NPASS Compound

Natural Product: NPC57362

Natural Product ID	NPC57362
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-Glucopyranosyl)-23-Hydroxyursolic Acid
IUPAC Name	(1S,2R,4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL461104
PubChem CID	21589723
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 6.8567 4.0273 1.3445 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5124 3.3386 0.3109 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4858 1.8570 0.7055 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2277 1.4556 0.8259 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8066 0.2161 0.4272 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5101 0.3330 -0.0798 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5243 -0.2446 0.7195 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7597 0.8857 1.3254 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3158 0.9797 1.1088 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7510 0.3069 -0.1236 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2829 -1.0892 -0.0779 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7683 -1.2289 -0.0627 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2931 -1.3959 -1.4813 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9979 -2.6118 0.5902 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5116 -2.4911 1.9149 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6274 -1.9044 -1.1572 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7946 -2.1519 -0.6666 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4672 -0.8231 -0.6344 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7421 0.2637 0.0667 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4509 1.5545 -0.1654 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9084 1.3593 -0.3444 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5825 0.2247 -0.2230 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7899 -0.9920 0.1340 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5914 -1.0726 1.6068 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5147 -2.1998 -0.3700 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8861 -2.3055 0.2001 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6968 -1.0439 0.1724 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0781 0.1470 -0.4446 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6958 1.4581 -0.0745 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8247 2.3184 -1.3588 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0888 1.4026 0.4728 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3375 2.7825 1.1512 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2663 0.3059 1.4430 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0919 -0.6273 1.6010 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9670 -1.3860 -0.5145 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2360 -0.8573 -1.6096 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8383 -2.2839 0.0620 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8506 -0.4729 -2.0696 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1812 1.0980 -1.3137 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6226 -0.5183 -0.5553 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0866 -0.3960 -0.1994 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3982 1.0741 -0.1843 C 0 0 2 0 0 0 0 0 0 0 0 0 9.7444 1.2169 0.1580 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7964 -0.9590 -1.2845 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3312 -1.8847 -0.4809 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9031 3.5012 2.2056 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9837 3.4316 -0.6365 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5869 3.6187 0.2707 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9724 1.8461 1.7292 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7297 -0.3827 1.3632 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1084 -0.7108 1.5705 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2133 1.8876 1.0511 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9024 0.8951 2.4523 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9782 2.0490 1.0460 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7094 0.5782 1.9773 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9105 -1.5086 0.9071 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8840 -2.3244 -1.6203 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4792 -1.4797 -2.2360 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9950 -0.5533 -1.7538 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3925 -3.3845 0.1094 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0739 -2.8480 0.6465 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1096 -2.9281 2.5538 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1534 -2.8107 -1.4374 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4791 -1.2967 -2.0991 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7052 -2.6405 0.3185 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3265 -2.7929 -1.3959 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8821 0.0552 1.1758 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2992 2.2282 0.7110 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1130 2.0667 -1.1124 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5387 2.2420 -0.6103 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6751 -0.0721 2.0774 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4081 -1.6688 2.1141 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6667 -1.6318 1.9195 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9384 -3.0946 0.0116 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5469 -2.3078 -1.4507 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9217 -2.6980 1.2451 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3802 -3.1413 -0.3848 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2662 0.0320 -1.5627 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0778 2.0220 0.6703 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2643 1.8633 -2.1996 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8897 2.3308 -1.7141 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5744 3.3638 -1.1406 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8610 1.4165 -0.3422 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3497 3.5606 0.3562 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5427 3.0142 1.8599 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3487 2.7846 1.6102 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4003 0.7733 2.4672 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1939 -0.2714 1.1946 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2628 -0.1437 2.1139 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4686 -1.5311 2.1367 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6532 -2.6619 -0.4199 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4156 -1.1899 -2.7936 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9481 -0.5330 -2.2278 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5687 0.5344 -2.3704 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7988 0.7163 -2.2844 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9065 2.1522 -1.2344 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2862 1.1027 -1.4467 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4952 -0.1889 -1.6069 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3635 -0.9346 0.7045 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2926 1.4490 -1.2236 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3278 1.1425 -0.6572 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2981 -0.7408 -2.1310 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4612 -2.3493 -1.3413 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 6 12 14 1 0 14 15 1 0 11 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 1 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 27 35 1 6 35 36 2 0 35 37 1 0 18 38 1 6 10 39 1 6 5 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 42 3 1 0 12 7 1 0 23 18 1 0 34 27 1 0 19 10 1 0 28 22 1 0 1 46 1 0 2 47 1 0 2 48 1 0 3 49 1 1 5 50 1 1 7 51 1 1 8 52 1 0 8 53 1 0 9 54 1 0 9 55 1 0 11 56 1 1 13 57 1 0 13 58 1 0 13 59 1 0 14 60 1 0 14 61 1 0 15 62 1 0 16 63 1 0 16 64 1 0 17 65 1 0 17 66 1 0 19 67 1 1 20 68 1 0 20 69 1 0 21 70 1 0 24 71 1 0 24 72 1 0 24 73 1 0 25 74 1 0 25 75 1 0 26 76 1 0 26 77 1 0 28 78 1 6 29 79 1 1 30 80 1 0 30 81 1 0 30 82 1 0 31 83 1 6 32 84 1 0 32 85 1 0 32 86 1 0 33 87 1 0 33 88 1 0 34 89 1 0 34 90 1 0 37 91 1 0 38 92 1 0 38 93 1 0 38 94 1 0 39 95 1 0 39 96 1 0 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	SHSTYRBKXWDVCB-CWVWMCCNSA-N
Standard InCHI	InChI=1S/C36H58O9/c1-19-9-14-36(31(42)43)16-15-34(5)21(26(36)20(19)2)7-8-24-32(3)12-11-25(33(4,18-38)23(32)10-13-35(24,34)6)45-30-29(41)28(40)27(39)22(17-37)44-30/h7,19-20,22-30,37-41H,8-18H2,1-6H3,(H,42,43)/t19-,20+,22-,23-,24-,25+,26+,27-,28+,29-,30+,32+,33+,34-,35-,36+/m1/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H]([C@]2(C)CO)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3[C@@H](C)[C@H](C)CC2)C(=O)O)C)C)[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:	2.619 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.826 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.308 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	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:	0.195	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.383	Fsp³:	0.917
MCE-18:	125.333 ? 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:	0.905	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.036 ? 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:	0.175	Promiscuous compounds:	0.089

