1 0 14 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 25 30 1 0 5 31 1 0 4 32 1 0 3 33 1 0 1 34 1 0 7 2 1 0 16 9 1 0 27 20 1 0 1 35 1 0 1 36 1 0 2 37 1 6 3 38 1 1 4 39 1 1 5 40 1 6 6 41 1 0 9 42 1 1 10 43 1 6 11 44 1 0 11 45 1 0 12 46 1 0 14 47 1 0 15 48 1 1 16 49 1 6 17 50 1 0 18 51 1 0 20 52 1 6 21 53 1 1 22 54 1 0 22 55 1 0 23 56 1 0 25 57 1 6 26 58 1 6 27 59 1 1 28 60 1 0 29 61 1 0 30 62 1 0 31 63 1 0 32 64 1 0 33 65 1 0 34 66 1 0 M END

Standard InCHIKey	FYGDTMLNYKFZSV-MRCIVHHJSA-N
Standard InCHI	InChI=1S/C18H32O16/c19-1-4-7(22)8(23)12(27)17(31-4)34-15-6(3-21)32-18(13(28)10(15)25)33-14-5(2-20)30-16(29)11(26)9(14)24/h4-29H,1-3H2/t4-,5-,6-,7-,8+,9-,10-,11-,12-,13-,14-,15-,16+,17?,18?/m1/s1
SMILES	C([C@@H]1[C@H]([C@@H]([C@H](C(O1)O[C@@H]1[C@@H](CO)OC([C@@H]([C@H]1O)O)O[C@@H]1[C@@H](CO)O[C@@H]([C@@H]([C@H]1O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	504.17	Volume:	434.858 ? Van der Waals volume.
Dense:	1.159	LogP:	-4.085 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-3.238 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	0.347 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	18.0
TPSA:	268.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	11.0	Rings:	3.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.154	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.74	Fsp³:	1.0
MCE-18:	68.0 ? 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:	0.299	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.024 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.615	Promiscuous compounds:	0.005

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.301	MDCK Permeability:	-4.8
Pgp-inhibitor:	0.0	Pgp-substrate:	0.961
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.251	30% Bioavailability (F30%):	0.992
50% Bioavailability (F50%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016	MRP1:	0.005
Plasma Protein Binding (PPB):	20.145%	Volume Distribution (VD):	-0.49
Fu:	85.808% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.004
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.946
HLM stability:	0.006 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

0.516

Half-life (T1/2):

3.19

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.021
Human Hepatotoxicity (H-HT):	0.53	Drug-induced Liver Injury (DILI):	0.764
AMES Toxicity:	0.934	Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.022	Eye Corrosion:	0.0
Eye Irritation:	0.12	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.995
Hematotoxicity:	0.212	Drug-induced Nephrotoxicity:	0.954
Genotoxicity:	0.14	RPMI-8226 Immunitoxicity:	0.173
A549 Cytotoxicity:	0.065	Hek293 Cytotoxicity:	0.021
BCF:	-0.193 ? 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:	0.802 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	1.936 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	1.092 ? 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
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11356-018-3422-z]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1111/j.1365-3040.1996.tb00393.x]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15516765]
NPO2746	Apis cerana	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16377847]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18270436]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20973550]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23700450]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23793896]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23849114]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24310066]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[24967651]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25433632]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[26860358]
NPO27364	Gallus gallus	Species	Phasianidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27439360]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38792127]
NPO2746	Apis cerana	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27364	Gallus gallus	Species	Phasianidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9788	Coffea arabica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9788	Coffea arabica	Species	Rubiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Protoplast	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO9788	Coffea arabica	Species	Rubiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9788	Coffea arabica	Species	Rubiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9788	Coffea arabica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2746	Apis cerana	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27364	Gallus gallus	Species	Phasianidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO2746	Apis cerana	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8319	Massa fermentata hordei germinatus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO2746	Apis cerana	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5264	Dens draconis preparata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9788	Coffea arabica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27364	Gallus gallus	Species	Phasianidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2746	Apis cerana	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27364	Gallus gallus	Species	Phasianidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27364	Gallus gallus	Species	Phasianidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9788	Coffea arabica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2746	Apis cerana	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8541	Oryza sativa	Species	Poaceae	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
NPO8541	Oryza sativa	Other	Seed	1805	1560	2050	mg/100g	Database [DUKE]
NPO9788	Coffea arabica	Other	Seed	870	870	870	mg/100g	Database [DUKE]

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 NPC139037 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	37841
0.1-0.2	8965
0.2-0.3	2715
0.3-0.4	272
0.4-0.5	33
0.5-0.6	20
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	5
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC317023
1.0	High Similarity	NPC489878
0.8947	High Similarity	NPC246558
0.8947	High Similarity	NPC67660
0.8947	High Similarity	NPC165198
0.8947	High Similarity	NPC209753
0.8947	High Similarity	NPC58629
0.6053	Remote Similarity	NPC6848
0.5918	Remote Similarity	NPC477750
0.5918	Remote Similarity	NPC477763
0.5918	Remote Similarity	NPC477757
0.5918	Remote Similarity	NPC477762
0.5918	Remote Similarity	NPC477755
0.5918	Remote Similarity	NPC477753
0.55	Remote Similarity	NPC23134
0.5472	Remote Similarity	NPC477764
0.537	Remote Similarity	NPC477752
0.537	Remote Similarity	NPC477751
0.537	Remote Similarity	NPC477756
0.5273	Remote Similarity	NPC477761
0.5238	Remote Similarity	NPC482833
0.5238	Remote Similarity	NPC314306
0.5238	Remote Similarity	NPC314350
0.5179	Remote Similarity	NPC477758
0.5179	Remote Similarity	NPC477760
0.5179	Remote Similarity	NPC477754
0.5098	Remote Similarity	NPC604425
0.5088	Remote Similarity	NPC477759

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC139037 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8409
0.1-0.2	640
0.2-0.3	67
0.3-0.4	14
0.4-0.5	11
0.5-0.6	2
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8947	High Similarity	NPD888	Phase 3
0.8947	High Similarity	NPD890	Clinical (unspecified phase)
0.8947	High Similarity	NPD891	Phase 3
0.8947	High Similarity	NPD892	Phase 3
0.8947	High Similarity	NPD893	Approved
0.5238	Remote Similarity	NPD6429	Phase 4
0.5238	Remote Similarity	NPD6430	Approved

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