NPASS Compound

Natural Product: NPC476583

Natural Product ID	NPC476583
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Squamostatin-A
IUPAC Name	(2R)-4-[9-[(2R,5S)-5-[(1R,4R)-4-[(2S,5S)-5-[(1S,5R)-1,5-dihydroxyundecyl]oxolan-2-yl]-1,4-dihydroxybutyl]oxolan-2-yl]nonyl]-2-methyl-2H-furan-5-one
Synonyms	Squamostatin-A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44591858
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 111113 0 0 0 0 0 0 0 0999 V2000 13.9933 0.7069 0.7025 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7865 0.1154 -0.6589 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3597 -0.2734 -0.9524 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4288 0.9258 -0.8644 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0445 0.4324 -1.1805 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9804 1.4799 -1.1453 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8493 2.1263 0.2132 C 0 0 2 0 0 0 0 0 0 0 0 0 8.5069 1.1551 1.2876 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1982 0.4128 1.0758 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0249 1.3054 1.0085 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7439 0.5426 0.7985 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4180 -0.4728 1.8522 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1463 -1.7790 1.6571 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0254 -2.7930 1.3597 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0131 -1.8127 0.7266 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0773 -0.8076 1.6791 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6271 -2.4257 0.7685 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6220 -1.3039 0.7696 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7786 -0.4838 -0.4599 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1285 0.6899 -0.5893 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5821 0.3758 -0.5945 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4138 1.6701 -0.5998 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8169 0.9843 -0.4731 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4524 -0.1810 0.3877 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0669 -0.1962 0.5700 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8414 -1.5243 -0.1124 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2840 -1.7766 -0.2322 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0242 -0.8724 -1.1540 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5013 -1.3113 -1.2420 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2011 -0.3911 -2.1945 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1852 1.0119 -1.7793 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7044 1.4756 -0.4839 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1298 1.2472 -0.1763 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5144 -0.1603 0.0052 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9771 -0.3168 0.3245 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9231 0.5648 0.4566 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.2123 -0.0822 0.7732 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.9066 -1.4419 0.8594 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.5713 -1.6188 0.5748 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9554 -2.7308 0.5358 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.2460 0.1953 -0.3097 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1562 1.2731 -1.8491 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4193 -3.3996 -0.1733 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7150 1.5440 0.9742 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9998 3.2076 0.2061 O 0 0 0 0 0 0 0 0 0 0 0 0 13.9232 1.8191 0.6246 H 0 0 0 0 0 0 0 0 0 0 0 0 15.0163 0.4098 1.0524 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2217 0.2928 1.3963 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3757 -0.8475 -0.7120 H 0 0 0 0 0 0 0 0 0 0 0 0 14.1945 0.7543 -1.4606 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9874 -1.0239 -0.2340 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3370 -0.6559 -1.9915 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7544 1.6875 -1.6137 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5326 1.3815 0.1389 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8009 -0.3270 -0.3992 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0933 -0.0666 -2.1691 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0187 0.9741 -1.3671 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1540 2.2879 -1.8957 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8962 2.4935 0.4555 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3623 1.7506 2.2376 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2772 0.4042 1.4898 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1275 -0.3428 1.9182 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3414 -0.1774 0.1536 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1404 1.9142 0.0539 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9652 2.0623 1.8064 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6428 0.1993 -0.2254 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5537 -0.0786 2.8585 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7915 -1.8267 0.7664 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6043 -2.1005 2.6037 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3424 -3.5655 0.6566 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5631 -3.1678 2.2899 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3203 -1.5475 -0.2758 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5558 -2.8800 1.8116 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4257 -1.7191 0.8339 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8293 -0.7126 1.7071 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8277 -0.1101 -0.5497 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6163 -1.1626 -1.3382 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0789 1.4927 0.1460 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8992 -0.2123 -1.4811 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3322 2.2327 -1.5211 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2812 2.1986 0.3395 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5087 1.7034 -0.0207 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0283 0.7278 -1.5404 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8947 -0.0361 1.4360 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3122 -2.3395 0.4728 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4063 -1.6531 -1.1675 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5144 -2.8649 -0.4526 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7159 -1.5987 0.8201 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6193 -0.9222 -2.1644 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0566 0.1460 -0.7089 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4449 -2.3565 -1.6193 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9027 -1.3250 -0.2280 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5578 -0.3829 -3.1842 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1222 -0.8418 -2.5566 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6416 1.6615 -2.6318 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0974 1.3764 -1.8540 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0599 0.9365 0.3180 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4106 2.5633 -0.2899 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7144 1.6753 -1.0674 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4228 1.8919 0.7031 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3077 -0.8266 -0.8092 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9117 -0.5636 0.8838 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7896 1.6296 0.3502 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.5525 0.3600 1.7513 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.1897 0.4519 0.1741 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.8808 0.9848 -0.9671 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.3887 -0.7791 -0.8552 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3553 0.5222 -2.4949 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0723 -3.4081 -0.9157 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9454 2.0841 1.7920 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4945 4.0660 0.0390 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 15 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 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 1 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 37 41 1 0 20 42 1 0 17 43 1 0 11 44 1 0 7 45 1 0 16 12 1 0 25 21 1 0 39 35 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 0 2 50 1 0 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 5 55 1 0 5 56 1 0 6 57 1 0 6 58 1 0 7 59 1 1 8 60 1 0 8 61 1 0 9 62 1 0 9 63 1 0 10 64 1 0 10 65 1 0 11 66 1 6 12 67 1 1 13 68 1 0 13 69 1 0 14 70 1 0 14 71 1 0 15 72 1 6 17 73 1 1 18 74 1 0 18 75 1 0 19 76 1 0 19 77 1 0 20 78 1 1 21 79 1 6 22 80 1 0 22 81 1 0 23 82 1 0 23 83 1 0 24 84 1 1 26 85 1 0 26 86 1 0 27 87 1 0 27 88 1 0 28 89 1 0 28 90 1 0 29 91 1 0 29 92 1 0 30 93 1 0 30 94 1 0 31 95 1 0 31 96 1 0 32 97 1 0 32 98 1 0 33 99 1 0 33100 1 0 34101 1 0 34102 1 0 36103 1 0 37104 1 1 41105 1 0 41106 1 0 41107 1 0 42108 1 0 43109 1 0 44110 1 0 45111 1 0 M END

