NPASS Compound

Natural Product: NPC163430

Natural Product ID	NPC163430
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DPQCZNIGGNJGTD-MVCBGFDASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	46173943
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

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 112111 0 0 0 0 0 0 0 0999 V2000 14.2406 3.0453 -3.2853 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6109 2.1110 -2.2345 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0822 2.8885 -1.0972 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4744 2.1972 0.0474 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2342 1.4580 -0.1032 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2229 0.3368 -1.0832 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8423 -0.3199 -0.8794 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8570 -1.5940 -0.5240 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5876 -2.3178 -0.3015 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4279 -1.3888 -0.5443 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1150 -2.1591 -0.2800 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9068 -1.2811 -0.5049 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6240 -1.9993 -0.2556 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5613 -2.4943 1.1659 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6562 -1.3386 2.1228 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6212 -1.7308 3.5559 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4188 -2.4652 4.0250 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1397 -1.7627 3.8701 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0980 -2.1832 4.4772 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9300 -0.6316 3.0930 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3363 -0.0109 2.9993 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3287 1.4661 3.1534 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8080 -0.2987 1.5560 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7391 -1.7898 1.3010 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0662 0.2381 1.3327 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3425 1.2318 0.4160 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4149 1.7005 -0.2816 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7337 1.7557 0.2485 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3337 1.1855 -0.9859 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7361 1.7007 -1.1598 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6208 1.3154 0.0079 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7004 -0.1644 0.1691 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2593 -0.8264 -1.0394 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6885 -0.3122 -1.2764 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2627 -0.9792 -2.4715 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3500 -1.7114 -2.4248 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1776 -1.9984 -1.2308 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.6020 -1.5645 -1.4329 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8218 -0.1167 -1.6906 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3949 0.7888 -0.5794 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.6736 2.2445 -0.9508 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2521 3.1811 0.1615 C 0 0 0 0 0 0 0 0 0 0 0 0 14.6235 3.9584 -2.8124 H 0 0 0 0 0 0 0 0 0 0 0 0 14.9980 2.4723 -3.8185 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4370 3.2964 -3.9995 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9143 1.5040 -2.7699 H 0 0 0 0 0 0 0 0 0 0 0 0 14.4498 1.4386 -1.8917 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3731 3.6880 -1.5229 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9278 3.5517 -0.7107 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2561 1.4532 0.4412 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3216 2.9456 0.9162 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3588 2.1297 -0.4032 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9174 1.0230 0.8966 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0960 0.7095 -2.1394 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9627 -0.4261 -0.9445 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9588 0.2523 -1.0241 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8134 -2.1241 -0.3945 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5286 -3.1183 -1.0786 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5513 -2.7766 0.7062 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4540 -0.5750 0.2078 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4164 -0.9520 -1.5394 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1638 -2.5837 0.7401 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0449 -3.0082 -1.0050 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0428 -0.3431 0.0755 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9362 -0.9081 -1.5845 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7311 -1.3998 -0.5186 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6454 -2.9263 -0.8970 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5769 -3.0356 1.3272 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4040 -3.1832 1.3268 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8946 -0.5484 1.8517 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6413 -0.8062 1.9726 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7006 -0.8003 4.1824 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5160 -2.3570 3.7573 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3704 -3.5177 3.6439 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5555 -2.5992 5.1414 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1141 -0.4944 3.6242 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0888 1.9752 2.2477 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4049 1.7742 3.3125 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2093 1.8640 4.0114 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0543 0.1818 0.9052 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2995 -2.1138 1.3932 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3643 -2.2555 2.0942 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0942 -1.9817 0.2914 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7623 2.8460 0.2891 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3343 1.3912 1.1275 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3030 0.0746 -0.9570 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7232 1.4893 -1.8612 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1235 1.3317 -2.1186 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6769 2.8093 -1.1657 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6327 1.7238 -0.1607 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2546 1.8363 0.9228 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4102 -0.3735 1.0147 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7372 -0.6223 0.4861 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2827 -1.9379 -0.9249 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6139 -0.6347 -1.9139 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5900 0.7720 -1.5804 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2684 -0.3532 -0.3727 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7741 -0.8698 -3.4615 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6832 -2.1637 -3.3851 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1276 -3.1226 -1.0839 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8045 -1.5742 -0.2913 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2344 -1.8316 -0.5386 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0500 -2.1687 -2.2707 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.9154 0.0936 -1.8902 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3107 0.2430 -2.6194 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3435 0.6548 -0.3443 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9656 0.5667 0.3566 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0925 2.4514 -1.8699 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7475 2.3799 -1.1643 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1519 3.4777 0.7539 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4939 2.6742 0.8226 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7486 4.0466 -0.3065 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 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 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 21 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 26 27 2 0 26 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 1 0 34 35 1 0 35 36 2 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 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 2 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 0 5 53 1 0 6 54 1 0 6 55 1 0 7 56 1 0 8 57 1 0 9 58 1 0 9 59 1 0 10 60 1 0 10 61 1 0 11 62 1 0 11 63 1 0 12 64 1 0 12 65 1 0 13 66 1 0 13 67 1 0 14 68 1 0 14 69 1 0 15 70 1 0 15 71 1 0 16 72 1 0 16 73 1 0 17 74 1 0 17 75 1 0 21 76 1 1 22 77 1 0 22 78 1 0 22 79 1 0 23 80 1 6 24 81 1 0 24 82 1 0 24 83 1 0 28 84 1 0 28 85 1 0 29 86 1 0 29 87 1 0 30 88 1 0 30 89 1 0 31 90 1 0 31 91 1 0 32 92 1 0 32 93 1 0 33 94 1 0 33 95 1 0 34 96 1 0 34 97 1 0 35 98 1 0 36 99 1 0 37100 1 0 37101 1 0 38102 1 0 38103 1 0 39104 1 0 39105 1 0 40106 1 0 40107 1 0 41108 1 0 41109 1 0 42110 1 0 42111 1 0 42112 1 0 M END

