NPASS Compound

Natural Product: NPC488623

Natural Product ID	NPC488623
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HCNICOLIANUASN-LUVUIASKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44575651
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

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 114116 0 0 0 0 0 0 0 0999 V2000 -13.7929 -2.5877 1.1436 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7552 -2.0273 0.1676 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6218 -1.5070 1.0026 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5657 -0.9311 0.1140 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0247 -1.9610 -0.8237 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9456 -1.3783 -1.7274 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7834 -0.8505 -0.9306 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7339 -0.3046 -1.8613 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2145 0.8211 -2.7124 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0992 1.3196 -3.5882 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9245 1.8275 -2.8060 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3619 2.9700 -1.9271 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2753 3.5747 -1.1272 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5535 2.6927 -0.1627 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4284 1.9820 0.8034 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6335 0.7535 1.1634 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6709 0.6322 0.0270 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2425 0.4316 0.4757 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6832 1.6056 1.1998 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7373 1.3205 1.6142 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6738 1.0517 0.4712 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0513 0.7991 1.0732 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1068 0.5231 0.0425 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8971 1.7228 -0.3428 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6338 2.3892 0.7642 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6544 1.5647 1.4664 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7828 1.0727 0.5859 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7259 0.2516 1.4528 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8629 -0.2294 0.5942 C 0 0 2 0 0 0 0 0 0 0 0 0 10.7949 -1.0439 1.4509 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9714 -1.5550 0.6530 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2142 -1.3545 -0.6157 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4582 -2.0214 -1.0007 C 0 0 2 0 0 0 0 0 0 0 0 0 13.1129 -3.1038 -2.0109 C 0 0 0 0 0 0 0 0 0 0 0 0 13.9335 -2.6414 0.1546 O 0 0 0 0 0 0 0 0 0 0 0 0 13.0504 -2.3748 1.1802 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1445 -2.7699 2.3914 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5736 0.9071 0.1833 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8640 -0.4953 0.5678 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0028 -1.2210 1.4003 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3669 -2.3014 0.5235 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7265 -1.8903 2.5237 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0274 -0.3570 1.8243 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1209 -0.7067 1.2811 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8115 1.7294 -0.7718 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3712 4.2110 -1.9801 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.0290 -1.7533 1.8489 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3274 -3.4543 1.6544 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.6822 -2.8728 0.5431 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4515 -2.8571 -0.4893 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2569 -1.2022 -0.4063 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9719 -0.7781 1.7600 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1993 -2.3724 1.5550 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7926 -0.4911 0.7712 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9534 -0.0940 -0.5216 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7954 -2.3582 -1.5099 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5471 -2.7891 -0.2554 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5893 -2.1754 -2.3947 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3670 -0.5282 -2.3239 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0945 -0.0229 -0.2472 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3284 -1.6284 -0.2832 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3893 -1.1128 -2.5676 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8395 -0.0712 -1.2495 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7392 1.6275 -2.1815 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9883 0.3831 -3.4089 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8252 0.5348 -4.3191 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4971 2.1778 -4.1785 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3892 1.0192 -2.2706 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2086 2.2655 -3.5575 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7056 3.7715 -2.6520 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2799 2.7394 -1.3436 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7082 4.4196 -0.5048 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8648 3.3385 0.4514 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6272 2.5772 1.7258 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3865 1.6206 0.3509 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3067 -0.1503 1.2330 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1438 0.9431 2.1390 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9485 -0.2767 -0.5687 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6440 0.2525 -0.4368 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6467 2.4947 0.5316 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2377 1.8087 2.1560 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7834 0.4671 2.3535 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1106 2.2122 2.1895 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3622 0.2440 -0.1895 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7654 1.9797 -0.1379 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3032 1.6482 1.7358 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6045 0.1503 -0.8780 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6798 1.3648 -1.0770 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2786 2.4279 -0.9360 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1619 3.2768 0.3093 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9758 2.8318 1.5393 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1101 2.2376 2.2530 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1847 0.7516 2.0293 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3696 1.8911 0.1559 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3498 0.3889 -0.1655 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1763 -0.6101 1.8870 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1214 0.8583 2.2914 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4527 -0.7991 -0.2456 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2088 -0.4716 2.2951 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2399 -1.9571 1.7777 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5839 -0.7739 -1.2977 H 0 0 0 0 0 0 0 0 0 0 0 0 14.2054 -1.3109 -1.4388 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2750 -4.1198 -1.5801 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0683 -3.0578 -2.3297 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7351 -2.9831 -2.9404 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6602 1.5511 0.9301 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6325 -2.8821 1.0971 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8361 -1.8190 -0.3499 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1282 -2.9752 0.0813 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4628 -2.9628 2.5803 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8127 -1.8239 2.3577 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4101 -1.4037 3.4791 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3582 -0.4417 2.2007 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6825 4.1494 -2.9336 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 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 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 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 2 0 32 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 36 37 2 0 29 38 1 0 23 39 1 0 39 40 1 0 40 41 1 0 40 42 1 0 40 43 1 0 18 44 1 0 17 45 1 0 13 46 1 0 45 14 1 0 43 22 1 0 36 31 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 0 2 51 1 0 3 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 5 56 1 0 5 57 1 0 6 58 1 0 6 59 1 0 7 60 1 0 7 61 1 0 8 62 1 0 8 63 1 0 9 64 1 0 9 65 1 0 10 66 1 0 10 67 1 0 11 68 1 0 11 69 1 0 12 70 1 0 12 71 1 0 13 72 1 1 14 73 1 1 15 74 1 0 15 75 1 0 16 76 1 0 16 77 1 0 17 78 1 6 18 79 1 6 19 80 1 0 19 81 1 0 20 82 1 0 20 83 1 0 21 84 1 0 21 85 1 0 22 86 1 1 23 87 1 6 24 88 1 0 24 89 1 0 25 90 1 0 25 91 1 0 26 92 1 0 26 93 1 0 27 94 1 0 27 95 1 0 28 96 1 0 28 97 1 0 29 98 1 6 30 99 1 0 30100 1 0 32101 1 0 33102 1 6 34103 1 0 34104 1 0 34105 1 0 38106 1 0 41107 1 0 41108 1 0 41109 1 0 42110 1 0 42111 1 0 42112 1 0 44113 1 0 46114 1 0 M END

