NPASS Compound

Natural Product: NPC204407

Natural Product ID	NPC204407
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Hederagenin-3-O-Beta-D-Glucopyranoside
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL455747
PubChem CID	13518139
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 9.3533 1.5988 2.3010 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2240 1.9693 1.5662 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3683 0.7491 1.3305 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2320 1.0858 0.5982 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6982 -0.0272 -0.0805 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3618 0.2410 -0.2737 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4886 -0.6175 0.3933 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8647 0.0482 1.5924 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4043 0.2232 1.5845 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8121 0.3835 0.1859 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1203 -0.9413 -0.4679 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5563 -1.3449 -0.4931 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1350 -1.3032 -1.8965 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6086 -2.8497 -0.1293 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7718 -3.6000 -0.9057 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4395 -1.0447 -1.8300 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0607 -1.0477 -1.5026 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5130 0.2148 -0.8086 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6794 0.4629 0.3985 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1209 1.6865 1.1025 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5963 1.7082 1.1901 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4702 0.9561 0.5429 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9546 -0.0583 -0.4051 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9866 -1.4725 0.1655 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8824 -0.1326 -1.5779 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8176 1.0260 -1.7217 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7482 1.1459 -0.4968 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9634 1.1530 0.7702 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4858 0.4278 1.9410 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5659 -0.5491 1.7876 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8826 0.0296 2.3549 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4007 -1.8352 2.5811 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9058 -0.9404 0.3756 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8753 0.1811 -0.5860 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4151 2.4833 -0.7589 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2702 3.3937 0.0923 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1634 2.7399 -1.8756 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4358 1.3543 -1.7862 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4549 1.5587 -0.4286 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5326 -0.2488 -1.2827 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9911 -0.1081 -0.8987 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2043 -0.2818 0.6024 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9673 -1.5712 1.0123 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5141 1.1148 -1.3116 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4152 -1.5082 -1.8664 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0722 2.2432 2.1012 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6541 2.7660 2.1034 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5955 2.4221 0.6274 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0587 0.3443 2.2919 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7601 -0.9291 0.5772 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1878 -1.3763 0.8678 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1323 -0.4386 2.5610 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3494 1.0669 1.6752 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9159 -0.6893 2.0160 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1414 1.0498 2.2561 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5697 -1.6740 0.1647 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3812 -1.3689 -2.6998 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8086 -2.1665 -2.0694 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7822 -0.3886 -2.0283 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3225 -2.8800 0.9607 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6740 -3.1310 -0.2552 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0723 -4.0822 -0.3833 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7112 -0.2659 -2.5273 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6128 -2.0930 -2.1813 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6478 -1.3167 -2.3794 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1028 -1.8548 -0.7073 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8722 -0.3769 1.1317 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7554 1.7577 2.1546 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8365 2.6452 0.6169 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0670 2.4433 1.8875 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2978 -1.7124 0.9364 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0157 -1.5473 0.6360 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0791 -2.2189 -0.6685 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4034 -0.3022 -2.5579 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5828 -1.0259 -1.5057 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3594 1.9859 -1.9761 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4983 0.7748 -2.5637 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0121 2.2535 1.0849 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6071 -0.1054 2.4247 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7884 1.1083 2.8034 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8896 -0.0628 3.4460 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0048 1.0489 1.9691 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7134 -0.6170 1.9512 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2468 -1.6137 3.6713 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5713 -2.4554 2.2049 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3708 -2.3824 2.5156 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2921 -1.7779 -0.0136 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9591 -1.3635 0.3352 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8967 0.6703 -0.6016 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8262 -0.2851 -1.6189 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3780 3.6900 -2.2123 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1679 1.2454 -2.6052 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5078 2.3407 -1.2783 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4498 1.3760 -2.3101 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9838 1.3257 -1.4003 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2925 1.9919 0.2018 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7759 2.4262 -0.5515 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2717 0.4768 -2.1120 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6086 -0.8893 -1.3818 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2677 -0.0444 0.7960 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6569 -1.9861 1.5539 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1789 1.0218 -2.0460 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0371 -1.5062 -2.7615 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 30 31 1 0 30 32 1 0 30 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 1 29 79 1 0 29 80 1 0 31 81 1 0 31 82 1 0 31 83 1 0 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 6 42100 1 6 43101 1 0 44102 1 0 45103 1 0 M END

