NPASS Compound

Natural Product: NPC141481

Natural Product ID	NPC141481
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Diolein
IUPAC Name	[(2S)-3-hydroxy-2-[(E)-octadec-9-enoyl]oxypropyl] (E)-octadec-9-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL57517
PubChem CID	6505653
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000175] Glycerolipids [CHEMONTID:0003809] Diradylglycerols [CHEMONTID:0001129] Diacylglycerols [CHEMONTID:0001644] 1,2-diacylglycerols

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 116115 0 0 0 0 0 0 0 0999 V2000 13.0068 1.2998 1.2068 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4634 0.6675 2.4939 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5381 1.6617 3.1785 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3788 2.0270 2.3162 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4925 0.8210 1.9580 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9242 0.2760 3.1996 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1212 -0.9562 3.1736 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9324 -0.9835 2.2854 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2766 -0.9621 0.8596 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8924 -2.0320 0.1110 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2093 -2.0694 -1.3113 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9201 -2.1620 -2.1281 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1857 -3.3954 -1.7471 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9805 -3.6618 -2.5361 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8036 -2.8020 -2.5555 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8844 -1.3882 -2.9839 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4109 -0.8989 -3.0370 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8418 -1.0397 -1.6908 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4625 -0.6130 -0.7016 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3804 -1.6497 -1.5713 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0386 -1.8203 -0.3443 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3396 -0.4082 0.1560 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0993 0.2462 -0.9006 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6466 1.4285 -1.4228 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5690 1.9173 -0.9299 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2825 2.1756 -2.4962 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4980 1.4273 -2.9955 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1450 2.1639 -4.1574 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6008 3.5300 -3.8724 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6201 3.7963 -2.8391 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9668 3.2427 -2.9659 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2757 1.8202 -2.9603 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0411 1.0344 -1.7292 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6177 1.5123 -0.5789 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4420 0.5502 0.5556 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3670 1.0478 1.6593 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7867 1.1215 1.2164 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3690 -0.1788 0.7756 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3648 -1.2105 1.8591 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1538 -0.7662 3.0658 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1375 -1.8655 4.1276 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7605 -2.2125 4.5916 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2400 -0.4476 1.3636 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3897 -1.1729 1.0714 O 0 0 0 0 0 0 0 0 0 0 0 0 13.7530 0.5910 0.7999 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1998 1.5770 0.5169 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5823 2.1903 1.5643 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3350 0.4548 3.1262 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9717 -0.2662 2.2307 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2578 1.3916 4.1961 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1665 2.5974 3.2725 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7009 2.6925 2.9154 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6616 2.5813 1.4184 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6294 1.3566 1.4235 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9399 0.1512 1.2412 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3396 1.1416 3.6908 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7573 0.0802 3.9705 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8461 -1.2958 4.2286 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8470 -1.8091 2.8856 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3571 -0.0205 2.5268 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2356 -1.8265 2.5288 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7874 -0.2080 0.3125 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3712 -2.8132 0.6194 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7636 -1.1343 -1.6135 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8639 -2.9575 -1.5256 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3979 -1.2196 -1.9980 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2700 -2.1921 -3.2013 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9122 -4.2567 -1.7817 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9177 -3.3404 -0.6364 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 -3.8785 -3.6390 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5927 -4.7141 -2.2469 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4041 -2.7842 -1.4721 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0039 -3.3339 -3.1652 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2907 -0.7405 -2.1424 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3569 -1.1917 -3.9461 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8575 -1.4816 -3.7685 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4172 0.1734 -3.3394 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0055 -2.3304 -0.4690 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3885 -2.2839 0.4366 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4461 0.1758 0.3921 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 3.2001 -2.1539 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5807 2.3163 -3.3452 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1926 1.1609 -2.1956 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1056 0.4909 -3.4380 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8640 1.4633 -4.6129 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2603 2.2905 -4.8908 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6702 4.1129 -3.5492 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8787 4.0995 -4.8163 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7688 4.9506 -2.8836 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1331 3.7175 -1.8210 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5125 3.7635 -3.8444 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5687 3.6997 -2.0915 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4344 1.7682 -3.0698 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9735 1.2466 -3.8670 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2456 -0.0594 -1.8018 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4291 2.5504 -0.4581 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6264 -0.4632 0.2398 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 0.7342 0.9438 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2855 0.4254 2.5636 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0475 2.0591 1.9626 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3719 1.5726 2.0678 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9438 1.8452 0.3822 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8150 -0.5998 -0.0834 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4226 -0.0081 0.4350 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3187 -1.4286 2.1554 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8775 -2.1250 1.4504 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6316 0.1003 3.4966 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1984 -0.5082 2.8085 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6248 -2.7787 3.6684 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7927 -1.5903 4.9805 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7500 -2.5220 5.6721 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0474 -1.3599 4.4827 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3536 -3.0461 3.9515 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5753 0.5934 1.6075 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7394 -0.9138 2.2411 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8168 -0.9049 0.2095 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 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 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 41 42 1 0 22 43 1 0 43 44 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 0 2 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 6 56 1 0 6 57 1 0 7 58 1 0 7 59 1 0 8 60 1 0 8 61 1 0 9 62 1 0 10 63 1 0 11 64 1 0 11 65 1 0 12 66 1 0 12 67 1 0 13 68 1 0 13 69 1 0 14 70 1 0 14 71 1 0 15 72 1 0 15 73 1 0 16 74 1 0 16 75 1 0 17 76 1 0 17 77 1 0 21 78 1 0 21 79 1 0 22 80 1 1 26 81 1 0 26 82 1 0 27 83 1 0 27 84 1 0 28 85 1 0 28 86 1 0 29 87 1 0 29 88 1 0 30 89 1 0 30 90 1 0 31 91 1 0 31 92 1 0 32 93 1 0 32 94 1 0 33 95 1 0 34 96 1 0 35 97 1 0 35 98 1 0 36 99 1 0 36100 1 0 37101 1 0 37102 1 0 38103 1 0 38104 1 0 39105 1 0 39106 1 0 40107 1 0 40108 1 0 41109 1 0 41110 1 0 42111 1 0 42112 1 0 42113 1 0 43114 1 0 43115 1 0 44116 1 0 M END

