NPASS Compound

Natural Product: NPC46388

Natural Product ID	NPC46388
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Pomolic Acid-28-O-Beta-D-Glucopyranosyl Ester
IUPAC Name	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-1,10-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2253394
PubChem CID	76322845
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 9.0118 2.8506 -0.4900 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9496 2.2096 0.1453 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0289 1.5368 -0.8783 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0285 0.9405 -0.1855 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7316 1.3116 -0.4820 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8967 0.5622 0.3681 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9354 -0.3285 -0.0777 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8295 -0.4478 -1.3241 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0561 -1.1204 0.8292 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0073 -1.9710 1.6644 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5657 -3.1278 0.9044 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4540 -3.9466 0.3526 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0920 -3.3253 0.5884 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1212 -1.9257 0.0139 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2429 -1.3626 -0.1593 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9335 -1.7487 -1.2292 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3096 -1.2935 -1.5672 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9016 -0.4693 -0.4787 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8398 0.4590 -0.0120 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8533 -0.4098 0.7892 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2031 0.5106 1.3216 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4336 -0.1602 1.7961 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5310 -1.1696 1.8777 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0542 1.0680 -1.1606 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2689 1.5569 0.8846 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5974 2.1715 0.4772 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5661 1.0301 0.3774 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2229 0.1458 -0.7847 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3209 0.8285 -2.1094 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2456 -0.9990 -0.8061 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2042 -0.9148 0.3425 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9731 0.3896 0.3398 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9608 1.5086 0.4617 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2923 2.6588 -0.4568 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1236 2.0544 1.8953 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7676 0.5141 -0.7994 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1136 -4.2417 -0.1527 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7154 -3.3667 1.9159 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5292 -5.3773 0.8050 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5980 2.7966 -0.2926 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4837 3.4522 -1.3617 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5103 2.5054 -1.8797 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1427 1.8288 -3.0413 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1180 4.5780 -0.8387 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2989 3.2439 -0.5609 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8554 2.7989 0.0322 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3747 1.4256 0.8036 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3812 2.9089 0.7962 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6580 0.7458 -1.3487 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5325 1.1021 -1.5519 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6066 -2.2279 2.6500 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8800 -1.2874 1.8936 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2989 -2.8052 0.1185 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2063 -3.7049 1.6348 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5806 -3.9631 -0.7690 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5350 -2.0420 -1.0286 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4451 -2.4643 -1.9248 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2832 -0.8397 -2.5587 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9094 -2.2442 -1.6903 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1017 -1.1854 0.3780 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2467 1.0492 2.1965 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4872 1.3061 0.6066 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1870 -0.6645 2.7775 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1631 0.6323 2.0832 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7471 -2.2169 1.5142 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4680 -0.6935 2.2565 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8878 -1.3063 2.7724 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0695 0.5775 -1.2927 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8270 2.1490 -0.9739 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5694 1.0162 -2.1297 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5171 2.3922 0.8060 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3201 1.3132 1.9584 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4279 2.7273 -0.4403 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9018 2.9011 1.2551 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3777 0.4016 1.3014 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4216 1.0223 -2.2842 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0521 0.1064 -2.9082 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8322 1.7928 -2.2005 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8499 -0.9988 -1.7371 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7559 -1.9888 -0.7601 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9608 -1.7179 0.1801 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7712 -1.0834 1.3257 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6732 0.3383 1.1994 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4003 3.0996 -0.9445 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7682 3.5233 0.0947 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0846 2.3727 -1.2094 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2044 2.0107 2.1496 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8313 3.1194 1.9445 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4989 1.4542 2.6047 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5478 -0.0861 -0.6590 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1573 -5.2036 0.4449 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4751 -4.5260 -1.1467 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9248 -3.9173 -0.0778 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5952 -4.3222 2.1485 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2135 -5.5382 1.8445 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6010 -5.6768 0.7419 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9931 -6.0691 0.0929 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9839 3.1583 0.6784 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8764 3.7981 -2.2282 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3922 3.1400 -2.1917 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9557 1.2850 -3.2887 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9016 4.7556 -1.4292 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1395 3.3440 -1.5326 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 2 0 9 7 1 6 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 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 20 23 1 1 19 24 1 6 19 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 33 35 1 0 32 36 1 0 13 37 1 0 13 38 1 1 12 39 1 0 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 22 9 1 0 33 27 1 0 14 9 1 0 20 15 1 0 28 18 1 0 1 46 1 0 2 47 1 0 2 48 1 0 3 49 1 6 5 50 1 6 10 51 1 0 10 52 1 0 11 53 1 0 11 54 1 0 12 55 1 6 14 56 1 6 16 57 1 0 17 58 1 0 17 59 1 0 18 60 1 1 21 61 1 0 21 62 1 0 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 23 67 1 0 24 68 1 0 24 69 1 0 24 70 1 0 25 71 1 0 25 72 1 0 26 73 1 0 26 74 1 0 27 75 1 1 29 76 1 0 29 77 1 0 29 78 1 0 30 79 1 0 30 80 1 0 31 81 1 0 31 82 1 0 32 83 1 1 34 84 1 0 34 85 1 0 34 86 1 0 35 87 1 0 35 88 1 0 35 89 1 0 36 90 1 0 37 91 1 0 37 92 1 0 37 93 1 0 38 94 1 0 39 95 1 0 39 96 1 0 39 97 1 0 40 98 1 1 41 99 1 6 42100 1 6 43101 1 0 44102 1 0 45103 1 0 M END

