NPASS Compound

Natural Product: NPC329829

Natural Product ID	NPC329829
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Squafosacin B
IUPAC Name	(2S)-4-[(13R)-13-hydroxy-13-[(2R,5R)-5-[(1R)-1,8,9-trihydroxypentadecyl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL442949
PubChem CID	44577070
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 112113 0 0 0 0 0 0 0 0999 V2000 -15.7803 0.7273 0.3193 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.6308 -0.2750 0.4894 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.3871 0.5447 0.6692 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1750 -0.3220 0.8557 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9411 -1.2355 -0.3343 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7463 -2.0903 -0.1889 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4228 -1.3004 -0.0545 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1664 -0.4786 -1.2619 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8221 0.0601 -1.5328 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1639 0.9935 -0.6262 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7459 0.6272 0.7358 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7021 -0.4499 0.8389 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4198 -0.0593 0.1232 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7838 1.1818 0.6504 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5464 1.4922 -0.1474 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5129 0.4236 -0.1015 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8924 0.3588 1.2817 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5948 0.1288 0.8273 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6165 1.1583 -0.2567 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4947 0.7223 -1.0096 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7947 1.3246 -1.0958 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6203 0.1978 -1.5439 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3336 -0.5963 -0.4962 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1095 -1.7340 -1.1461 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1238 -1.2872 -2.1373 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1873 -0.3818 -1.6187 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0282 -0.9712 -0.5129 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7143 -2.2035 -1.0026 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5923 -2.8725 0.0166 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6884 -1.9343 0.4761 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5616 -1.4923 -0.6509 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6451 -0.5375 -0.2449 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5581 -1.1497 0.7642 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6443 -0.1785 1.1596 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8424 0.2540 2.3745 C 0 0 0 0 0 0 0 0 0 0 0 0 14.9890 1.1837 2.3602 C 0 0 0 0 0 0 0 0 0 0 0 0 15.4015 1.2227 1.0178 O 0 0 0 0 0 0 0 0 0 0 0 0 14.6029 0.3992 0.2469 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7026 0.2007 -1.0053 O 0 0 0 0 0 0 0 0 0 0 0 0 14.4364 2.5462 2.7850 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4741 2.2294 -2.1278 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9470 2.7061 0.2205 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0753 0.5971 -1.3980 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4330 -2.3172 -0.0173 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.6368 1.5953 0.9950 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.8357 1.0710 -0.7192 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.6896 0.2118 0.6627 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.5866 -0.8979 -0.4348 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.7689 -0.9021 1.3883 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2481 1.3136 -0.1168 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5002 1.1213 1.6338 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2953 0.3305 0.9832 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3207 -0.9272 1.7843 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8552 -1.9240 -0.3193 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9246 -0.6613 -1.2680 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8138 -2.6968 0.7483 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6854 -2.7703 -1.0534 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5298 -0.7787 0.8982 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4894 -1.1567 -2.1421 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1374 -0.8008 -1.8240 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9048 0.6018 -2.5430 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8500 1.9206 -0.5725 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2753 1.4366 -1.1829 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3873 1.5651 1.2808 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6028 0.3059 1.3470 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0452 -1.3730 0.3869 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5091 -0.6222 1.9099 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5599 -0.0785 -0.9556 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7083 -0.9066 0.3646 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4873 1.0968 1.7166 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4493 2.0716 0.6013 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9016 1.6009 -1.2157 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9125 -0.5688 -0.3839 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9105 1.3355 1.7544 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1828 -0.5001 1.8753 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5107 -0.8849 0.3731 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2802 0.2497 1.6462 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3518 2.1456 0.2079 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5400 1.9750 -0.4581 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1043 -0.4745 -2.2818 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4572 0.6546 -2.1780 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0433 0.0639 0.0760 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6887 -1.0514 0.2437 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3513 -2.3417 -1.6957 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5075 -2.3828 -0.3514 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6179 -0.7632 -2.9785 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5544 -2.2050 -2.6090 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7357 0.5433 -1.2297 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8415 -0.1108 -2.4670 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4120 -1.2605 0.3672 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7725 -0.2448 -0.1588 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2992 -2.0246 -1.9214 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9090 -2.9440 -1.2917 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0156 -3.1743 0.9017 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9955 -3.7903 -0.4493 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2937 -2.4337 1.2642 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2136 -1.0689 0.9648 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9799 -2.3968 -1.1712 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9565 -0.9493 -1.4354 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1764 -0.1617 -1.1434 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1286 0.3758 0.1698 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9581 -1.4136 1.6675 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0636 -2.0530 0.4250 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2527 -0.0261 3.2701 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8033 0.8680 3.0442 H 0 0 0 0 0 0 0 0 0 0 0 0 15.2468 3.2520 3.0379 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7159 2.3808 3.6061 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8388 2.9286 1.9167 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1693 1.7779 -2.9303 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6192 3.2312 0.6930 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8347 1.3496 -0.7967 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7998 -3.1498 0.3719 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 19 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 1 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 36 40 1 0 21 41 1 0 15 42 1 0 8 43 1 0 7 44 1 0 20 16 1 0 38 34 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 8 59 1 0 9 60 1 0 9 61 1 0 10 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 16 73 1 0 17 74 1 0 17 75 1 0 18 76 1 0 18 77 1 0 19 78 1 0 21 79 1 0 22 80 1 0 22 81 1 0 23 82 1 0 23 83 1 0 24 84 1 0 24 85 1 0 25 86 1 0 25 87 1 0 26 88 1 0 26 89 1 0 27 90 1 0 27 91 1 0 28 92 1 0 28 93 1 0 29 94 1 0 29 95 1 0 30 96 1 0 30 97 1 0 31 98 1 0 31 99 1 0 32100 1 0 32101 1 0 33102 1 0 33103 1 0 35104 1 0 36105 1 0 40106 1 0 40107 1 0 40108 1 0 41109 1 0 42110 1 0 43111 1 0 44112 1 0 M END

