NPASS Compound

Natural Product: NPC76902

Natural Product ID	NPC76902
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WQLVFSAGQJTQCK-YVOQUZMQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 72 77 0 0 0 0 0 0 0 0999 V2000 7.6392 1.2367 0.0044 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1630 0.9102 -0.0385 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8024 0.1849 -1.3054 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7144 -0.8229 -1.1367 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8681 -0.4374 0.0356 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7376 -1.4648 0.2450 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1021 -2.4414 1.3321 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6511 -0.5497 0.5525 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9523 0.4856 -0.5640 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8628 1.4459 -0.3714 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2270 0.6473 0.2520 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5414 0.6431 -0.4041 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9985 2.0262 -0.6928 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4497 2.1743 -0.8700 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3080 1.2544 -0.5098 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7574 1.5107 -0.7367 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4318 1.3297 0.6265 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2378 -0.1196 1.0037 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7854 -0.3808 1.2967 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8969 -0.0229 0.1094 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1185 -1.0970 -0.9569 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4945 -0.0126 0.6082 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0421 -1.3491 1.0538 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5728 -1.4908 1.2797 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2651 -0.8201 0.2537 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0022 -1.4665 -1.0808 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7554 1.7061 0.6071 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2184 0.7961 -0.2143 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5465 -0.3558 1.2213 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8694 -0.0137 1.1203 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8195 2.3128 0.2263 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1723 0.6617 0.8094 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1498 0.9546 -0.9380 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5356 1.8223 0.1071 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7096 -0.3518 -1.6620 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5582 0.9666 -2.0654 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0944 -1.8360 -1.0130 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0541 -0.7462 -2.0485 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6141 -1.9654 -0.7118 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5384 -2.2930 2.2655 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8648 -3.4679 0.9534 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1970 -2.4096 1.4777 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7576 0.0024 1.4952 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9653 -0.0285 -1.5494 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5220 1.8790 -1.3411 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1793 2.2738 0.3206 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3556 0.9578 1.3186 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6280 0.0409 -1.3270 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5319 2.3274 -1.6780 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5772 2.7783 0.0280 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7892 3.1195 -1.3318 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9466 2.5177 -1.1463 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2297 0.7881 -1.4088 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8673 1.9842 1.3318 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6153 -0.7604 0.1738 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8030 -0.3138 1.9263 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5062 0.1725 2.2083 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6605 -1.4548 1.5000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0046 -0.8372 -1.5932 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2596 -1.1354 -1.6676 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3443 -2.0795 -0.5016 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4681 0.6732 1.4960 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5390 -1.5545 2.0490 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3787 -2.1918 0.4058 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3470 -2.5792 1.3897 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3139 -1.0503 2.2854 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0387 -1.8973 -1.1019 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1221 -0.8074 -1.9387 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6726 -2.3344 -1.2085 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7811 2.6874 0.4702 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5452 -0.8930 1.1148 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1363 0.5614 2.0475 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 17 27 1 0 9 28 1 0 5 29 1 1 29 30 1 0 30 2 1 0 28 5 1 0 25 8 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 1 3 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 6 39 1 6 7 40 1 0 7 41 1 0 7 42 1 0 8 43 1 1 9 44 1 6 10 45 1 0 10 46 1 0 11 47 1 1 12 48 1 6 13 49 1 0 13 50 1 0 14 51 1 0 16 52 1 0 16 53 1 0 17 54 1 1 18 55 1 0 18 56 1 0 19 57 1 0 19 58 1 0 21 59 1 0 21 60 1 0 21 61 1 0 22 62 1 1 23 63 1 0 23 64 1 0 24 65 1 0 24 66 1 0 26 67 1 0 26 68 1 0 26 69 1 0 27 70 1 0 30 71 1 0 30 72 1 0 M END

Standard InCHIKey	WQLVFSAGQJTQCK-YVOQUZMQSA-N
Standard InCHI	InChI=1S/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17-,19-,20+,21-,22-,23+,24-,25-,26-,27+/m0/s1
SMILES	C[C@H]1CC[C@@]2([C@@H](C)[C@H]3[C@@H](C[C@H]4[C@@H]5CC=C6C[C@H](CC[C@]6(C)[C@H]5CC[C@]34C)O)O2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	414.31	Volume:	447.944 ? Van der Waals volume.
Dense:	0.925	LogP:	4.942 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.211 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.308 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	30.0
TPSA:	38.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.516	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.244	Fsp³:	0.926
MCE-18:	137.077 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.852	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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.212	Promiscuous compounds:	0.422

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.123	MDCK Permeability:	-4.937
Pgp-inhibitor:	0.568	Pgp-substrate:	0.525
PAMPA:	0.036 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.008	30% Bioavailability (F30%):	0.146
50% Bioavailability (F50%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055	MRP1:	0.273
Plasma Protein Binding (PPB):	83.843%	Volume Distribution (VD):	0.001
Fu:	15.201% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.995
BSEP inhibitor:	0.973