Standard InCHIKey	RRIMLWHUVCZACL-HPUCWRFUSA-N
Standard InCHI	InChI=1S/C36H58O9/c1-19-10-15-36(30(42)45-29-27(41)26(40)25(39)21(18-37)44-29)17-16-33(5)20(28(36)35(19,7)43)8-9-23-32(4)13-12-24(38)31(2,3)22(32)11-14-34(23,33)6/h8,19,21-29,37-41,43H,9-18H2,1-7H3/t19-,21-,22+,23-,24+,25-,26+,27-,28-,29+,32+,33-,34-,35-,36+/m1/s1
SMILES	OC[C@H]1O[C@@H](OC(=O)[C@@]23CC[C@H]([C@@]([C@H]3C3=CC[C@H]4[C@@]([C@@]3(CC2)C)(C)CC[C@@H]2[C@]4(C)CC[C@@H](C2(C)C)O)(C)O)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:	2.472 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.733 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.766 ? 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:	0.202	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.407	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:	0.827	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.045 ? 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:	0.166	Promiscuous compounds:	0.151

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.831	MDCK Permeability:	-5.168
Pgp-inhibitor:	0.0	Pgp-substrate:	0.292
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):	0.187
20% Bioavailability (F20%):	0.944	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.797	MRP1:	0.786
Plasma Protein Binding (PPB):	80.647%	Volume Distribution (VD):	-0.353
Fu:	12.938% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.007
BSEP inhibitor:	0.034

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.117	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.074	CYP3A4-substrate:	0.011
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.306
HLM stability:	0.064 ? 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):

1.573

Half-life (T1/2):

2.356

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.043
Human Hepatotoxicity (H-HT):	0.687	Drug-induced Liver Injury (DILI):	0.482
AMES Toxicity:	0.849	Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.146	Skin Sensitization:	0.999
Carcinogencity:	0.759	Eye Corrosion:	0.0
Eye Irritation:	0.016	Respiratory Toxicity:	0.202
Drug-induced Neurotoxicity:	0.013	Ototoxicity:	0.959
Hematotoxicity:	0.436	Drug-induced Nephrotoxicity:	0.977
Genotoxicity:	0.927	RPMI-8226 Immunitoxicity:	0.111
A549 Cytotoxicity:	0.833	Hek293 Cytotoxicity:	0.495
BCF:	1.301 ? 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:	3.65 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.323 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.539 ? 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
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO26261	Streptomyces tendae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27642865]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36235013]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39409699]
NPO9182	Lychnophora passerina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26048	Grateloupia elliptica	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26261	Streptomyces tendae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24698	Protium unifoliolatum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4318	Aspergillus cristatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26283	Streptomyces djakartensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25339	Trillium smallii	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25649	Calliandra haematocephala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26261	Streptomyces tendae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26345	Sideroxylon tomentosum	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25992	Lasallia papulosa	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24698	Protium unifoliolatum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25765	Dryopteris aemula	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26399	Crepidiastrum lanceolatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4318	Aspergillus cristatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26048	Grateloupia elliptica	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26283	Streptomyces djakartensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28950	Angelonia integerrima	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9182	Lychnophora passerina	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
Inhibition	1
Activity	1

Activity Type	# Activity
Cell line	1
Organism	1

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
NPT993	Cell line	Hepatocyte	Mus musculus	Activity	=	0.1	%	PMID[29353722]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	27.0	%	PMID[17274628]