Standard InCHIKey	NNWVJTKJMJKOEU-CTBBGLRNSA-N
Standard InCHI	InChI=1S/C37H68O7/c1-3-4-5-17-22-31(38)32(39)23-18-14-15-20-25-34(41)36-27-26-35(44-36)33(40)24-19-13-11-9-7-6-8-10-12-16-21-30-28-29(2)43-37(30)42/h28-29,31-36,38-41H,3-27H2,1-2H3/t29-,31?,32?,33+,34+,35+,36+/m0/s1
SMILES	CCCCCCC(C(CCCCCCC(C1CCC(O1)C(CCCCCCCCCCCCC2=CC(OC2=O)C)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.5	Volume:	687.654 ? Van der Waals volume.
Dense:	0.908	LogP:	7.242 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.368 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.575 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	28.0	Rigid Bonds:	11.0
TPSA:	116.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	2.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.052	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.626	Fsp³:	0.919
MCE-18:	32.113 ? 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:	0.655	Fluc inhibitor:	0.011 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.026 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.398	Promiscuous compounds:	0.005

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.208	MDCK Permeability:	-4.833
Pgp-inhibitor:	0.001	Pgp-substrate:	0.242
PAMPA:	0.168 ? 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):	1.0
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.994
Plasma Protein Binding (PPB):	95.015%	Volume Distribution (VD):	0.684
Fu:	3.482% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.009
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.483
BSEP inhibitor:	0.658

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.575	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.997	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.007	CYP2D6-substrate:	0.508
CYP3A4-inhibitor:	0.212	CYP3A4-substrate:	0.009
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.547
HLM stability:	0.004 ? 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):

5.827

Half-life (T1/2):

1.393

ADMET: Toxicity

hERG Blockers:	0.681	hERG Blockers (10um):	0.949
Human Hepatotoxicity (H-HT):	0.511	Drug-induced Liver Injury (DILI):	0.119
AMES Toxicity:	0.073	Rat Oral Acute Toxicity:	0.16
Maximum Recommended Daily Dose:	0.7	Skin Sensitization:	0.989
Carcinogencity:	0.082	Eye Corrosion:	0.0
Eye Irritation:	0.031	Respiratory Toxicity:	0.413
Drug-induced Neurotoxicity:	0.056	Ototoxicity:	0.956
Hematotoxicity:	0.011	Drug-induced Nephrotoxicity:	0.64
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.064
A549 Cytotoxicity:	0.606	Hek293 Cytotoxicity:	0.572
BCF:	1.051 ? 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:	5.166 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.548 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.954 ? 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
IC50	5

Activity Type	# Activity
Cell line	4
Non-molecular	1

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
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	17040.0	nM	PMID[15664821]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	960.0	nM	PMID[15664821]
NPT81	Cell line	A549	Homo sapiens	IC50	=	660.0	nM	PMID[20627740]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	710.0	nM	PMID[15664821]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	720.0	nM	PMID[18419154]

