NPASS Compound

Natural Product: NPC191763

Natural Product ID	NPC191763
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Siaresinolic Acid-28-O-Beta-D-Glucopyranosyl Ester
IUPAC Name	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-1,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2253398
PubChem CID	76330022
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 -2.3224 -4.6058 0.6551 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3126 -3.9866 -0.7137 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3745 -5.1054 -1.7270 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4458 -3.0455 -0.9517 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0845 -1.7821 -1.6754 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0625 -0.9671 -0.8766 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4455 0.1135 -1.7024 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4511 0.8343 -0.7715 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7497 -0.1182 -0.6226 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2868 -0.3414 -1.9823 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2175 -1.3019 0.0891 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8827 -1.8404 1.1013 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1833 -1.3630 1.6435 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7914 -0.4140 0.6768 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1383 0.1132 1.1126 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2060 0.6284 2.5013 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0772 -1.1025 1.0416 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5105 -0.7191 1.1568 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8975 0.2825 0.1192 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0150 1.5018 0.1184 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3682 2.4716 1.2030 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3116 2.2260 -1.2077 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6003 1.0827 0.0657 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6197 2.2346 0.0583 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3649 1.7161 -0.6160 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8070 0.5939 0.2293 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0350 1.2504 1.3612 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2454 0.6031 0.1854 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1073 -1.9244 -0.2504 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9823 -3.2465 -0.9644 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8844 -3.1756 -2.3285 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8665 -0.2897 0.1919 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5686 -0.5396 1.3861 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8914 0.5728 -0.0699 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5910 1.1627 0.9991 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4389 2.6661 1.0264 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1490 3.3652 -0.0841 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1017 2.4132 -0.7438 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7730 1.6104 0.3467 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9210 0.8641 -0.2915 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6948 0.1900 0.6351 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9279 0.7747 1.0234 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1219 3.1961 -1.3315 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2203 3.8547 -0.9841 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9475 3.1101 2.2502 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3127 -4.9537 0.9377 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9653 -5.5258 0.6205 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7571 -3.9624 1.4312 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8275 -6.0215 -1.2944 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3730 -5.3889 -2.1055 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9918 -4.8456 -2.6113 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9292 -2.7446 0.0082 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2556 -3.5356 -1.5429 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0364 -1.1727 -1.7080 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7996 -1.9106 -2.7220 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9857 -0.2048 -2.6341 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2280 0.8598 -1.9290 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1711 1.7819 -1.2295 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9968 0.9324 0.1916 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0871 0.6033 -2.5850 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3898 -0.5568 -2.0388 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8303 -1.1276 -2.5854 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4201 -2.7327 1.5866 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9285 -0.9256 2.6382 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8232 -2.2863 1.7847 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0403 -1.0517 -0.2294 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3117 1.7292 2.5921 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3690 0.3518 3.1706 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1161 0.2313 3.0477 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9274 -1.5926 0.0596 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8367 -1.7774 1.9002 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8352 -0.4168 2.1662 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1008 -1.6560 0.9309 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7506 -0.2057 -0.8887 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3088 2.9981 0.8578 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6531 1.9985 2.1598 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6108 3.2543 1.2775 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0096 3.2792 -1.1655 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4041 2.1727 -1.4212 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7937 1.7413 -2.0523 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4578 0.5513 -0.9242 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0117 3.0361 -0.6355 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4256 2.6747 1.0354 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6278 2.5448 -0.6332 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6832 1.4077 -1.6254 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6715 1.6853 2.1327 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5050 2.1259 0.8800 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3257 0.5587 1.8311 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6543 0.0114 0.8639 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6117 -2.2230 0.7344 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1469 -3.7962 -0.4853 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0451 -3.6188 -2.6309 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1509 0.7934 1.9448 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3495 2.8737 1.0387 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7525 4.2389 0.2934 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6093 1.7943 -1.4936 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2166 2.3194 1.0727 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5892 1.6223 -0.7867 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5908 0.1821 -1.0872 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4370 0.4183 1.5755 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8076 3.6381 -2.1599 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2894 3.3591 -1.8418 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3049 2.9007 3.0002 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 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 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 19 28 1 0 11 29 1 0 29 30 1 0 30 31 1 0 6 32 1 1 32 33 2 0 32 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 37 44 1 0 36 45 1 0 30 2 1 0 42 35 1 0 29 6 1 0 26 9 1 0 26 14 1 0 23 15 1 0 1 46 1 0 1 47 1 0 1 48 1 0 3 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 0 5 55 1 0 7 56 1 0 7 57 1 0 8 58 1 0 8 59 1 0 10 60 1 0 10 61 1 0 10 62 1 0 12 63 1 0 13 64 1 0 13 65 1 0 14 66 1 6 16 67 1 0 16 68 1 0 16 69 1 0 17 70 1 0 17 71 1 0 18 72 1 0 18 73 1 0 19 74 1 6 21 75 1 0 21 76 1 0 21 77 1 0 22 78 1 0 22 79 1 0 22 80 1 0 23 81 1 6 24 82 1 0 24 83 1 0 25 84 1 0 25 85 1 0 27 86 1 0 27 87 1 0 27 88 1 0 28 89 1 0 29 90 1 1 30 91 1 1 31 92 1 0 35 93 1 1 36 94 1 1 37 95 1 1 38 96 1 6 39 97 1 1 40 98 1 0 40 99 1 0 41100 1 0 43101 1 0 44102 1 0 45103 1 0 M END