Standard InCHIKey	AFSHUZFNMVJNKX-BIJVAZSDSA-N
Standard InCHI	InChI=1S/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37,40H,3-16,21-36H2,1-2H3/b19-17+,20-18+/t37-/m0/s1
SMILES	CCCCCCCC/C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC/C=C/CCCCCCCC)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	620.54	Volume:	716.505 ? Van der Waals volume.
Dense:	0.866	LogP:	10.823 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.843 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.418 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	36.0	Rigid Bonds:	4.0
TPSA:	72.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.044	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.219	Fsp³:	0.846
MCE-18:	3.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.643	Fluc inhibitor:	0.294 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.81	Promiscuous compounds:	0.89

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.121	MDCK Permeability:	-4.672
Pgp-inhibitor:	0.613	Pgp-substrate:	0.002
PAMPA:	0.0 ? 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):	0.002
20% Bioavailability (F20%):	0.97	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.408
Plasma Protein Binding (PPB):	99.869%	Volume Distribution (VD):	-0.388
Fu:	0.056% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.005
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.822
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.999
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.295 ? 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):

4.287

Half-life (T1/2):

1.403

ADMET: Toxicity

hERG Blockers:	0.185	hERG Blockers (10um):	0.568
Human Hepatotoxicity (H-HT):	0.863	Drug-induced Liver Injury (DILI):	0.034
AMES Toxicity:	0.12	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.18	Skin Sensitization:	1.0
Carcinogencity:	0.161	Eye Corrosion:	0.006
Eye Irritation:	0.491	Respiratory Toxicity:	0.697
Drug-induced Neurotoxicity:	0.054	Ototoxicity:	0.369
Hematotoxicity:	0.031	Drug-induced Nephrotoxicity:	0.912
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.241
A549 Cytotoxicity:	0.979	Hek293 Cytotoxicity:	0.467
BCF:	-0.499 ? 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:	4.628 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.122 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.448 ? 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
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1246/bcsj.30.618]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309313]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17716892]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO29381	Trichilia rubescens	Species	Meliaceae	Eukaryota	leaves	Kibale National Park, Uganda	2000-2001	PMID[19299148]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[25211032]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466882]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31117521]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31873014]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29363	Aconitum nevadense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28784	Alseodaphne corneri	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27269	Annona impressivenia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29510	Aulacocephalus temmincki	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28971	Bersama yangambiensis	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29189	Castanopsis sclerophylla	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29400	Conocephalum japonicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26192	Cordylanthus kingii	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25981	Crinipellis scabella	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29127	Cystophora scalaris	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29047	Disynaphia halimifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4244	Doodia picta	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28845	Eragrostis viscosa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1245	Eunicella cavolinii	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28824	Forsteronia refracta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3340	Fridericia chica	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28898	Grewia mollis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29203	Gymnocarpium robertianum	Species	Cystopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29154	Heliotropium floridum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28937	Heterotheca grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29415	Hovenia acerba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29142	Kaunia saltensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13818	Narcissus concolor	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29225	Oncoba echinata	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28918	Ophiolepis superba	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29068	Papilio phorcas	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29344	Parabenzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3744	Polycephalomyces nipponicus	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9157	Rubrivivax gelatinosus	Species	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29242	Salvia dorrii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29488	Sophora angustifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29446	Stevia polycephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29292	Teucrium depressum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28805	Thymus piperella	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29381	Trichilia rubescens	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29344	Parabenzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28805	Thymus piperella	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29242	Salvia dorrii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29225	Oncoba echinata	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29363	Aconitum nevadense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26192	Cordylanthus kingii	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27269	Annona impressivenia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29415	Hovenia acerba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29203	Gymnocarpium robertianum	Species	Cystopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3340	Fridericia chica	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1245	Eunicella cavolinii	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29127	Cystophora scalaris	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29381	Trichilia rubescens	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28898	Grewia mollis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29400	Conocephalum japonicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29446	Stevia polycephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28918	Ophiolepis superba	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29047	Disynaphia halimifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28971	Bersama yangambiensis	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13818	Narcissus concolor	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28784	Alseodaphne corneri	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4244	Doodia picta	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29142	Kaunia saltensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28805	Thymus piperella	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28937	Heterotheca grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28845	Eragrostis viscosa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28824	Forsteronia refracta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29510	Aulacocephalus temmincki	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29154	Heliotropium floridum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29292	Teucrium depressum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29189	Castanopsis sclerophylla	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25981	Crinipellis scabella	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3744	Polycephalomyces nipponicus	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9157	Rubrivivax gelatinosus	Species	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29488	Sophora angustifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29344	Parabenzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO29068	Papilio phorcas	Species	Papilionidae	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
Ki	2

