NPASS Compound

Natural Product: NPC224121

Natural Product ID	NPC224121
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-[Beta-D-Glucuronopyranosyl]Soyasapogenol B
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL450401
PubChem CID	44566984
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 103108 0 0 0 0 0 0 0 0999 V2000 2.4080 0.7726 3.3146 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9179 -0.5092 3.0887 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8232 -0.7023 1.5533 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3757 -2.0864 1.3270 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6435 0.3314 0.9155 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8672 1.5623 0.4759 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4876 1.3772 0.0377 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9930 -0.0672 -0.1026 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3630 -0.7032 1.1866 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6805 -2.0240 1.3671 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8104 -1.6675 1.5133 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3254 -1.1181 0.1712 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5055 0.0513 -0.2077 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9431 0.6134 -1.5064 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4156 0.8028 -1.4705 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2639 0.2284 -0.6355 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7634 -0.7172 0.4079 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8778 -0.1762 1.8127 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6504 -1.9546 0.3680 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1113 -1.5387 0.5972 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5217 -0.7050 -0.5578 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7034 0.5278 -0.8128 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1939 1.7595 -0.1412 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6553 2.0042 -0.3896 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3284 0.8970 -1.1674 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9935 -0.3896 -0.4079 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8106 -1.3880 -0.9358 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8965 3.2832 -1.1993 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4454 2.1790 0.8959 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4189 -1.5633 -1.8256 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3236 -2.2856 -0.7524 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6508 -0.6207 -1.3191 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4307 -0.1621 -0.0867 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7872 0.1040 -0.0161 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1660 0.9759 -1.0501 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3739 1.5523 -0.6723 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6968 2.7590 -1.4308 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9046 3.1640 -2.3165 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8557 3.4767 -1.2046 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4450 0.4934 -0.8942 C 0 0 2 0 0 0 0 0 0 0 0 0 8.1299 -0.7155 -0.0877 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6774 -1.0971 -0.0072 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5417 -1.7009 1.2753 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7875 -1.8147 -0.6826 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6837 0.9976 -0.4676 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1074 0.9095 4.2369 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2615 -1.2303 3.5797 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9666 -0.5463 3.4112 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9904 -2.1540 0.4055 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0763 -2.3381 2.1799 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6267 -2.8969 1.3685 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3772 0.7666 1.6609 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5341 2.0375 -0.3090 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8740 2.3536 1.2875 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3380 1.9297 -0.9176 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7597 1.8847 0.7450 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8750 -0.0300 1.9644 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9456 -2.4421 2.3551 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8380 -2.7682 0.5871 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3058 -2.5819 1.8231 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7768 -0.8567 2.2915 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7708 0.8505 0.5636 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4869 1.5956 -1.7539 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7589 -0.0243 -2.3990 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8733 1.4977 -2.2170 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1506 0.6209 2.0446 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7640 -1.0705 2.5013 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8608 0.2044 2.0908 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6788 -2.3970 -0.6546 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4118 -2.6767 1.1473 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2970 -1.1371 1.5838 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6790 -2.4949 0.5304 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9231 0.7534 -1.9161 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6468 2.6254 -0.6277 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0197 1.8798 0.9164 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4186 1.0318 -1.0992 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9690 0.8437 -2.2131 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2483 -0.2601 0.6419 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1202 -1.1766 -1.8325 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0013 3.4379 -1.8331 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7676 3.1674 -1.8690 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0990 4.1229 -0.5174 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9952 1.6677 1.7527 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5085 1.8249 0.7752 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5426 3.2679 1.1623 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4429 -1.3750 -2.3382 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6096 -2.6169 -1.6338 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1934 -1.1995 -2.5347 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7577 -3.1518 -0.1644 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8931 -2.1198 -1.6879 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3359 -2.6608 -1.0625 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3220 0.1060 -1.8434 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9552 -0.9483 -2.1157 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2865 -1.5075 -1.1232 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9667 0.6771 0.9129 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3447 1.7203 0.4288 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9823 4.4510 -1.4452 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5347 0.2201 -1.9550 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5864 -0.6648 0.9465 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3976 -1.8432 -0.7877 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5008 -2.6725 1.2074 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7548 -1.7613 -0.5414 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3723 0.9492 -1.1672 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 1 3 4 1 0 3 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 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 24 28 1 0 24 29 1 0 21 30 1 6 12 31 1 6 8 32 1 6 5 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 36 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 9 3 1 0 17 12 1 0 26 21 1 0 42 34 1 0 13 8 1 0 22 16 1 0 1 46 1 0 2 47 1 0 2 48 1 0 4 49 1 0 4 50 1 0 4 51 1 0 5 52 1 1 6 53 1 0 6 54 1 0 7 55 1 0 7 56 1 0 9 57 1 1 10 58 1 0 10 59 1 0 11 60 1 0 11 61 1 0 13 62 1 1 14 63 1 0 14 64 1 0 15 65 1 0 18 66 1 0 18 67 1 0 18 68 1 0 19 69 1 0 19 70 1 0 20 71 1 0 20 72 1 0 22 73 1 6 23 74 1 0 23 75 1 0 25 76 1 0 25 77 1 0 26 78 1 1 27 79 1 0 28 80 1 0 28 81 1 0 28 82 1 0 29 83 1 0 29 84 1 0 29 85 1 0 30 86 1 0 30 87 1 0 30 88 1 0 31 89 1 0 31 90 1 0 31 91 1 0 32 92 1 0 32 93 1 0 32 94 1 0 34 95 1 1 36 96 1 1 39 97 1 0 40 98 1 6 41 99 1 1 42100 1 6 43101 1 0 44102 1 0 45103 1 0 M END