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 NPC329829 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	15624
0.1-0.2	30101
0.2-0.3	3765
0.3-0.4	136
0.4-0.5	28
0.5-0.6	28
0.6-0.7	87
0.7-0.8	0
0.8-0.85	19
0.85-0.9	7
0.9-0.95	13
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.925	High Similarity	NPC73310
0.925	High Similarity	NPC473529
0.925	High Similarity	NPC180363
0.925	High Similarity	NPC94875
0.925	High Similarity	NPC11332
0.925	High Similarity	NPC145914
0.925	High Similarity	NPC601174
0.925	High Similarity	NPC601403
0.925	High Similarity	NPC603568
0.925	High Similarity	NPC604330
0.925	High Similarity	NPC608300
0.925	High Similarity	NPC611200
0.925	High Similarity	NPC611571
0.8696	High Similarity	NPC329838
0.8667	High Similarity	NPC219652
0.8667	High Similarity	NPC473840
0.8605	High Similarity	NPC475159
0.8605	High Similarity	NPC131002
0.8605	High Similarity	NPC473780
0.8605	High Similarity	NPC604521
0.8478	Intermediate Similarity	NPC65930
0.8261	Intermediate Similarity	NPC25703
0.825	Intermediate Similarity	NPC609415
0.8222	Intermediate Similarity	NPC156804
0.8182	Intermediate Similarity	NPC25764
0.8182	Intermediate Similarity	NPC235809
0.8182	Intermediate Similarity	NPC39279
0.8182	Intermediate Similarity	NPC39167
0.8182	Intermediate Similarity	NPC292809
0.8182	Intermediate Similarity	NPC202055
0.8182	Intermediate Similarity	NPC606804
0.8182	Intermediate Similarity	NPC607425
0.8182	Intermediate Similarity	NPC608574
0.8043	Intermediate Similarity	NPC163093
0.8043	Intermediate Similarity	NPC144415
0.8043	Intermediate Similarity	NPC600524
0.8043	Intermediate Similarity	NPC607439
0.8043	Intermediate Similarity	NPC608157
0.8043	Intermediate Similarity	NPC608355
0.7917	Intermediate Similarity	NPC329615
0.7917	Intermediate Similarity	NPC485250
0.7872	Intermediate Similarity	NPC241360
0.7872	Intermediate Similarity	NPC293136
0.7778	Intermediate Similarity	NPC100921
0.7778	Intermediate Similarity	NPC477018
0.7755	Intermediate Similarity	NPC477012
0.766	Intermediate Similarity	NPC473156
0.766	Intermediate Similarity	NPC134865
0.766	Intermediate Similarity	NPC103523
0.766	Intermediate Similarity	NPC282815
0.766	Intermediate Similarity	NPC488627
0.766	Intermediate Similarity	NPC488631
0.766	Intermediate Similarity	NPC477011
0.766	Intermediate Similarity	NPC600956
0.75	Intermediate Similarity	NPC473671
0.75	Intermediate Similarity	NPC475268
0.75	Intermediate Similarity	NPC470400
0.75	Intermediate Similarity	NPC77871
0.75	Intermediate Similarity	NPC9678
0.75	Intermediate Similarity	NPC319036
0.75	Intermediate Similarity	NPC605867
0.7451	Intermediate Similarity	NPC480082
0.7358	Intermediate Similarity	NPC473905
0.7358	Intermediate Similarity	NPC253801
0.7347	Intermediate Similarity	NPC132940
0.7292	Intermediate Similarity	NPC610454
0.7255	Intermediate Similarity	NPC258068
0.7255	Intermediate Similarity	NPC476583
0.72	Intermediate Similarity	NPC20533
0.72	Intermediate Similarity	NPC605396
0.7174	Intermediate Similarity	NPC606043
0.7115	Intermediate Similarity	NPC320458
0.7115	Intermediate Similarity	NPC477014
0.7115	Intermediate Similarity	NPC477013
0.7021	Intermediate Similarity	NPC107986
0.7021	Intermediate Similarity	NPC223871
0.7021	Intermediate Similarity	NPC231009
0.7021	Intermediate Similarity	NPC103284
0.7021	Intermediate Similarity	NPC110710
0.7021	Intermediate Similarity	NPC1083
0.7021	Intermediate Similarity	NPC82795
0.7021	Intermediate Similarity	NPC286338
0.7021	Intermediate Similarity	NPC603931
0.7021	Intermediate Similarity	NPC604237
0.6939	Remote Similarity	NPC473649
0.6939	Remote Similarity	NPC154097
0.6939	Remote Similarity	NPC159750
0.6939	Remote Similarity	NPC73248
0.6939	Remote Similarity	NPC470401
0.6923	Remote Similarity	NPC120398
0.6923	Remote Similarity	NPC473995
0.6923	Remote Similarity	NPC471567
0.6875	Remote Similarity	NPC488253