Standard InCHIKey	BPRNBIVVHNFCPZ-SKCKXSBFSA-N
Standard InCHI	InChI=1S/C36H58O9/c1-31(2)14-16-36(30(43)45-29-27(41)26(40)25(39)20(18-37)44-29)17-15-34(6)19(24(36)28(31)42)8-9-22-33(5)12-11-23(38)32(3,4)21(33)10-13-35(22,34)7/h8,20-29,37-42H,9-18H2,1-7H3/t20-,21+,22-,23+,24-,25-,26+,27-,28+,29+,33+,34-,35-,36+/m1/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]2[C@@H]1O)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	634.41	Volume:	653.712 ? Van der Waals volume.
Dense:	0.97	LogP:	2.623 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.845 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.76 ? 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:	5.346	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:	0.906	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.06 ? 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:	0.161	Promiscuous compounds:	0.073

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.898	MDCK Permeability:	-5.146
Pgp-inhibitor:	0.0	Pgp-substrate:	0.132
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):	0.092
20% Bioavailability (F20%):	0.945	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.95	MRP1:	0.707
Plasma Protein Binding (PPB):	79.032%	Volume Distribution (VD):	-0.26
Fu:	13.961% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.006
BSEP inhibitor:	0.068

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.01	CYP2C19-substrate:	0.02
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.838
HLM stability:	0.611 ? 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):

1.7

Half-life (T1/2):

2.194

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.043
Human Hepatotoxicity (H-HT):	0.674	Drug-induced Liver Injury (DILI):	0.549
AMES Toxicity:	0.899	Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.101	Skin Sensitization:	0.999
Carcinogencity:	0.677	Eye Corrosion:	0.0
Eye Irritation:	0.012	Respiratory Toxicity:	0.155
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.965
Hematotoxicity:	0.593	Drug-induced Nephrotoxicity:	0.955
Genotoxicity:	0.786	RPMI-8226 Immunitoxicity:	0.134
A549 Cytotoxicity:	0.849	Hek293 Cytotoxicity:	0.447
BCF:	1.32 ? 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:	3.72 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.473 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.639 ? 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
EC50	1
Inhibition	5