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	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:	0.017
CYP3A4-inhibitor:	0.945	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.899
HLM stability:	0.685 ? 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):

16.153

Half-life (T1/2):

1.364

ADMET: Toxicity

hERG Blockers:	0.157	hERG Blockers (10um):	0.364
Human Hepatotoxicity (H-HT):	0.561	Drug-induced Liver Injury (DILI):	0.602
AMES Toxicity:	0.237	Rat Oral Acute Toxicity:	0.236
Maximum Recommended Daily Dose:	0.745	Skin Sensitization:	0.987
Carcinogencity:	0.826	Eye Corrosion:	0.084
Eye Irritation:	0.68	Respiratory Toxicity:	0.234
Drug-induced Neurotoxicity:	0.059	Ototoxicity:	0.544
Hematotoxicity:	0.103	Drug-induced Nephrotoxicity:	0.33
Genotoxicity:	0.015	RPMI-8226 Immunitoxicity:	0.111
A549 Cytotoxicity:	0.298	Hek293 Cytotoxicity:	0.719
BCF:	2.396 ? 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:	3.777 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.69 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.455 ? 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
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO15684	Cochliobolus heterostrophus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395513]
NPO7093	Oncorhynchus keta	Species	Salmonidae	Eukaryota	eggs	Pacific	n.a.	PMID[10654418]
NPO7093	Oncorhynchus keta	Species	Salmonidae	Eukaryota	Eggs	n.a.	n.a.	PMID[10654418]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO958	Tambja ceutae	Species	Polyceridae	Eukaryota	n.a.	Azorean	n.a.	PMID[20227875]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36838931]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37480748]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9433811]
NPO4350	Chlorella pyrenoidosa	Species	Chlorellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6107	Acacia lemmoni	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3023	Achillea pratensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3913	Alcea nudiflora	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6722	Anaphalis margaritacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1977	Arum montanum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4050	Boronia lanceolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16714	Campanula pendula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7161	Capparis angulata	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9099	Carissa spinarum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO798	Chloranthus holostegius	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3528	Cinnamomum pedunculatum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10450	Clerodendrum infortunatum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15684	Cochliobolus heterostrophus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4125	Corydalis crystallina	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6951	Dictyota spinulosa	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27244	Dysosma pleiantha	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3456	Eucalyptus campanulata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1814	Euphorbia cattimandoo	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7377	Hemiphragma heterophyllum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7640	Klaseopsis chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4847	Lasianthus wallichii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO586	Lomandra hastilis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO518	Mercurialis leiocarpa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6421	Neolitsea sericea	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4204	Ochradenus baccatus	Species	Resedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7093	Oncorhynchus keta	Species	Salmonidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4411	Plantago ovata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6345	Podocarpus sellowii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1659	Primula denticulata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4773	Pteromys volans	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5739	Rubus foliolosus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6523	Streptococcus pneumoniae	Species	Streptococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO958	Tambja ceutae	Species	Polyceridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO241	Teucrium cossonii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5518	Thuja dolabrata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1244	Trimusculus conica	Species	Trimusculidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2339	Turnera ulmifolia	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5809	Xanthoparmelia tinctina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7093	Oncorhynchus keta	Species	Salmonidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	Leaves	n.a.		Database[FooDB]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27244	Dysosma pleiantha	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7377	Hemiphragma heterophyllum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6421	Neolitsea sericea	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6722	Anaphalis margaritacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4847	Lasianthus wallichii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4773	Pteromys volans	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7377	Hemiphragma heterophyllum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27244	Dysosma pleiantha	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4847	Lasianthus wallichii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6421	Neolitsea sericea	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6722	Anaphalis margaritacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4773	Pteromys volans	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6722	Anaphalis margaritacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9099	Carissa spinarum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6523	Streptococcus pneumoniae	Species	Streptococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2339	Turnera ulmifolia	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27244	Dysosma pleiantha	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6722	Anaphalis margaritacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4847	Lasianthus wallichii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1244	Trimusculus conica	Species	Trimusculidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4050	Boronia lanceolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15684	Cochliobolus heterostrophus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1659	Primula denticulata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4411	Plantago ovata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO798	Chloranthus holostegius	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7093	Oncorhynchus keta	Species	Salmonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16714	Campanula pendula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4350	Chlorella pyrenoidosa	Species	Chlorellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6107	Acacia lemmoni	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5739	Rubus foliolosus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10450	Clerodendrum infortunatum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO241	Teucrium cossonii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5809	Xanthoparmelia tinctina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3528	Cinnamomum pedunculatum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6951	Dictyota spinulosa	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6421	Neolitsea sericea	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1814	Euphorbia cattimandoo	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3456	Eucalyptus campanulata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7640	Klaseopsis chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4773	Pteromys volans	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3913	Alcea nudiflora	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7377	Hemiphragma heterophyllum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO586	Lomandra hastilis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5518	Thuja dolabrata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1977	Arum montanum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO518	Mercurialis leiocarpa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3023	Achillea pratensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4125	Corydalis crystallina	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4204	Ochradenus baccatus	Species	Resedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7161	Capparis angulata	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6345	Podocarpus sellowii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO958	Tambja ceutae	Species	Polyceridae	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