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.91	MDCK Permeability:	-5.196
Pgp-inhibitor:	0.002	Pgp-substrate:	0.007
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):	0.007
20% Bioavailability (F20%):	0.103	30% Bioavailability (F30%):	0.173
50% Bioavailability (F50%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.269	MRP1:	0.581
Plasma Protein Binding (PPB):	78.539%	Volume Distribution (VD):	-0.589
Fu:	16.045% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.528	BCRP inhibitor:	0.094
BSEP inhibitor:	0.597

ADMET: Metabolism

CYP1A2-inhibitor:	0.021	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:	0.123	CYP3A4-substrate:	0.004
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? 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):

0.809

Half-life (T1/2):

1.782

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.006
Human Hepatotoxicity (H-HT):	0.752	Drug-induced Liver Injury (DILI):	0.889
AMES Toxicity:	0.692	Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.02	Skin Sensitization:	0.999
Carcinogencity:	0.755	Eye Corrosion:	0.0
Eye Irritation:	0.044	Respiratory Toxicity:	0.166
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.967
Hematotoxicity:	0.751	Drug-induced Nephrotoxicity:	0.967
Genotoxicity:	0.521	RPMI-8226 Immunitoxicity:	0.037
A549 Cytotoxicity:	0.249	Hek293 Cytotoxicity:	0.135
BCF:	0.802 ? 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:	3.431 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.902 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.123 ? 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
NPO24490	Cussonia bancoensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510614]
NPO24490	Cussonia bancoensis	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[21443171]
NPO24490	Cussonia bancoensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24490	Cussonia bancoensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24490	Cussonia bancoensis	Species	Araliaceae	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
Cell line	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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	22100.0	nM	PMID[19555125]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	126000.0	nM	PMID[26200131]