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT182	Individual protein	Protein kinase C alpha	Homo sapiens	Ki	=	87.2	nM	PMID[10762046]
NPT4629	Individual protein	Protein kinase C alpha	Bos taurus	Ki	=	87.2	nM	PMID[11384235]

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 NPC141481 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	15931
0.1-0.2	29669
0.2-0.3	3682
0.3-0.4	465
0.4-0.5	62
0.5-0.6	31
0.6-0.7	8
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC48218
1.0	High Similarity	NPC464342
0.925	High Similarity	NPC473559
0.925	High Similarity	NPC324981
0.7	Intermediate Similarity	NPC148192
0.6829	Remote Similarity	NPC104537
0.6591	Remote Similarity	NPC54925
0.6364	Remote Similarity	NPC330426
0.6364	Remote Similarity	NPC127091
0.6364	Remote Similarity	NPC22101
0.6279	Remote Similarity	NPC476660
0.619	Remote Similarity	NPC277597
0.6154	Remote Similarity	NPC128061
0.5909	Remote Similarity	NPC81896
0.5909	Remote Similarity	NPC476657
0.5909	Remote Similarity	NPC476659
0.5893	Remote Similarity	NPC488689
0.5778	Remote Similarity	NPC321919
0.5778	Remote Similarity	NPC475443
0.5778	Remote Similarity	NPC473829
0.5778	Remote Similarity	NPC476654
0.5778	Remote Similarity	NPC476655
0.5778	Remote Similarity	NPC476656
0.5714	Remote Similarity	NPC489083
0.5714	Remote Similarity	NPC223677
0.5714	Remote Similarity	NPC28779
0.5652	Remote Similarity	NPC271921
0.561	Remote Similarity	NPC55678
0.5593	Remote Similarity	NPC21693
0.55	Remote Similarity	NPC23155
0.5435	Remote Similarity	NPC476658
0.541	Remote Similarity	NPC156089
0.541	Remote Similarity	NPC39290
0.5366	Remote Similarity	NPC488257
0.5366	Remote Similarity	NPC469937
0.5366	Remote Similarity	NPC94699
0.5366	Remote Similarity	NPC320588
0.5366	Remote Similarity	NPC53463
0.5319	Remote Similarity	NPC209327
0.525	Remote Similarity	NPC309606
0.5208	Remote Similarity	NPC273508
0.5122	Remote Similarity	NPC26253
0.5094	Remote Similarity	NPC474321
0.5082	Remote Similarity	NPC236649

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC141481 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5943
0.1-0.2	3017
0.2-0.3	160
0.3-0.4	19
0.4-0.5	8
0.5-0.6	1
0.6-0.7	0
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8378	Intermediate Similarity	NPD3730	Pre-clinical
0.7381	Intermediate Similarity	NPD3728	Approved
0.561	Remote Similarity	NPD6125	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