Standard InCHIKey	HCNICOLIANUASN-LUVUIASKSA-N
Standard InCHI	InChI=1S/C38H68O8/c1-5-6-7-8-9-10-11-12-13-16-20-31(40)33-24-25-34(44-33)32(41)21-18-23-36-35(45-38(3,4)46-36)22-17-14-15-19-30(39)27-29-26-28(2)43-37(29)42/h26,28,30-36,39-41H,5-25,27H2,1-4H3/t28-,30+,31-,32+,33+,34+,35+,36+/m0/s1
SMILES	CCCCCCCCCCCC[C@@H]([C@H]1CC[C@H]([C@@H](CCC[C@@H]2[C@@H](CCCCC[C@H](CC3=C[C@H](C)OC3=O)O)OC(C)(C)O2)O)O1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	652.49	Volume:	705.183 ? Van der Waals volume.
Dense:	0.925	LogP:	5.427 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.033 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.28 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	25.0	Rigid Bonds:	16.0
TPSA:	114.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.068	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.939	Fsp³:	0.921
MCE-18:	48.822 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.844	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.037 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.512	Promiscuous compounds:	0.317

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.192	MDCK Permeability:	-4.822
Pgp-inhibitor:	0.017	Pgp-substrate:	0.919
PAMPA:	0.031 ? 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):	0.013
20% Bioavailability (F20%):	0.962	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.963
Plasma Protein Binding (PPB):	96.082%	Volume Distribution (VD):	0.419
Fu:	4.055% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.419
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.884
BSEP inhibitor:	0.903

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.033	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.012	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.964
HLM stability:	0.01 ? 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):

5.779

Half-life (T1/2):

0.984

ADMET: Toxicity

hERG Blockers:	0.454	hERG Blockers (10um):	0.801
Human Hepatotoxicity (H-HT):	0.696	Drug-induced Liver Injury (DILI):	0.387
AMES Toxicity:	0.459	Rat Oral Acute Toxicity:	0.205
Maximum Recommended Daily Dose:	0.849	Skin Sensitization:	1.0
Carcinogencity:	0.603	Eye Corrosion:	0.036
Eye Irritation:	0.641	Respiratory Toxicity:	0.926
Drug-induced Neurotoxicity:	0.15	Ototoxicity:	0.628
Hematotoxicity:	0.119	Drug-induced Nephrotoxicity:	0.845
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.077
A549 Cytotoxicity:	0.959	Hek293 Cytotoxicity:	0.513
BCF:	1.205 ? 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:	5.07 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.259 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.262 ? 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
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473425]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975482]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7494150]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673926]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673935]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673936]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[8946744]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8991944]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[9584396]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26234	Annona muricata	Species	Annonaceae	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
ED50	3

Activity Type	# Activity
Cell line	3

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
NPT81	Cell line	A549	Homo sapiens	ED50	=	1.58	10'-4 ug/ml	PMID[7673926]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	2.78	10'-4 ug/ml	PMID[7673926]
NPT139	Cell line	HT-29	Homo sapiens	ED50	>	1.0	ug ml-1	PMID[7673926]

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
-	Artemia	LC50	=	0.131	ug.mL-1	PMID[7673926]