Standard InCHIKey	HKIHGTSLUYNNHM-QYGGFNKRSA-N
Standard InCHI	InChI=1S/C37H66O8/c1-3-4-5-12-16-29(38)17-14-19-31(39)35-24-25-36(45-35)33(41)22-21-32(40)34-23-20-30(44-34)18-13-10-8-6-7-9-11-15-28-26-27(2)43-37(28)42/h26-27,29-36,38-41H,3-25H2,1-2H3/t27-,29-,30-,31+,32-,33-,34+,35+,36+/m1/s1
SMILES	CCCCCC[C@H](CCC[C@@H]([C@@H]1CC[C@H](O1)[C@@H](CC[C@H]([C@@H]2CC[C@H](O2)CCCCCCCCCC3=C[C@H](OC3=O)C)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.48	Volume:	687.887 ? Van der Waals volume.
Dense:	0.928	LogP:	3.988 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.222 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.203 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	25.0	Rigid Bonds:	16.0
TPSA:	125.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.063	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.02	Fsp³:	0.919
MCE-18:	45.07 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.843	Fluc inhibitor:	0.032 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.097 ? 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:	0.585	Promiscuous compounds:	0.393

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.193	MDCK Permeability:	-4.837
Pgp-inhibitor:	0.016	Pgp-substrate:	0.962
PAMPA:	0.356 ? 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):	0.003
20% Bioavailability (F20%):	0.989	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.602
Plasma Protein Binding (PPB):	93.318%	Volume Distribution (VD):	-0.084
Fu:	5.526% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.969
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.801
BSEP inhibitor:	0.989

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.02
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.605
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.985
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.945
HLM stability:	0.062 ? 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):

6.408

Half-life (T1/2):