Standard InCHIKey	DPQCZNIGGNJGTD-MVCBGFDASA-N
Standard InCHI	InChI=1S/C38H70O4/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-38(40)42-36(4)35(3)41-37(39)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2/h15-18,35-36H,5-14,19-34H2,1-4H3/b17-15+,18-16-/t35-,36+/m1/s1
SMILES	CCCCCC/C=C/CCCCCCCCCC(=O)O[C@@H](C)[C@@H](C)OC(=O)CCCCCCC/C=CCCCCCC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	590.53	Volume:	690.419 ? Van der Waals volume.
Dense:	0.855	LogP:	11.216 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.105 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-10.85 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	33.0	Rigid Bonds:	4.0
TPSA:	52.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	0.0	Rings:	0.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.046	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.322	Fsp³:	0.842
MCE-18:	4.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.65	Fluc inhibitor:	0.273 ? 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:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.905	Promiscuous compounds:	0.563

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.049	MDCK Permeability:	-4.726
Pgp-inhibitor:	0.973	Pgp-substrate:	0.0
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):	0.012
20% Bioavailability (F20%):	0.957	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.994
Plasma Protein Binding (PPB):	99.509%	Volume Distribution (VD):	-0.267
Fu:	0.12% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.002
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.717
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.996
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.354 ? 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):

4.901

Half-life (T1/2):

1.077

ADMET: Toxicity

hERG Blockers:	0.642	hERG Blockers (10um):	0.88
Human Hepatotoxicity (H-HT):	0.591	Drug-induced Liver Injury (DILI):	0.001
AMES Toxicity:	0.022	Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.298	Skin Sensitization:	1.0
Carcinogencity:	0.011	Eye Corrosion:	0.959
Eye Irritation:	0.969	Respiratory Toxicity:	0.836
Drug-induced Neurotoxicity:	0.01	Ototoxicity:	0.185
Hematotoxicity:	0.008	Drug-induced Nephrotoxicity:	0.739
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.163
A549 Cytotoxicity:	0.975	Hek293 Cytotoxicity:	0.513
BCF:	-0.346 ? 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:	4.617 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.792 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.049 ? 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
NPO4232	Rabdosia coetsoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12126.1	Coix lacryma- jobi var. ma - yuen	Varieties	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12126	Coix lacryma-jobi	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12126	Coix lacryma-jobi	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4232	Rabdosia coetsoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12126.1	Coix lacryma- jobi var. ma - yuen	Varieties	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12126	Coix lacryma-jobi	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4232	Rabdosia coetsoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12126	Coix lacryma-jobi	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4232	Rabdosia coetsoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12126	Coix lacryma-jobi	Species	Poaceae	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 NPC163430 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	23495
0.1-0.2	23089
0.2-0.3	2718
0.3-0.4	413
0.4-0.5	97
0.5-0.6	23
0.6-0.7	12
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	Natural Product ID
0.7059	Intermediate Similarity	NPC148192
0.7	Intermediate Similarity	NPC309606
0.6562	Remote Similarity	NPC128061
0.6364	Remote Similarity	NPC39633
0.6216	Remote Similarity	NPC476660
0.6207	Remote Similarity	NPC47363
0.6207	Remote Similarity	NPC287231
0.6154	Remote Similarity	NPC54925
0.6061	Remote Similarity	NPC228473
0.6	Remote Similarity	NPC48218
0.6	Remote Similarity	NPC141481
0.6	Remote Similarity	NPC464342
0.6	Remote Similarity	NPC223677
0.6	Remote Similarity	NPC28779
0.5806	Remote Similarity	NPC603863
0.5789	Remote Similarity	NPC81896
0.5789	Remote Similarity	NPC476657
0.5789	Remote Similarity	NPC476659
0.5676	Remote Similarity	NPC277597
0.5581	Remote Similarity	NPC473559
0.5581	Remote Similarity	NPC324981
0.5526	Remote Similarity	NPC104537
0.5429	Remote Similarity	NPC139545
0.5294	Remote Similarity	NPC23155
0.525	Remote Similarity	NPC475443
0.525	Remote Similarity	NPC473829
0.525	Remote Similarity	NPC476658
0.5161	Remote Similarity	NPC63182
0.5161	Remote Similarity	NPC145045
0.5161	Remote Similarity	NPC52700
0.5135	Remote Similarity	NPC10316
0.5135	Remote Similarity	NPC200845
0.5128	Remote Similarity	NPC481557
0.5128	Remote Similarity	NPC481560
0.5122	Remote Similarity	NPC330426
0.5122	Remote Similarity	NPC127091
0.5122	Remote Similarity	NPC22101

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC163430 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6957
0.1-0.2	2040
0.2-0.3	118
0.3-0.4	27
0.4-0.5	6
0.5-0.6	0
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
0.6207	Remote Similarity	NPD2699	Pre-clinical

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