Standard InCHIKey	CCDRPBGPIXPGRW-DLQTVUGOSA-N
Standard InCHI	InChI=1S/C36H58O9/c1-31(2)13-15-36(30(42)43)16-14-34(5)20(21(36)17-31)7-8-24-32(3)11-10-25(33(4,19-38)23(32)9-12-35(24,34)6)45-29-28(41)27(40)26(39)22(18-37)44-29/h7,21-29,37-41H,8-19H2,1-6H3,(H,42,43)/t21-,22+,23+,24+,25-,26+,27-,28+,29-,32-,33-,34+,35+,36-/m0/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]3CC(C)(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:	2.501 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.576 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.121 ? 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:	0.194	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.298	Fsp³:	0.917
MCE-18:	128.058 ? 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:	0.953	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.203	Promiscuous compounds:	0.106

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.92	MDCK Permeability:	-5.239
Pgp-inhibitor:	0.0	Pgp-substrate:	0.001
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):	0.004
20% Bioavailability (F20%):	0.039	30% Bioavailability (F30%):	0.034
50% Bioavailability (F50%):	0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.102	MRP1:	0.601
Plasma Protein Binding (PPB):	81.825%	Volume Distribution (VD):	-0.554
Fu:	12.638% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.491	BCRP inhibitor:	0.008
BSEP inhibitor:	0.541

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.006	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.013	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.015
HLM stability:	0.116 ? 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):

0.889

Half-life (T1/2):

1.762

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.007
Human Hepatotoxicity (H-HT):	0.785	Drug-induced Liver Injury (DILI):	0.868
AMES Toxicity:	0.654	Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.022	Skin Sensitization:	0.999
Carcinogencity:	0.738	Eye Corrosion:	0.0
Eye Irritation:	0.025	Respiratory Toxicity:	0.134
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.97
Hematotoxicity:	0.664	Drug-induced Nephrotoxicity:	0.966
Genotoxicity:	0.461	RPMI-8226 Immunitoxicity:	0.041
A549 Cytotoxicity:	0.189	Hek293 Cytotoxicity:	0.106
BCF:	1.067 ? 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:	3.66 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.33 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.438 ? 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
NPO29483	Swartzia schomburgkii	Species	Fabaceae	Eukaryota	n.a.	suriname rainforest	n.a.	PMID[11087583]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[31301930]
NPO13638	Vernonia brachycalyx	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9170288]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO13638	Vernonia brachycalyx	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29483	Swartzia schomburgkii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13638	Vernonia brachycalyx	Species	Asteraceae	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
IC12	3
IC50	5
ED50	1
Inhibition	1

Activity Type	# Activity
Cell line	5
Organism	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
NPT81	Cell line	A549	Homo sapiens	IC50	=	59000.0	nM	PMID[19200744]
NPT579	Cell line	DLD-1	Homo sapiens	IC50	=	59000.0	nM	PMID[19200744]
NPT81	Cell line	A549	Homo sapiens	IC50	=	65000.0	nM	PMID[19200744]
NPT579	Cell line	DLD-1	Homo sapiens	IC50	=	89000.0	nM	PMID[19200744]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	13400.0	nM	PMID[31301930]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	125.0	ug ml-1	PMID[11087583]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	200.0	ug ml-1	PMID[11087583]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	280.0	ug ml-1	PMID[11087583]
NPT842	Organism	Leishmania mexicana	Leishmania mexicana	ED50	>	50.0	uM	PMID[33479679]
NPT842	Organism	Leishmania mexicana	Leishmania mexicana	Inhibition	>=	95.0	%	PMID[33479679]

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
-	Planorbella trivolvis	LC50	=	30000.0	nM	PMID[22069667]