1.1

ADMET: Toxicity

hERG Blockers:	0.356	hERG Blockers (10um):	0.712
Human Hepatotoxicity (H-HT):	0.757	Drug-induced Liver Injury (DILI):	0.176
AMES Toxicity:	0.171	Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.765	Skin Sensitization:	0.999
Carcinogencity:	0.138	Eye Corrosion:	0.108
Eye Irritation:	0.907	Respiratory Toxicity:	0.923
Drug-induced Neurotoxicity:	0.026	Ototoxicity:	0.894
Hematotoxicity:	0.121	Drug-induced Nephrotoxicity:	0.974
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.082
A549 Cytotoxicity:	0.931	Hek293 Cytotoxicity:	0.168
BCF:	1.429 ? 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:	5.178 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.314 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.693 ? 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
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	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	9
Inhibition	1
IC50	12

Activity Type	# Activity
Cell line	20
Others	2

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
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	8	ug/ml	PMID[12852747]
NPT306	Cell line	PC-3	Homo sapiens	ED50	>	20	ug/ml	PMID[12852747]
NPT307	Cell line	HOS	Homo sapiens	ED50	>	20	ug/ml	PMID[12852747]
NPT180	Cell line	HCT-8	Homo sapiens	ED50	>	20	ug/ml	PMID[12852747]
NPT308	Cell line	CAKI-1	Homo sapiens	ED50	>	20	ug/ml	PMID[12852747]
NPT81	Cell line	A549	Homo sapiens	ED50	>	20	ug/ml	PMID[12852747]
NPT309	Cell line	1A9	Homo sapiens	ED50	=	0.0087	ug/ml	PMID[12852747]
NPT310	Cell line	1A9/ptx-10	Homo sapiens	Inhibition	=	40	%	PMID[12852747]
NPT91	Cell line	KB	Homo sapiens	ED50	>	20	ug/ml	PMID[12852747]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	33	nM	PMID[19285863]
NPT515	Cell line	SGC-7901	Homo sapiens	IC50	=	97	nM	PMID[19285863]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	970	nM	PMID[19285863]
NPT81	Cell line	A549	Homo sapiens	IC50	=	0.21	ug/ml	PMID[22011319]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	0.45	ug/ml	PMID[22011319]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	0.15	ug/ml	PMID[22011319]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	0.83	ug/ml	PMID[22011319]
NPT659	Cell line	SMMC-7721	Homo sapiens	IC50	=	0.49	ug/ml	PMID[22011319]
NPT1097	Cell line	MKN-45	Homo sapiens	IC50	=	0.93	ug/ml	PMID[22011319]
NPT81	Cell line	A549	Homo sapiens	IC50	>	80000	nM	PMID[25582602]
NPT2	Others	Unspecified	n.a.	IC50	=	50	nM	PMID[19285863]
NPT2	Others	Unspecified	n.a.	IC50	=	2.6	nM	PMID[19285863]

