NPASS Compound

Natural Product: NPC138993

Natural Product ID	NPC138993
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Verproside
IUPAC Name	[(1aS,1bS,2S,5aR,6S,6aS)-1a-(hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-6-yl] 3,4-dihydroxybenzoate
Synonyms	Verproside
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1082144
PubChem CID	12000799
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

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 61 65 0 0 0 0 0 0 0 0999 V2000 6.0828 -0.1296 0.3041 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4357 -0.1907 0.5354 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9898 -1.4609 0.6572 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2317 -2.5940 0.5527 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8838 -2.4810 0.3211 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2899 -1.2336 0.1933 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8693 -1.0809 -0.0531 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0972 -2.0540 -0.1564 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3325 0.1790 -0.1811 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9813 0.3682 -0.4166 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2349 1.2317 0.5390 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1178 0.6871 1.8993 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3151 -0.3468 2.0579 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3379 -0.8198 0.9420 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8966 0.0638 -0.0348 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1274 1.3184 -0.1777 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3756 1.5742 -1.5874 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5585 2.0834 -2.6487 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7173 1.3737 -2.7990 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6753 1.0515 -1.7381 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5755 2.4512 -1.5777 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2191 0.2791 0.3589 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1522 -0.3043 -0.4740 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8473 -1.4169 0.3116 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5252 -0.7775 1.4916 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2753 0.4633 1.1242 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3023 0.6023 -0.3672 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9777 1.9259 -0.7553 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0650 1.9068 -2.1541 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0738 0.5722 -0.9609 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5981 0.3216 1.5487 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5984 -0.5565 2.5135 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7287 -2.0987 -0.5135 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8570 -3.8453 0.6858 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3525 -1.5824 0.8920 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6110 0.8571 0.2034 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0485 0.6991 0.6212 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2843 -3.3642 0.2381 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4812 -0.6218 -0.4622 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5896 2.2832 0.5622 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6764 1.1328 2.7165 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1737 -0.7996 3.0034 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9084 -0.5134 -0.9710 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6666 2.2370 0.1297 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0707 2.2042 -3.6230 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8581 3.1293 -2.3405 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1550 1.5577 -3.6670 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1758 0.6428 -2.6132 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6781 -0.8351 -1.3327 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0407 -2.1238 0.6654 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2262 -1.5533 1.9028 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8794 1.3710 1.6346 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0035 -0.1867 -0.7625 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9917 1.9650 -0.2946 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3553 2.7760 -0.4095 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3494 0.9918 -2.3879 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6842 0.6855 2.4801 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4052 0.4038 2.6550 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3715 -2.5907 0.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9587 -4.2453 1.5922 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9482 -1.5824 0.0784 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 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 18 19 1 0 17 20 1 0 20 21 1 0 15 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 26 31 1 0 25 32 1 0 24 33 1 0 4 34 1 0 3 35 1 0 6 1 1 0 20 10 1 0 30 23 1 0 16 11 1 0 21 17 1 0 1 36 1 0 2 37 1 0 5 38 1 0 10 39 1 6 11 40 1 1 12 41 1 0 13 42 1 0 15 43 1 6 16 44 1 1 18 45 1 0 18 46 1 0 19 47 1 0 20 48 1 6 23 49 1 6 24 50 1 1 25 51 1 1 26 52 1 1 27 53 1 6 28 54 1 0 28 55 1 0 29 56 1 0 31 57 1 0 32 58 1 0 33 59 1 0 34 60 1 0 35 61 1 0 M END

Standard InCHIKey	DBUOUVZMYWYRRI-YWEKDMGLSA-N
Standard InCHI	InChI=1S/C22H26O13/c23-6-12-14(27)15(28)16(29)21(32-12)34-20-13-9(3-4-31-20)17(18-22(13,7-24)35-18)33-19(30)8-1-2-10(25)11(26)5-8/h1-5,9,12-18,20-21,23-29H,6-7H2/t9-,12-,13-,14-,15+,16-,17+,18+,20+,21+,22-/m1/s1
SMILES	c1cc(c(cc1C(=O)O[C@H]1[C@@H]2C=CO[C@H]([C@@H]2[C@]2(CO)[C@H]1O2)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	498.14	Volume:	447.376 ? Van der Waals volume.
Dense:	1.113	LogP:	-0.902 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.222 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.324 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	25.0
TPSA:	208.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.125	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.987	Fsp³:	0.591
MCE-18:	116.114 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.544	Fluc inhibitor:	0.252 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.053 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.025 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.438	Promiscuous compounds:	0.354