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

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 NPC76902 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	21513
0.1-0.2	25039
0.2-0.3	2853
0.3-0.4	249
0.4-0.5	117
0.5-0.6	66
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC235126
1.0	High Similarity	NPC242419
0.875	High Similarity	NPC486119
0.75	Intermediate Similarity	NPC177818
0.7143	Intermediate Similarity	NPC100451
0.6709	Remote Similarity	NPC181845
0.6324	Remote Similarity	NPC248944
0.6324	Remote Similarity	NPC7479
0.6324	Remote Similarity	NPC257296
0.6232	Remote Similarity	NPC296734
0.6133	Remote Similarity	NPC176406
0.6047	Remote Similarity	NPC306131
0.6047	Remote Similarity	NPC200802
0.6023	Remote Similarity	NPC470432
0.6023	Remote Similarity	NPC230507
0.5972	Remote Similarity	NPC187159
0.5946	Remote Similarity	NPC309493
0.5889	Remote Similarity	NPC113044
0.5889	Remote Similarity	NPC283829
0.5889	Remote Similarity	NPC14704
0.5889	Remote Similarity	NPC161676
0.5778	Remote Similarity	NPC70204
0.5699	Remote Similarity	NPC470433
0.5699	Remote Similarity	NPC46190
0.5699	Remote Similarity	NPC171073
0.5699	Remote Similarity	NPC602423
0.5658	Remote Similarity	NPC147835
0.5658	Remote Similarity	NPC253645
0.5658	Remote Similarity	NPC85001
0.5658	Remote Similarity	NPC95920
0.5638	Remote Similarity	NPC477809
0.5634	Remote Similarity	NPC227260
0.5579	Remote Similarity	NPC300557
0.5556	Remote Similarity	NPC273290
0.5556	Remote Similarity	NPC232044
0.5521	Remote Similarity	NPC480555
0.5521	Remote Similarity	NPC150372
0.5465	Remote Similarity	NPC13190
0.5443	Remote Similarity	NPC482599
0.5373	Remote Similarity	NPC221758
0.5354	Remote Similarity	NPC269297
0.5354	Remote Similarity	NPC222202
0.5333	Remote Similarity	NPC305808
0.5333	Remote Similarity	NPC481427
0.5306	Remote Similarity	NPC294129
0.53	Remote Similarity	NPC475333
0.53	Remote Similarity	NPC224098
0.53	Remote Similarity	NPC208383
0.5278	Remote Similarity	NPC243985
0.5278	Remote Similarity	NPC473943
0.5278	Remote Similarity	NPC280710
0.5256	Remote Similarity	NPC474022
0.525	Remote Similarity	NPC212874
0.5244	Remote Similarity	NPC144790
0.5244	Remote Similarity	NPC149400
0.5244	Remote Similarity	NPC88962
0.5224	Remote Similarity	NPC162742
0.5224	Remote Similarity	NPC304309
0.5224	Remote Similarity	NPC470228
0.5217	Remote Similarity	NPC134847
0.5196	Remote Similarity	NPC480554
0.5181	Remote Similarity	NPC277715
0.5155	Remote Similarity	NPC248746
0.5149	Remote Similarity	NPC32361
0.5147	Remote Similarity	NPC22105
0.5147	Remote Similarity	NPC34019
0.5147	Remote Similarity	NPC107059
0.5147	Remote Similarity	NPC600590
0.5143	Remote Similarity	NPC51014
0.5139	Remote Similarity	NPC603646
0.5102	Remote Similarity	NPC6806
0.5096	Remote Similarity	NPC480553
0.5096	Remote Similarity	NPC477811
0.5072	Remote Similarity	NPC136188
0.5072	Remote Similarity	NPC28657
0.5072	Remote Similarity	NPC474216
0.5072	Remote Similarity	NPC328313
0.5072	Remote Similarity	NPC154330
0.507	Remote Similarity	NPC328714
0.5068	Remote Similarity	NPC24556
0.5068	Remote Similarity	NPC240650

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC76902 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7143
0.1-0.2	1858
0.2-0.3	133
0.3-0.4	8
0.4-0.5	4
0.5-0.6	2
0.6-0.7	1
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
0.6324	Remote Similarity	NPD6928	Phase 2
0.5373	Remote Similarity	NPD4786	Phase 1
0.5072	Remote Similarity	NPD6942	Phase 4

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