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 NPC476583 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	17263
0.1-0.2	29658
0.2-0.3	2614
0.3-0.4	90
0.4-0.5	27
0.5-0.6	21
0.6-0.7	113
0.7-0.8	0
0.8-0.85	11
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC258068
0.9167	High Similarity	NPC241360
0.9167	High Similarity	NPC293136
0.8367	Intermediate Similarity	NPC156804
0.8333	Intermediate Similarity	NPC475159
0.8333	Intermediate Similarity	NPC131002
0.8333	Intermediate Similarity	NPC473780
0.8333	Intermediate Similarity	NPC604521
0.8235	Intermediate Similarity	NPC65930
0.8077	Intermediate Similarity	NPC329838
0.8077	Intermediate Similarity	NPC329615
0.8077	Intermediate Similarity	NPC20621
0.8077	Intermediate Similarity	NPC318963
0.8077	Intermediate Similarity	NPC605101
0.7963	Intermediate Similarity	NPC477014
0.7963	Intermediate Similarity	NPC477013
0.7736	Intermediate Similarity	NPC20533
0.7708	Intermediate Similarity	NPC73310
0.7708	Intermediate Similarity	NPC473529
0.7708	Intermediate Similarity	NPC180363
0.7708	Intermediate Similarity	NPC94875
0.7708	Intermediate Similarity	NPC11332
0.7708	Intermediate Similarity	NPC145914
0.7708	Intermediate Similarity	NPC601174
0.7708	Intermediate Similarity	NPC601403
0.7708	Intermediate Similarity	NPC603568
0.7708	Intermediate Similarity	NPC604330
0.7708	Intermediate Similarity	NPC608300
0.7708	Intermediate Similarity	NPC611200
0.7708	Intermediate Similarity	NPC611571
0.7692	Intermediate Similarity	NPC473671
0.7692	Intermediate Similarity	NPC475268
0.7692	Intermediate Similarity	NPC470400
0.7692	Intermediate Similarity	NPC77871
0.7692	Intermediate Similarity	NPC9678
0.7692	Intermediate Similarity	NPC319036
0.7692	Intermediate Similarity	NPC605867
0.7636	Intermediate Similarity	NPC320458
0.76	Intermediate Similarity	NPC100921
0.76	Intermediate Similarity	NPC477018
0.7547	Intermediate Similarity	NPC132940
0.75	Intermediate Similarity	NPC473156
0.75	Intermediate Similarity	NPC163093
0.75	Intermediate Similarity	NPC282815
0.75	Intermediate Similarity	NPC600956
0.7321	Intermediate Similarity	NPC480082
0.7273	Intermediate Similarity	NPC473478
0.7273	Intermediate Similarity	NPC473651
0.7273	Intermediate Similarity	NPC66346
0.7255	Intermediate Similarity	NPC329829
0.7241	Intermediate Similarity	NPC253801
0.717	Intermediate Similarity	NPC488632
0.717	Intermediate Similarity	NPC610454
0.7143	Intermediate Similarity	NPC231096
0.7143	Intermediate Similarity	NPC475581
0.7143	Intermediate Similarity	NPC283085
0.7143	Intermediate Similarity	NPC62118
0.7143	Intermediate Similarity	NPC107717
0.7143	Intermediate Similarity	NPC488252
0.7143	Intermediate Similarity	NPC473995
0.7115	Intermediate Similarity	NPC488253
0.7115	Intermediate Similarity	NPC488251
0.7069	Intermediate Similarity	NPC473520
0.7069	Intermediate Similarity	NPC322529
0.7037	Intermediate Similarity	NPC604764
0.6981	Remote Similarity	NPC232555
0.6981	Remote Similarity	NPC171174
0.6981	Remote Similarity	NPC114694
0.6981	Remote Similarity	NPC485248
0.6981	Remote Similarity	NPC142117
0.6981	Remote Similarity	NPC480249
0.6981	Remote Similarity	NPC485249
0.6981	Remote Similarity	NPC240695
0.6923	Remote Similarity	NPC107986
0.6923	Remote Similarity	NPC25764
0.6923	Remote Similarity	NPC235809
0.6923	Remote Similarity	NPC223871
0.6923	Remote Similarity	NPC231009
0.6923	Remote Similarity	NPC103284
0.6923	Remote Similarity	NPC110710
0.6923	Remote Similarity	NPC39279
0.6923	Remote Similarity	NPC1083
0.6923	Remote Similarity	NPC39167
0.6923	Remote Similarity	NPC82795
0.6923	Remote Similarity	NPC292809
0.6923	Remote Similarity	NPC286338
0.6923	Remote Similarity	NPC202055
0.6923	Remote Similarity	NPC603931
0.6923	Remote Similarity	NPC604237
0.6923	Remote Similarity	NPC606804
0.6923	Remote Similarity	NPC607425
0.6923	Remote Similarity	NPC608574
0.6852	Remote Similarity	NPC473649