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.5	MDCK Permeability:	-5.246
Pgp-inhibitor:	0.0	Pgp-substrate:	0.373
PAMPA:	0.996 ? 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):	0.368
20% Bioavailability (F20%):	0.851	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014	MRP1:	0.827
Plasma Protein Binding (PPB):	55.29%	Volume Distribution (VD):	-0.53
Fu:	46.914% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.03
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.656
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):

2.532

Half-life (T1/2):

3.311

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.236
Human Hepatotoxicity (H-HT):	0.407	Drug-induced Liver Injury (DILI):	0.814
AMES Toxicity:	0.905	Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.017	Skin Sensitization:	1.0
Carcinogencity:	0.158	Eye Corrosion:	0.001
Eye Irritation:	0.476	Respiratory Toxicity:	0.013
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.976
Hematotoxicity:	0.203	Drug-induced Nephrotoxicity:	0.268
Genotoxicity:	0.239	RPMI-8226 Immunitoxicity:	0.034
A549 Cytotoxicity:	0.52	Hek293 Cytotoxicity:	0.149
BCF:	0.431 ? 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:	3.178 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.007 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.0 ? 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
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(79)80020-5]
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[10328294]
NPO12175	Iostephane heterophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473422]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568764]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	pericarp	n.a.	n.a.	PMID[16038565]
NPO12653	Diacarnus levii	Species	Podospongiidae	Eukaryota	n.a.	at a depth of -10 M off the coast of Papua New Guinea	1998-JUN	PMID[17253866]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17944538]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18166016]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20232858]
NPO30110	Veronica lavaudiana	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21568305]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22823026]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	leaves and stems	Ha Long, Quang Ninh province, Vietnam	2014-Jul	PMID[25769817]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29792702]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30892891]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	xylem	n.a.	Database[Article]
NPO3432	Tovomita brasiliensis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12175	Iostephane heterophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4129	Veronica persica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12526	Veronica turrilliana	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2289	Vicia hirsuta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12762	Elattostachys apetala	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7323	Lindera pipericarpa	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5908	Dianella tasmanica	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7648	Geigeria plumosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11674	Viburnum lantanoides	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12653	Diacarnus levii	Species	Podospongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5311	Isertia haenkeana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1790	Plectranthus comosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3671	Rhodiola coccinea	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2289	Vicia hirsuta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4129	Veronica persica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4129	Veronica persica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3671	Rhodiola coccinea	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2289	Vicia hirsuta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2576	Eusideroxylon zwageri	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11674	Viburnum lantanoides	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14776	Petrosia weinbergi	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7323	Lindera pipericarpa	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12526	Veronica turrilliana	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11397	Cladophora rupestris	Species	Cladophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4129	Veronica persica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9550	Eritrichium incanum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5311	Isertia haenkeana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12047	Solanum unguiculatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4923	Ononis hircina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11255	Veronica thomsonii	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2289	Vicia hirsuta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11491	Vellozia declinans	Species	Velloziaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10102	Pithecellobium albicans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14462	Jasonia tuberosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7648	Geigeria plumosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12653	Diacarnus levii	Species	Podospongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5908	Dianella tasmanica	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9561	Preussia australis	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13096	Lecidea kochiana	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1455	Aspergillus caelatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10553	Heterophyllaea pustulata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9908	Adenium somalense	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9254	Scutellaria racemosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO396	Ventilago goughii	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12175	Iostephane heterophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1790	Plectranthus comosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13466	Atroxima afzeliana	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26737	Solanum mauritianum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3432	Tovomita brasiliensis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3671	Rhodiola coccinea	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12762	Elattostachys apetala	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1314	Goodenia strophiolata	Species	Goodeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5173	Antidesma pentandrum	Species	Phyllanthaceae	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
Activity	2

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT861	Individual protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	107.1	%	PMID[26508549]
NPT861	Individual protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	88.3	%	PMID[26508549]

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 NPC138993 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	15777
0.1-0.2	29964
0.2-0.3	3633
0.3-0.4	438
0.4-0.5	31
0.5-0.6	3
0.6-0.7	7
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8696	High Similarity	NPC194705
0.8133	Intermediate Similarity	NPC301910
0.7895	Intermediate Similarity	NPC130730
0.7532	Intermediate Similarity	NPC18789
0.75	Intermediate Similarity	NPC206815
0.6875	Remote Similarity	NPC46644
0.6765	Remote Similarity	NPC107594
0.6667	Remote Similarity	NPC89693
0.6667	Remote Similarity	NPC475824
0.6625	Remote Similarity	NPC486494
0.6395	Remote Similarity	NPC229548
0.6118	Remote Similarity	NPC474234
0.5976	Remote Similarity	NPC229354
0.5222	Remote Similarity	NPC486495
0.5176	Remote Similarity	NPC473149

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC138993 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5150
0.1-0.2	3943
0.2-0.3	54
0.3-0.4	2
0.4-0.5	1
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