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 NPC57362 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	20006
0.1-0.2	23843
0.2-0.3	4376
0.3-0.4	1055
0.4-0.5	445
0.5-0.6	91
0.6-0.7	22
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8101	Intermediate Similarity	NPC177246
0.7848	Intermediate Similarity	NPC204407
0.7326	Intermediate Similarity	NPC473481
0.7108	Intermediate Similarity	NPC606107
0.7045	Intermediate Similarity	NPC270667
0.7	Intermediate Similarity	NPC108748
0.6889	Remote Similarity	NPC136877
0.663	Remote Similarity	NPC59804
0.6588	Remote Similarity	NPC274507
0.6522	Remote Similarity	NPC12288
0.6495	Remote Similarity	NPC258885
0.6494	Remote Similarity	NPC51700
0.6494	Remote Similarity	NPC88716
0.6494	Remote Similarity	NPC68160
0.641	Remote Similarity	NPC61543
0.641	Remote Similarity	NPC293048
0.641	Remote Similarity	NPC225585
0.6322	Remote Similarity	NPC28198
0.6322	Remote Similarity	NPC476123
0.6304	Remote Similarity	NPC164194
0.625	Remote Similarity	NPC485589
0.618	Remote Similarity	NPC31839
0.6162	Remote Similarity	NPC139044
0.6125	Remote Similarity	NPC173089
0.6082	Remote Similarity	NPC475171
0.6071	Remote Similarity	NPC230151
0.6042	Remote Similarity	NPC127056
0.6042	Remote Similarity	NPC109079
0.598	Remote Similarity	NPC276093
0.5979	Remote Similarity	NPC472949
0.5957	Remote Similarity	NPC211798
0.5952	Remote Similarity	NPC485586
0.5952	Remote Similarity	NPC485588
0.5938	Remote Similarity	NPC174679
0.5938	Remote Similarity	NPC25605
0.5938	Remote Similarity	NPC279554
0.5926	Remote Similarity	NPC32407
0.5926	Remote Similarity	NPC263548
0.5926	Remote Similarity	NPC606320
0.5918	Remote Similarity	NPC22956
0.59	Remote Similarity	NPC180550
0.59	Remote Similarity	NPC35405
0.5806	Remote Similarity	NPC284807
0.5802	Remote Similarity	NPC71074
0.5802	Remote Similarity	NPC605937
0.58	Remote Similarity	NPC114304
0.5795	Remote Similarity	NPC484195
0.575	Remote Similarity	NPC274330
0.5732	Remote Similarity	NPC87095
0.5657	Remote Similarity	NPC473884
0.5631	Remote Similarity	NPC257468
0.5625	Remote Similarity	NPC274050
0.5625	Remote Similarity	NPC162632
0.5618	Remote Similarity	NPC485585
0.5604	Remote Similarity	NPC283849
0.5588	Remote Similarity	NPC473383
0.5577	Remote Similarity	NPC79718
0.5566	Remote Similarity	NPC488564
0.5545	Remote Similarity	NPC323341
0.5545	Remote Similarity	NPC133818
0.5542	Remote Similarity	NPC477288
0.5534	Remote Similarity	NPC471383
0.5534	Remote Similarity	NPC118440
0.5532	Remote Similarity	NPC256798
0.5524	Remote Similarity	NPC114692
0.55	Remote Similarity	NPC488561
0.5484	Remote Similarity	NPC286347
0.5474	Remote Similarity	NPC475633
0.5474	Remote Similarity	NPC473538
0.5472	Remote Similarity	NPC323359
0.5472	Remote Similarity	NPC324875
0.5472	Remote Similarity	NPC292677
0.5437	Remote Similarity	NPC11551
0.5435	Remote Similarity	NPC485882
0.5429	Remote Similarity	NPC95437
0.5429	Remote Similarity	NPC119794
0.5426	Remote Similarity	NPC100383
0.5412	Remote Similarity	NPC127689
0.54	Remote Similarity	NPC114441
0.5366	Remote Similarity	NPC477289
0.5361	Remote Similarity	NPC51947
0.5357	Remote Similarity	NPC305464
0.5357	Remote Similarity	NPC19376
0.5357	Remote Similarity	NPC25848
0.5333	Remote Similarity	NPC131469
0.5321	Remote Similarity	NPC62725
0.5319	Remote Similarity	NPC224121
0.5312	Remote Similarity	NPC294112
0.5312	Remote Similarity	NPC209894
0.53	Remote Similarity	NPC56713
0.5294	Remote Similarity	NPC80843
0.5278	Remote Similarity	NPC187618
0.5263	Remote Similarity	NPC485587
0.5258	Remote Similarity	NPC191410
0.5248	Remote Similarity	NPC473373
0.5248	Remote Similarity	NPC178093
0.5248	Remote Similarity	NPC482748
0.5234	Remote Similarity	NPC236657
0.5208	Remote Similarity	NPC173569
0.5204	Remote Similarity	NPC189884
0.5204	Remote Similarity	NPC138334
0.5204	Remote Similarity	NPC30397
0.5204	Remote Similarity	NPC475472
0.5169	Remote Similarity	NPC471385
0.5146	Remote Similarity	NPC479745
0.5143	Remote Similarity	NPC104400
0.5143	Remote Similarity	NPC10320
0.5133	Remote Similarity	NPC471384
0.5106	Remote Similarity	NPC88744
0.51	Remote Similarity	NPC235841
0.51	Remote Similarity	NPC297208
0.5088	Remote Similarity	NPC166422
0.5088	Remote Similarity	NPC219180
0.5088	Remote Similarity	NPC251263
0.5059	Remote Similarity	NPC37221
0.5052	Remote Similarity	NPC471967
0.505	Remote Similarity	NPC603870
0.5049	Remote Similarity	NPC295371
0.5049	Remote Similarity	NPC157868

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC57362 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6406
0.1-0.2	2637
0.2-0.3	94
0.3-0.4	13
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