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 NPC204407 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	19674
0.1-0.2	24323
0.2-0.3	4239
0.3-0.4	993
0.4-0.5	444
0.5-0.6	105
0.6-0.7	47
0.7-0.8	0
0.8-0.85	4
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9054	High Similarity	NPC606107
0.8861	High Similarity	NPC270667
0.8642	High Similarity	NPC136877
0.8313	Intermediate Similarity	NPC59804
0.8193	Intermediate Similarity	NPC12288
0.8077	Intermediate Similarity	NPC28198
0.8077	Intermediate Similarity	NPC476123
0.7952	Intermediate Similarity	NPC164194
0.7848	Intermediate Similarity	NPC57362
0.7667	Intermediate Similarity	NPC139044
0.7586	Intermediate Similarity	NPC127056
0.7586	Intermediate Similarity	NPC109079
0.75	Intermediate Similarity	NPC472949
0.7471	Intermediate Similarity	NPC174679
0.7471	Intermediate Similarity	NPC25605
0.7471	Intermediate Similarity	NPC279554
0.7439	Intermediate Similarity	NPC31839
0.7419	Intermediate Similarity	NPC276093
0.7416	Intermediate Similarity	NPC22956
0.7381	Intermediate Similarity	NPC284807
0.7363	Intermediate Similarity	NPC180550
0.7363	Intermediate Similarity	NPC35405
0.7253	Intermediate Similarity	NPC114304
0.7195	Intermediate Similarity	NPC283849
0.7024	Intermediate Similarity	NPC286347
0.7021	Intermediate Similarity	NPC257468
0.6947	Remote Similarity	NPC79718
0.6941	Remote Similarity	NPC100383
0.6923	Remote Similarity	NPC488561
0.6915	Remote Similarity	NPC471383
0.6832	Remote Similarity	NPC323341
0.6832	Remote Similarity	NPC133818
0.6813	Remote Similarity	NPC114441
0.6804	Remote Similarity	NPC323359
0.6804	Remote Similarity	NPC324875
0.6804	Remote Similarity	NPC292677
0.6782	Remote Similarity	NPC294112
0.6771	Remote Similarity	NPC119794
0.6735	Remote Similarity	NPC488564
0.6705	Remote Similarity	NPC191410
0.6703	Remote Similarity	NPC56713
0.6629	Remote Similarity	NPC475472
0.66	Remote Similarity	NPC62725
0.6591	Remote Similarity	NPC475633
0.6591	Remote Similarity	NPC473538
0.6458	Remote Similarity	NPC104400
0.6458	Remote Similarity	NPC10320
0.6447	Remote Similarity	NPC480946
0.6447	Remote Similarity	NPC130577
0.6447	Remote Similarity	NPC142415
0.6447	Remote Similarity	NPC102683
0.6364	Remote Similarity	NPC270768
0.6364	Remote Similarity	NPC59263
0.6364	Remote Similarity	NPC210106
0.633	Remote Similarity	NPC471385
0.6322	Remote Similarity	NPC177246
0.6316	Remote Similarity	NPC80843
0.6289	Remote Similarity	NPC473383
0.6286	Remote Similarity	NPC166422
0.6286	Remote Similarity	NPC219180
0.6286	Remote Similarity	NPC251263
0.6211	Remote Similarity	NPC6377
0.6211	Remote Similarity	NPC208381
0.6203	Remote Similarity	NPC120840
0.6168	Remote Similarity	NPC54636
0.6154	Remote Similarity	NPC275809
0.6082	Remote Similarity	NPC469945
0.6076	Remote Similarity	NPC158141
0.6076	Remote Similarity	NPC110308
0.6058	Remote Similarity	NPC476992
0.6042	Remote Similarity	NPC473884
0.6	Remote Similarity	NPC242611
0.6	Remote Similarity	NPC298554
0.5922	Remote Similarity	NPC488209
0.5914	Remote Similarity	NPC473481
0.5904	Remote Similarity	NPC96580
0.5876	Remote Similarity	NPC488516
0.5875	Remote Similarity	NPC231063
0.5875	Remote Similarity	NPC282395
0.5851	Remote Similarity	NPC22676
0.5842	Remote Similarity	NPC481082
0.5842	Remote Similarity	NPC73829
0.5842	Remote Similarity	NPC164419
0.575	Remote Similarity	NPC182797
0.575	Remote Similarity	NPC282616
0.575	Remote Similarity	NPC84319