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 NPC488623 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	18160
0.1-0.2	29561
0.2-0.3	1851
0.3-0.4	61
0.4-0.5	30
0.5-0.6	50
0.6-0.7	71
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC488624
1.0	High Similarity	NPC488629
0.7959	Intermediate Similarity	NPC606043
0.7857	Intermediate Similarity	NPC488630
0.7857	Intermediate Similarity	NPC488625
0.7857	Intermediate Similarity	NPC488626
0.78	Intermediate Similarity	NPC107986
0.78	Intermediate Similarity	NPC223871
0.78	Intermediate Similarity	NPC231009
0.78	Intermediate Similarity	NPC103284
0.78	Intermediate Similarity	NPC110710
0.78	Intermediate Similarity	NPC1083
0.78	Intermediate Similarity	NPC82795
0.78	Intermediate Similarity	NPC286338
0.78	Intermediate Similarity	NPC603931
0.78	Intermediate Similarity	NPC604237
0.7647	Intermediate Similarity	NPC488253
0.7647	Intermediate Similarity	NPC473669
0.7647	Intermediate Similarity	NPC488251
0.75	Intermediate Similarity	NPC81045
0.75	Intermediate Similarity	NPC232555
0.75	Intermediate Similarity	NPC39754
0.75	Intermediate Similarity	NPC171135
0.75	Intermediate Similarity	NPC171174
0.75	Intermediate Similarity	NPC182383
0.75	Intermediate Similarity	NPC114694
0.75	Intermediate Similarity	NPC61257
0.75	Intermediate Similarity	NPC320569
0.75	Intermediate Similarity	NPC485248
0.75	Intermediate Similarity	NPC133730
0.75	Intermediate Similarity	NPC191929
0.75	Intermediate Similarity	NPC142117
0.75	Intermediate Similarity	NPC100454
0.75	Intermediate Similarity	NPC242364
0.75	Intermediate Similarity	NPC480249
0.75	Intermediate Similarity	NPC172821
0.75	Intermediate Similarity	NPC485249
0.75	Intermediate Similarity	NPC274446
0.75	Intermediate Similarity	NPC485251
0.75	Intermediate Similarity	NPC151403
0.75	Intermediate Similarity	NPC240695
0.75	Intermediate Similarity	NPC261952
0.75	Intermediate Similarity	NPC605171
0.7358	Intermediate Similarity	NPC93794
0.7358	Intermediate Similarity	NPC488632
0.7358	Intermediate Similarity	NPC134865
0.7358	Intermediate Similarity	NPC473504
0.7358	Intermediate Similarity	NPC103523
0.7358	Intermediate Similarity	NPC81778
0.7358	Intermediate Similarity	NPC40066
0.7358	Intermediate Similarity	NPC488627
0.7358	Intermediate Similarity	NPC488631
0.7273	Intermediate Similarity	NPC20621
0.7273	Intermediate Similarity	NPC318963
0.7273	Intermediate Similarity	NPC602738
0.7273	Intermediate Similarity	NPC605101
0.7222	Intermediate Similarity	NPC280621
0.7222	Intermediate Similarity	NPC48338
0.7222	Intermediate Similarity	NPC488628
0.7091	Intermediate Similarity	NPC178215
0.7091	Intermediate Similarity	NPC42598
0.7091	Intermediate Similarity	NPC473687
0.7091	Intermediate Similarity	NPC204686
0.7091	Intermediate Similarity	NPC219498
0.7091	Intermediate Similarity	NPC308412
0.7091	Intermediate Similarity	NPC134885
0.7091	Intermediate Similarity	NPC488247
0.7091	Intermediate Similarity	NPC210218
0.7091	Intermediate Similarity	NPC488248
0.7037	Intermediate Similarity	NPC47937
0.7018	Intermediate Similarity	NPC169511
0.7018	Intermediate Similarity	NPC287164
0.7018	Intermediate Similarity	NPC234077
0.6964	Remote Similarity	NPC488250
0.6842	Remote Similarity	NPC473478
0.6842	Remote Similarity	NPC69082
0.6842	Remote Similarity	NPC473651
0.6842	Remote Similarity	NPC488249
0.6842	Remote Similarity	NPC66346
0.6727	Remote Similarity	NPC477011
0.6724	Remote Similarity	NPC283085
0.6724	Remote Similarity	NPC130359
0.6724	Remote Similarity	NPC14901
0.6667	Remote Similarity	NPC91067
0.6667	Remote Similarity	NPC134807
0.6613	Remote Similarity	NPC488245
0.65	Remote Similarity	NPC239517
0.6481	Remote Similarity	NPC100921
0.6481	Remote Similarity	NPC475159
0.6481	Remote Similarity	NPC131002
0.6481	Remote Similarity	NPC473780
0.6481	Remote Similarity	NPC477018