0.6875	Remote Similarity	NPC473669
0.6875	Remote Similarity	NPC488251
0.6863	Remote Similarity	NPC309211
0.6863	Remote Similarity	NPC477010
0.68	Remote Similarity	NPC604764
0.6735	Remote Similarity	NPC232555
0.6735	Remote Similarity	NPC171174
0.6735	Remote Similarity	NPC114694
0.6735	Remote Similarity	NPC485248
0.6735	Remote Similarity	NPC142117
0.6735	Remote Similarity	NPC480249
0.6735	Remote Similarity	NPC485249
0.6735	Remote Similarity	NPC240695
0.6731	Remote Similarity	NPC473478
0.6731	Remote Similarity	NPC473651
0.6731	Remote Similarity	NPC66346
0.6727	Remote Similarity	NPC477015
0.6604	Remote Similarity	NPC283085
0.6604	Remote Similarity	NPC132496
0.66	Remote Similarity	NPC488632
0.6545	Remote Similarity	NPC473520
0.6545	Remote Similarity	NPC322529
0.6545	Remote Similarity	NPC280612
0.6471	Remote Similarity	NPC280621
0.6471	Remote Similarity	NPC48338
0.6471	Remote Similarity	NPC488628
0.64	Remote Similarity	NPC81045
0.64	Remote Similarity	NPC39754
0.64	Remote Similarity	NPC171135
0.64	Remote Similarity	NPC182383
0.64	Remote Similarity	NPC61257
0.64	Remote Similarity	NPC320569
0.64	Remote Similarity	NPC133730
0.64	Remote Similarity	NPC191929
0.64	Remote Similarity	NPC100454
0.64	Remote Similarity	NPC242364
0.64	Remote Similarity	NPC172821
0.64	Remote Similarity	NPC274446
0.64	Remote Similarity	NPC485251
0.64	Remote Similarity	NPC151403
0.64	Remote Similarity	NPC261952
0.64	Remote Similarity	NPC605171
0.6346	Remote Similarity	NPC178215
0.6346	Remote Similarity	NPC473687
0.6346	Remote Similarity	NPC204686
0.6346	Remote Similarity	NPC219498
0.6346	Remote Similarity	NPC308412
0.6346	Remote Similarity	NPC134885
0.6346	Remote Similarity	NPC488247
0.6346	Remote Similarity	NPC210218
0.6346	Remote Similarity	NPC488248
0.6296	Remote Similarity	NPC231096
0.6296	Remote Similarity	NPC475581
0.6296	Remote Similarity	NPC62118
0.6296	Remote Similarity	NPC107717
0.6296	Remote Similarity	NPC488252
0.6296	Remote Similarity	NPC606740
0.6296	Remote Similarity	NPC608614
0.6275	Remote Similarity	NPC93794
0.6275	Remote Similarity	NPC473504
0.6275	Remote Similarity	NPC81778
0.6275	Remote Similarity	NPC40066
0.625	Remote Similarity	NPC91067
0.6226	Remote Similarity	NPC20621
0.6226	Remote Similarity	NPC318963
0.6226	Remote Similarity	NPC134807
0.6226	Remote Similarity	NPC488250
0.6226	Remote Similarity	NPC600188
0.6226	Remote Similarity	NPC605101
0.6182	Remote Similarity	NPC89001
0.6182	Remote Similarity	NPC233551
0.6182	Remote Similarity	NPC40376
0.6182	Remote Similarity	NPC21208
0.6111	Remote Similarity	NPC69082
0.6111	Remote Similarity	NPC488249
0.6038	Remote Similarity	NPC42598
0.6	Remote Similarity	NPC130359
0.6	Remote Similarity	NPC14901
0.5965	Remote Similarity	NPC480081
0.5962	Remote Similarity	NPC47937
0.5926	Remote Similarity	NPC602738
0.5893	Remote Similarity	NPC488623
0.5893	Remote Similarity	NPC488624
0.5893	Remote Similarity	NPC488629
0.5833	Remote Similarity	NPC477017
0.5833	Remote Similarity	NPC477016
0.575	Remote Similarity	NPC84038
0.5741	Remote Similarity	NPC478998
0.5741	Remote Similarity	NPC473904
0.5714	Remote Similarity	NPC169511
0.5714	Remote Similarity	NPC287164
0.5714	Remote Similarity	NPC234077
0.569	Remote Similarity	NPC488630
0.569	Remote Similarity	NPC488625
0.569	Remote Similarity	NPC488626
0.56	Remote Similarity	NPC112685
0.5574	Remote Similarity	NPC279267
0.5556	Remote Similarity	NPC480079
0.5532	Remote Similarity	NPC608138
0.5517	Remote Similarity	NPC239517
0.537	Remote Similarity	NPC488246
0.537	Remote Similarity	NPC480080
0.5263	Remote Similarity	NPC20339
0.5246	Remote Similarity	NPC473663
0.5246	Remote Similarity	NPC473723
0.5246	Remote Similarity	NPC475173

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC329829 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6214
0.1-0.2	2852
0.2-0.3	82
0.3-0.4	2
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