0.6852	Remote Similarity	NPC154097
0.6852	Remote Similarity	NPC144415
0.6852	Remote Similarity	NPC159750
0.6852	Remote Similarity	NPC73248
0.6852	Remote Similarity	NPC470401
0.6852	Remote Similarity	NPC477011
0.6852	Remote Similarity	NPC607439
0.6852	Remote Similarity	NPC608157
0.6842	Remote Similarity	NPC169511
0.6842	Remote Similarity	NPC287164
0.6842	Remote Similarity	NPC234077
0.6842	Remote Similarity	NPC132496
0.6792	Remote Similarity	NPC473669
0.6786	Remote Similarity	NPC309211
0.6786	Remote Similarity	NPC477010
0.6731	Remote Similarity	NPC606043
0.6727	Remote Similarity	NPC219652
0.6727	Remote Similarity	NPC473840
0.6667	Remote Similarity	NPC182383
0.6667	Remote Similarity	NPC477015
0.6613	Remote Similarity	NPC477017
0.6613	Remote Similarity	NPC477016
0.6607	Remote Similarity	NPC178215
0.6552	Remote Similarity	NPC120398
0.6552	Remote Similarity	NPC471567
0.6552	Remote Similarity	NPC606740
0.6552	Remote Similarity	NPC608614
0.6545	Remote Similarity	NPC134865
0.6545	Remote Similarity	NPC103523
0.6545	Remote Similarity	NPC488627
0.6545	Remote Similarity	NPC47937
0.6545	Remote Similarity	NPC488631
0.65	Remote Similarity	NPC91067
0.65	Remote Similarity	NPC480081
0.65	Remote Similarity	NPC280612
0.6429	Remote Similarity	NPC280621
0.6429	Remote Similarity	NPC48338
0.6429	Remote Similarity	NPC488628
0.6379	Remote Similarity	NPC69082
0.6379	Remote Similarity	NPC488249
0.6316	Remote Similarity	NPC42598
0.625	Remote Similarity	NPC93794
0.625	Remote Similarity	NPC473504
0.625	Remote Similarity	NPC81778
0.625	Remote Similarity	NPC40066
0.623	Remote Similarity	NPC488630
0.623	Remote Similarity	NPC488625
0.623	Remote Similarity	NPC488626
0.6207	Remote Similarity	NPC485250
0.6207	Remote Similarity	NPC488250
0.6207	Remote Similarity	NPC605396
0.6167	Remote Similarity	NPC89001
0.6167	Remote Similarity	NPC233551
0.6167	Remote Similarity	NPC40376
0.6167	Remote Similarity	NPC21208
0.614	Remote Similarity	NPC25703
0.6102	Remote Similarity	NPC477012
0.6094	Remote Similarity	NPC482766
0.6094	Remote Similarity	NPC279267
0.6071	Remote Similarity	NPC81045
0.6071	Remote Similarity	NPC39754
0.6071	Remote Similarity	NPC171135
0.6071	Remote Similarity	NPC61257
0.6071	Remote Similarity	NPC320569
0.6071	Remote Similarity	NPC133730
0.6071	Remote Similarity	NPC191929
0.6071	Remote Similarity	NPC100454
0.6071	Remote Similarity	NPC242364
0.6071	Remote Similarity	NPC172821
0.6071	Remote Similarity	NPC274446
0.6071	Remote Similarity	NPC485251
0.6071	Remote Similarity	NPC151403
0.6071	Remote Similarity	NPC261952
0.6071	Remote Similarity	NPC605171
0.6034	Remote Similarity	NPC473687
0.6034	Remote Similarity	NPC204686
0.6034	Remote Similarity	NPC219498
0.6034	Remote Similarity	NPC308412
0.6034	Remote Similarity	NPC134885
0.6034	Remote Similarity	NPC488247
0.6034	Remote Similarity	NPC210218
0.6034	Remote Similarity	NPC488248
0.6032	Remote Similarity	NPC473663
0.6032	Remote Similarity	NPC473723
0.6032	Remote Similarity	NPC475173
0.5965	Remote Similarity	NPC600524
0.5965	Remote Similarity	NPC608355
0.5932	Remote Similarity	NPC602738
0.5902	Remote Similarity	NPC488623
0.5902	Remote Similarity	NPC488624
0.5902	Remote Similarity	NPC488629
0.5882	Remote Similarity	NPC609415
0.5873	Remote Similarity	NPC473905
0.5833	Remote Similarity	NPC139418
0.5738	Remote Similarity	NPC130359
0.5738	Remote Similarity	NPC14901
0.5667	Remote Similarity	NPC134807
0.5593	Remote Similarity	NPC475616
0.5577	Remote Similarity	NPC608138
0.5574	Remote Similarity	NPC20339
0.5517	Remote Similarity	NPC488234
0.55	Remote Similarity	NPC480251
0.55	Remote Similarity	NPC480250
0.5424	Remote Similarity	NPC482767
0.5424	Remote Similarity	NPC475260
0.5424	Remote Similarity	NPC488621

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476583 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6611
0.1-0.2	2488
0.2-0.3	51
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