Standard InCHIKey	NARQRJFIZNOSJV-IIFCQZNRSA-N
Standard InCHI	InChI=1S/C36H58O9/c1-31(2)16-20-19-8-9-22-33(4)12-11-24(44-30-27(41)25(39)26(40)28(45-30)29(42)43)34(5,18-37)21(33)10-13-36(22,7)35(19,6)15-14-32(20,3)23(38)17-31/h8,20-28,30,37-41H,9-18H2,1-7H3,(H,42,43)/t20-,21+,22+,23+,24-,25-,26-,27+,28-,30+,32+,33-,34-,35+,36+/m0/s1
SMILES	OC[C@]1(C)[C@H](CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(C[C@H]1O)(C)C)C)C)C)O[C@@H]1O[C@H](C(=O)O)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	634.41	Volume:	653.712 ? Van der Waals volume.
Dense:	0.97	LogP:	3.115 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.025 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.64 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	33.0
TPSA:	156.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.199	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.431	Fsp³:	0.917
MCE-18:	130.783 ? 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:	0.88	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.03 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.208	Promiscuous compounds:	0.121

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.855	MDCK Permeability:	-5.217
Pgp-inhibitor:	0.0	Pgp-substrate:	0.065
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):	0.0
20% Bioavailability (F20%):	0.062	30% Bioavailability (F30%):	0.006
50% Bioavailability (F50%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026	MRP1:	0.984
Plasma Protein Binding (PPB):	78.35%	Volume Distribution (VD):	-0.558
Fu:	14.746% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.942
OATP1B3 inhibitor:	0.003	BCRP inhibitor:	0.057
BSEP inhibitor:	0.77

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.006	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.018
HLM stability:	0.018 ? 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):

0.716

Half-life (T1/2):

1.886

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.017
Human Hepatotoxicity (H-HT):	0.451	Drug-induced Liver Injury (DILI):	0.613
AMES Toxicity:	0.318	Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.073	Skin Sensitization:	0.988
Carcinogencity:	0.525	Eye Corrosion:	0.0
Eye Irritation:	0.073	Respiratory Toxicity:	0.082
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.928
Hematotoxicity:	0.414	Drug-induced Nephrotoxicity:	0.966
Genotoxicity:	0.513	RPMI-8226 Immunitoxicity:	0.041
A549 Cytotoxicity:	0.074	Hek293 Cytotoxicity:	0.119
BCF:	0.712 ? 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:	3.442 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.002 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.204 ? 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
NPO32725	soybeans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12088420]

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
ED50	6

Activity Type	# Activity
Cell line	1
Non-molecular	5

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
NPT90	Cell line	DU-145	Homo sapiens	ED50	=	9.13	ug ml-1	PMID[21667925]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	9.61	ug ml-1	PMID[12088420]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	9.59	ug ml-1	PMID[12088420]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	8.77	ug ml-1	PMID[12088420]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	28.68	ug ml-1	PMID[12088420]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	37.29	ug ml-1	PMID[12088420]

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 NPC224121 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	19962
0.1-0.2	25507
0.2-0.3	3273
0.3-0.4	777
0.4-0.5	280
0.5-0.6	40
0.6-0.7	9
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	Natural Product ID
0.7419	Intermediate Similarity	NPC118440
0.7188	Intermediate Similarity	NPC236657
0.7113	Intermediate Similarity	NPC218954
0.7065	Intermediate Similarity	NPC473884
0.6742	Remote Similarity	NPC480937
0.6596	Remote Similarity	NPC482748
0.6458	Remote Similarity	NPC475171
0.6429	Remote Similarity	NPC11551
0.6404	Remote Similarity	NPC286347
0.6354	Remote Similarity	NPC157868
0.63	Remote Similarity	NPC611191
0.6224	Remote Similarity	NPC242840
0.6196	Remote Similarity	NPC294112
0.5922	Remote Similarity	NPC95437
0.5865	Remote Similarity	NPC114692
0.5825	Remote Similarity	NPC131469
0.5816	Remote Similarity	NPC309780
0.58	Remote Similarity	NPC482717
0.5789	Remote Similarity	NPC480943
0.5743	Remote Similarity	NPC75417
0.5729	Remote Similarity	NPC480938
0.5714	Remote Similarity	NPC603870
0.5696	Remote Similarity	NPC230295
0.5696	Remote Similarity	NPC98386
0.5673	Remote Similarity	NPC31193
0.5607	Remote Similarity	NPC187618
0.5607	Remote Similarity	NPC120116
0.5543	Remote Similarity	NPC204407
0.5484	Remote Similarity	NPC28198
0.5484	Remote Similarity	NPC476123
0.5405	Remote Similarity	NPC313110
0.5392	Remote Similarity	NPC482751
0.537	Remote Similarity	NPC477191
0.5333	Remote Similarity	NPC251768
0.5333	Remote Similarity	NPC159309
0.5333	Remote Similarity	NPC86222
0.5319	Remote Similarity	NPC57362
0.5263	Remote Similarity	NPC177246
0.5189	Remote Similarity	NPC40775
0.5185	Remote Similarity	NPC64715
0.5185	Remote Similarity	NPC603832
0.5143	Remote Similarity	NPC482741
0.5143	Remote Similarity	NPC482745
0.5143	Remote Similarity	NPC482743
0.5143	Remote Similarity	NPC146753
0.5138	Remote Similarity	NPC114484
0.5096	Remote Similarity	NPC472949
0.5091	Remote Similarity	NPC301449
0.5091	Remote Similarity	NPC601290
0.505	Remote Similarity	NPC270667
0.5047	Remote Similarity	NPC44716
0.5046	Remote Similarity	NPC302887
0.5045	Remote Similarity	NPC477192

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC224121 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6367
0.1-0.2	2718
0.2-0.3	61
0.3-0.4	1
0.4-0.5	3
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