Activity Type	# Activity
Organism	6

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
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	EC50	=	80.0	ug.mL-1	PMID[17274628]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	7.6	%	PMID[17274628]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	25.3	%	PMID[17274628]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	65.7	%	PMID[17274628]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	84.5	%	PMID[17274628]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	89.2	%	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 NPC191763 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	20801
0.1-0.2	22915
0.2-0.3	4605
0.3-0.4	1176
0.4-0.5	257
0.5-0.6	76
0.6-0.7	16
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
0.8243	Intermediate Similarity	NPC605954
0.7867	Intermediate Similarity	NPC167383
0.7763	Intermediate Similarity	NPC46388
0.7662	Intermediate Similarity	NPC116794
0.7407	Intermediate Similarity	NPC128925
0.7407	Intermediate Similarity	NPC256798
0.7	Intermediate Similarity	NPC237503
0.6914	Remote Similarity	NPC37739
0.6829	Remote Similarity	NPC137917
0.6593	Remote Similarity	NPC161674
0.6477	Remote Similarity	NPC29069
0.6429	Remote Similarity	NPC7870
0.6429	Remote Similarity	NPC310014
0.6429	Remote Similarity	NPC269315
0.6429	Remote Similarity	NPC75747
0.6316	Remote Similarity	NPC148417
0.6163	Remote Similarity	NPC110139
0.6163	Remote Similarity	NPC108709
0.6105	Remote Similarity	NPC104071
0.6047	Remote Similarity	NPC187056
0.6047	Remote Similarity	NPC68419
0.6047	Remote Similarity	NPC606216
0.6047	Remote Similarity	NPC607023
0.5977	Remote Similarity	NPC271138
0.5977	Remote Similarity	NPC102914
0.593	Remote Similarity	NPC306746
0.5909	Remote Similarity	NPC220984
0.5889	Remote Similarity	NPC47063
0.587	Remote Similarity	NPC48499
0.5824	Remote Similarity	NPC204458
0.5824	Remote Similarity	NPC189884
0.5824	Remote Similarity	NPC90856
0.5824	Remote Similarity	NPC214484
0.5824	Remote Similarity	NPC269095
0.5824	Remote Similarity	NPC138334
0.5814	Remote Similarity	NPC190837
0.5761	Remote Similarity	NPC78046
0.5745	Remote Similarity	NPC235405
0.5714	Remote Similarity	NPC473459
0.5699	Remote Similarity	NPC179434
0.5684	Remote Similarity	NPC473373
0.5684	Remote Similarity	NPC249848
0.5684	Remote Similarity	NPC107966
0.5625	Remote Similarity	NPC295371
0.5612	Remote Similarity	NPC30735
0.5604	Remote Similarity	NPC209894
0.5579	Remote Similarity	NPC475516
0.5567	Remote Similarity	NPC475171
0.5556	Remote Similarity	NPC102439
0.5556	Remote Similarity	NPC101744
0.5521	Remote Similarity	NPC58448
0.5464	Remote Similarity	NPC473884
0.5464	Remote Similarity	NPC39211
0.5464	Remote Similarity	NPC157868
0.5455	Remote Similarity	NPC40552
0.5455	Remote Similarity	NPC246708
0.5417	Remote Similarity	NPC139894
0.5408	Remote Similarity	NPC473343
0.5408	Remote Similarity	NPC469946
0.54	Remote Similarity	NPC10607
0.54	Remote Similarity	NPC46665
0.5393	Remote Similarity	NPC65590
0.5393	Remote Similarity	NPC125923
0.5393	Remote Similarity	NPC199457
0.5361	Remote Similarity	NPC150400
0.5354	Remote Similarity	NPC192791
0.5354	Remote Similarity	NPC75417
0.5354	Remote Similarity	NPC223301
0.5354	Remote Similarity	NPC242840
0.5354	Remote Similarity	NPC171544
0.5354	Remote Similarity	NPC112352
0.5347	Remote Similarity	NPC475591
0.5347	Remote Similarity	NPC63159
0.5347	Remote Similarity	NPC236870
0.5347	Remote Similarity	NPC68175
0.5347	Remote Similarity	NPC235438
0.5333	Remote Similarity	NPC604133
0.53	Remote Similarity	NPC109588
0.53	Remote Similarity	NPC160415
0.53	Remote Similarity	NPC309714
0.5269	Remote Similarity	NPC607754
0.5248	Remote Similarity	NPC40775
0.5248	Remote Similarity	NPC251768
0.5248	Remote Similarity	NPC159309
0.5248	Remote Similarity	NPC11551
0.5248	Remote Similarity	NPC480475
0.5248	Remote Similarity	NPC86222
0.5222	Remote Similarity	NPC479080
0.5217	Remote Similarity	NPC136768
0.5192	Remote Similarity	NPC281148
0.5146	Remote Similarity	NPC31193
0.5146	Remote Similarity	NPC222580
0.5146	Remote Similarity	NPC297263
0.5098	Remote Similarity	NPC305267
0.5094	Remote Similarity	NPC80986
0.5088	Remote Similarity	NPC110633
0.5048	Remote Similarity	NPC104372
0.5048	Remote Similarity	NPC114484
0.5047	Remote Similarity	NPC187290

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC191763 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7409
0.1-0.2	1653
0.2-0.3	82
0.3-0.4	5
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