0.6481	Remote Similarity	NPC604521
0.6452	Remote Similarity	NPC473663
0.6452	Remote Similarity	NPC473723
0.6452	Remote Similarity	NPC475173
0.6441	Remote Similarity	NPC231096
0.6441	Remote Similarity	NPC475581
0.6441	Remote Similarity	NPC62118
0.6441	Remote Similarity	NPC132496
0.6441	Remote Similarity	NPC107717
0.6441	Remote Similarity	NPC488252
0.6415	Remote Similarity	NPC112685
0.64	Remote Similarity	NPC608138
0.6271	Remote Similarity	NPC473707
0.625	Remote Similarity	NPC156804
0.6226	Remote Similarity	NPC73310
0.6226	Remote Similarity	NPC473529
0.6226	Remote Similarity	NPC180363
0.6226	Remote Similarity	NPC94875
0.6226	Remote Similarity	NPC11332
0.6226	Remote Similarity	NPC145914
0.6226	Remote Similarity	NPC601174
0.6226	Remote Similarity	NPC601403
0.6226	Remote Similarity	NPC603568
0.6226	Remote Similarity	NPC604330
0.6226	Remote Similarity	NPC608300
0.6226	Remote Similarity	NPC611200
0.6226	Remote Similarity	NPC611571
0.6167	Remote Similarity	NPC606740
0.6167	Remote Similarity	NPC608614
0.614	Remote Similarity	NPC473649
0.614	Remote Similarity	NPC473156
0.614	Remote Similarity	NPC154097
0.614	Remote Similarity	NPC163093
0.614	Remote Similarity	NPC159750
0.614	Remote Similarity	NPC73248
0.614	Remote Similarity	NPC282815
0.614	Remote Similarity	NPC470401
0.614	Remote Similarity	NPC600956
0.614	Remote Similarity	NPC610454
0.6129	Remote Similarity	NPC480081
0.6066	Remote Similarity	NPC233551
0.6066	Remote Similarity	NPC40376
0.6066	Remote Similarity	NPC21208
0.6034	Remote Similarity	NPC473671
0.6034	Remote Similarity	NPC475268
0.6034	Remote Similarity	NPC470400
0.6034	Remote Similarity	NPC77871
0.6034	Remote Similarity	NPC9678
0.6034	Remote Similarity	NPC319036
0.6034	Remote Similarity	NPC604764
0.6034	Remote Similarity	NPC605867
0.6	Remote Similarity	NPC20339
0.5932	Remote Similarity	NPC132940
0.5902	Remote Similarity	NPC258068
0.5902	Remote Similarity	NPC476583
0.5893	Remote Similarity	NPC25764
0.5893	Remote Similarity	NPC235809
0.5893	Remote Similarity	NPC329829
0.5893	Remote Similarity	NPC39279
0.5893	Remote Similarity	NPC39167
0.5893	Remote Similarity	NPC292809
0.5893	Remote Similarity	NPC202055
0.5893	Remote Similarity	NPC606804
0.5893	Remote Similarity	NPC607425
0.5893	Remote Similarity	NPC608574
0.5833	Remote Similarity	NPC309211
0.5833	Remote Similarity	NPC329838
0.5833	Remote Similarity	NPC20533
0.5833	Remote Similarity	NPC477010
0.5806	Remote Similarity	NPC477014
0.5806	Remote Similarity	NPC477013
0.5763	Remote Similarity	NPC241360
0.5763	Remote Similarity	NPC293136
0.5763	Remote Similarity	NPC480079
0.5758	Remote Similarity	NPC482766
0.5758	Remote Similarity	NPC279267
0.5645	Remote Similarity	NPC120398
0.5645	Remote Similarity	NPC473995
0.5645	Remote Similarity	NPC471567
0.5593	Remote Similarity	NPC144415
0.5593	Remote Similarity	NPC600524
0.5593	Remote Similarity	NPC607439
0.5593	Remote Similarity	NPC608157
0.5593	Remote Similarity	NPC608355
0.5556	Remote Similarity	NPC89001
0.55	Remote Similarity	NPC219652
0.55	Remote Similarity	NPC473840
0.541	Remote Similarity	NPC473904
0.541	Remote Similarity	NPC65930
0.5333	Remote Similarity	NPC488246
0.5333	Remote Similarity	NPC480080
0.5323	Remote Similarity	NPC485250
0.5323	Remote Similarity	NPC605396
0.5294	Remote Similarity	NPC477017
0.5294	Remote Similarity	NPC477016
0.5246	Remote Similarity	NPC25703
0.5238	Remote Similarity	NPC11456
0.5238	Remote Similarity	NPC477012
0.5152	Remote Similarity	NPC473520
0.5152	Remote Similarity	NPC280612
0.5079	Remote Similarity	NPC329615
0.5075	Remote Similarity	NPC477015

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488623 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6665
0.1-0.2	2457
0.2-0.3	28
0.3-0.4	0
0.4-0.5	0
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