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 NPC46388 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	20196
0.1-0.2	23659
0.2-0.3	4585
0.3-0.4	1095
0.4-0.5	226
0.5-0.6	70
0.6-0.7	11
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8919	High Similarity	NPC37739
0.8312	Intermediate Similarity	NPC310014
0.8312	Intermediate Similarity	NPC269315
0.7792	Intermediate Similarity	NPC167383
0.7763	Intermediate Similarity	NPC191763
0.775	Intermediate Similarity	NPC271138
0.759	Intermediate Similarity	NPC47063
0.75	Intermediate Similarity	NPC204458
0.75	Intermediate Similarity	NPC189884
0.75	Intermediate Similarity	NPC138334
0.7079	Intermediate Similarity	NPC58448
0.6951	Remote Similarity	NPC237503
0.6848	Remote Similarity	NPC75417
0.6774	Remote Similarity	NPC160415
0.6632	Remote Similarity	NPC68175
0.6588	Remote Similarity	NPC137917
0.6429	Remote Similarity	NPC605954
0.6395	Remote Similarity	NPC7870
0.6395	Remote Similarity	NPC75747
0.6264	Remote Similarity	NPC29069
0.6136	Remote Similarity	NPC110139
0.6136	Remote Similarity	NPC108709
0.5977	Remote Similarity	NPC116794
0.5955	Remote Similarity	NPC102914
0.5922	Remote Similarity	NPC36831
0.5909	Remote Similarity	NPC306746
0.5843	Remote Similarity	NPC68419
0.5824	Remote Similarity	NPC128925
0.5824	Remote Similarity	NPC256798
0.5823	Remote Similarity	NPC259788
0.5823	Remote Similarity	NPC255589
0.5806	Remote Similarity	NPC214484
0.5758	Remote Similarity	NPC104071
0.5714	Remote Similarity	NPC220984
0.5684	Remote Similarity	NPC179434
0.5684	Remote Similarity	NPC48499
0.5638	Remote Similarity	NPC90856
0.5638	Remote Similarity	NPC269095
0.5618	Remote Similarity	NPC190837
0.5591	Remote Similarity	NPC209894
0.5579	Remote Similarity	NPC78046
0.5567	Remote Similarity	NPC235405
0.5567	Remote Similarity	NPC475516
0.5556	Remote Similarity	NPC475171
0.5545	Remote Similarity	NPC473459
0.551	Remote Similarity	NPC249848
0.551	Remote Similarity	NPC107966
0.5455	Remote Similarity	NPC295371
0.5455	Remote Similarity	NPC473884
0.5455	Remote Similarity	NPC39211
0.5455	Remote Similarity	NPC157868
0.5443	Remote Similarity	NPC40552
0.5443	Remote Similarity	NPC246708
0.54	Remote Similarity	NPC469946
0.5385	Remote Similarity	NPC199457
0.5354	Remote Similarity	NPC473373
0.5354	Remote Similarity	NPC150400
0.5347	Remote Similarity	NPC192791
0.5347	Remote Similarity	NPC223301
0.5347	Remote Similarity	NPC242840
0.5347	Remote Similarity	NPC171544
0.5347	Remote Similarity	NPC112352
0.5326	Remote Similarity	NPC604133
0.5294	Remote Similarity	NPC30735
0.5263	Remote Similarity	NPC607754
0.5253	Remote Similarity	NPC139894
0.5248	Remote Similarity	NPC161674
0.5243	Remote Similarity	NPC40775
0.5243	Remote Similarity	NPC10607
0.5243	Remote Similarity	NPC251768
0.5243	Remote Similarity	NPC159309
0.5243	Remote Similarity	NPC102439
0.5243	Remote Similarity	NPC101744
0.5243	Remote Similarity	NPC46665
0.5243	Remote Similarity	NPC86222
0.5217	Remote Similarity	NPC479080
0.5217	Remote Similarity	NPC65590
0.5217	Remote Similarity	NPC125923
0.5192	Remote Similarity	NPC475591
0.5192	Remote Similarity	NPC63159
0.5192	Remote Similarity	NPC236870
0.5192	Remote Similarity	NPC235438
0.5146	Remote Similarity	NPC309714
0.5143	Remote Similarity	NPC222580
0.5143	Remote Similarity	NPC297263
0.5098	Remote Similarity	NPC473343
0.5096	Remote Similarity	NPC11551
0.5096	Remote Similarity	NPC480475
0.5048	Remote Similarity	NPC148417
0.5047	Remote Similarity	NPC281148
0.5047	Remote Similarity	NPC104372
0.5047	Remote Similarity	NPC114484

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC46388 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7394
0.1-0.2	1684
0.2-0.3	68
0.3-0.4	3
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