0.575	Remote Similarity	NPC52021
0.575	Remote Similarity	NPC52169
0.575	Remote Similarity	NPC488562
0.575	Remote Similarity	NPC599947
0.5743	Remote Similarity	NPC118440
0.5714	Remote Similarity	NPC475486
0.5714	Remote Similarity	NPC604575
0.5699	Remote Similarity	NPC209894
0.5684	Remote Similarity	NPC127853
0.5679	Remote Similarity	NPC481360
0.567	Remote Similarity	NPC108748
0.566	Remote Similarity	NPC480939
0.5657	Remote Similarity	NPC475171
0.5625	Remote Similarity	NPC198664
0.5607	Remote Similarity	NPC288205
0.5607	Remote Similarity	NPC51465
0.5595	Remote Similarity	NPC296164
0.5579	Remote Similarity	NPC475611
0.5579	Remote Similarity	NPC480938
0.5577	Remote Similarity	NPC114692
0.5556	Remote Similarity	NPC121798
0.5556	Remote Similarity	NPC37038
0.5556	Remote Similarity	NPC234346
0.5543	Remote Similarity	NPC224121
0.5521	Remote Similarity	NPC76999
0.5514	Remote Similarity	NPC280941
0.5514	Remote Similarity	NPC235772
0.549	Remote Similarity	NPC11551
0.5488	Remote Similarity	NPC106112
0.5488	Remote Similarity	NPC261935
0.5481	Remote Similarity	NPC95437
0.5481	Remote Similarity	NPC488515
0.5478	Remote Similarity	NPC161717
0.5455	Remote Similarity	NPC480424
0.5429	Remote Similarity	NPC236657
0.5426	Remote Similarity	NPC256798
0.5422	Remote Similarity	NPC200752
0.5402	Remote Similarity	NPC601365
0.54	Remote Similarity	NPC295371
0.54	Remote Similarity	NPC157868
0.5385	Remote Similarity	NPC274507
0.5385	Remote Similarity	NPC131469
0.5375	Remote Similarity	NPC280654
0.5357	Remote Similarity	NPC474963
0.534	Remote Similarity	NPC40775
0.534	Remote Similarity	NPC159309
0.534	Remote Similarity	NPC86222
0.5327	Remote Similarity	NPC187618
0.5301	Remote Similarity	NPC130278
0.53	Remote Similarity	NPC473373
0.53	Remote Similarity	NPC482748
0.5294	Remote Similarity	NPC192791
0.5294	Remote Similarity	NPC242840
0.5288	Remote Similarity	NPC258885
0.5287	Remote Similarity	NPC474727
0.5258	Remote Similarity	NPC189884
0.5258	Remote Similarity	NPC214484
0.5258	Remote Similarity	NPC51947
0.5258	Remote Similarity	NPC138334
0.5238	Remote Similarity	NPC228784
0.5238	Remote Similarity	NPC324341
0.5238	Remote Similarity	NPC601810
0.5192	Remote Similarity	NPC44716
0.5192	Remote Similarity	NPC251768
0.5185	Remote Similarity	NPC120116
0.5181	Remote Similarity	NPC307282
0.5181	Remote Similarity	NPC64872
0.5181	Remote Similarity	NPC25906
0.5181	Remote Similarity	NPC156981
0.5179	Remote Similarity	NPC471384
0.5169	Remote Similarity	NPC111466
0.5152	Remote Similarity	NPC48499
0.5143	Remote Similarity	NPC475591
0.5143	Remote Similarity	NPC236870
0.5143	Remote Similarity	NPC473405
0.514	Remote Similarity	NPC281148
0.514	Remote Similarity	NPC114484
0.5119	Remote Similarity	NPC472149
0.5119	Remote Similarity	NPC609452
0.5116	Remote Similarity	NPC130520
0.5104	Remote Similarity	NPC471967
0.5102	Remote Similarity	NPC171007
0.5102	Remote Similarity	NPC190849
0.51	Remote Similarity	NPC603870
0.5094	Remote Similarity	NPC475504
0.5093	Remote Similarity	NPC291903
0.5054	Remote Similarity	NPC203974
0.5054	Remote Similarity	NPC237503
0.5051	Remote Similarity	NPC1046
0.505	Remote Similarity	NPC235405
0.505	Remote Similarity	NPC475516
0.5047	Remote Similarity	NPC302887

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC204407 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6354
0.1-0.2	2687
0.2-0.3	96
0.3-0.4	11
0.4-0.5	2
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