NPASS Compound

Natural Product: NPC473663

Natural Product ID	NPC473663
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Arianacin Formal
IUPAC Name	(2S)-4-[(2R)-2-hydroxy-9-[(4S,7R)-7-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]-1,3-dioxepan-4-yl]nonyl]-2-methyl-2H-furan-5-one
Synonyms	Arianacin Formal
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL448493
PubChem CID	10675223
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 107109 0 0 0 0 0 0 0 0999 V2000 -15.7488 1.4393 2.0733 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.0843 0.5864 1.0176 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5873 0.7058 1.1963 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8387 -0.1238 0.1736 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3454 0.0767 0.4591 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5598 -0.7250 -0.5262 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0659 -0.6009 -0.3328 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5745 0.7969 -0.4710 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0526 0.8570 -0.2545 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3737 0.0112 -1.2618 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8573 0.0512 -1.0464 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2528 1.3824 -1.1673 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7790 1.5233 -1.0256 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2028 1.0861 0.3135 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2646 -0.3979 0.4204 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8370 -0.8040 0.7403 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2007 0.4937 1.1613 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8321 1.4126 0.3416 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2805 0.4101 0.8068 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9479 -0.5575 1.7432 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2879 -1.0424 1.2007 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1237 -1.5533 -0.1986 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5122 -0.5712 -1.0960 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5118 0.3901 -1.1534 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3554 0.0065 -0.5261 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9305 -2.8013 -0.4314 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4097 -2.6344 -0.2195 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0764 -1.6391 -1.0869 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5925 -1.5209 -0.8599 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2895 -2.7913 -1.1389 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7275 -2.8802 -0.9173 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7238 -2.0632 -1.6037 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6971 -0.5917 -1.3698 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8619 -0.2481 0.0982 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8357 1.2226 0.2826 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7513 2.0187 0.7875 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2742 3.4213 0.7656 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9985 3.3476 0.1869 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6876 2.0370 -0.1181 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6091 1.6115 -0.6471 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1032 3.9331 2.1936 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9164 -0.0837 -1.9662 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4716 2.9259 -1.1518 O 0 0 0 0 0 0 0 0 0 0 0 0 -16.7339 1.8031 1.7138 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.8421 0.9044 3.0575 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.1417 2.3391 2.2949 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.3448 1.0296 0.0361 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.4072 -0.4644 1.0556 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3047 0.3336 2.1950 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2829 1.7639 1.0486 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0503 -1.1951 0.2394 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0313 0.2726 -0.8565 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1902 -0.3700 1.4673 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1783 1.1549 0.4276 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7892 -1.8092 -0.3112 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8530 -0.5779 -1.5786 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6220 -1.2012 -1.1832 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7137 -1.0545 0.5952 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7608 1.1878 -1.5060 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0076 1.5166 0.2188 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7209 1.9278 -0.4019 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7918 0.6135 0.7912 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5556 0.3014 -2.2984 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6359 -1.0714 -1.1888 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7433 -0.3678 -0.0050 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4672 -0.7083 -1.7568 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5179 1.7998 -2.1811 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7858 2.0881 -0.4511 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2611 1.0029 -1.8428 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7243 1.6103 1.1400 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8682 -0.7513 1.3068 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5185 -0.9379 -0.5032 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3026 -1.1185 -0.2027 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7919 -1.5906 1.5219 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3463 0.7109 2.2330 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7226 1.4106 0.9683 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2085 0.0335 2.6688 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3003 -1.3807 2.0395 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7443 -1.7713 1.8774 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9579 -0.1616 1.1807 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0228 -1.7729 -0.3443 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8515 1.4091 -0.8729 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2546 0.4757 -2.2516 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5461 -3.6040 0.2420 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7883 -3.1071 -1.5080 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9072 -3.6419 -0.2075 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5090 -2.3033 0.8626 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8953 -1.7915 -2.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7088 -0.5986 -0.8345 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8749 -0.8051 -1.6967 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7867 -1.0500 0.1002 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0810 -3.0429 -2.2305 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8273 -3.6390 -0.5169 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9885 -4.0054 -1.0478 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9141 -2.8100 0.2290 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7523 -2.4511 -1.2679 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7755 -2.2907 -2.7175 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8721 -0.0971 -1.8556 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8711 -0.6165 0.3920 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0833 -0.7608 0.6876 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7140 1.6720 1.1625 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9521 4.0844 0.1921 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4068 4.7868 2.1513 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5657 3.1043 2.7336 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0587 4.1440 2.6836 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6846 0.0254 -2.9275 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9162 3.2963 -1.9535 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 17 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 22 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 33 42 1 0 13 43 1 0 18 14 1 0 25 19 1 0 39 35 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 0 2 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 5 53 1 0 5 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 8 59 1 0 8 60 1 0 9 61 1 0 9 62 1 0 10 63 1 0 10 64 1 0 11 65 1 0 11 66 1 0 12 67 1 0 12 68 1 0 13 69 1 0 14 70 1 0 15 71 1 0 15 72 1 0 16 73 1 0 16 74 1 0 17 75 1 0 19 76 1 0 20 77 1 0 20 78 1 0 21 79 1 0 21 80 1 0 22 81 1 0 24 82 1 0 24 83 1 0 26 84 1 0 26 85 1 0 27 86 1 0 27 87 1 0 28 88 1 0 28 89 1 0 29 90 1 0 29 91 1 0 30 92 1 0 30 93 1 0 31 94 1 0 31 95 1 0 32 96 1 0 32 97 1 0 33 98 1 0 34 99 1 0 34100 1 0 36101 1 0 37102 1 0 41103 1 0 41104 1 0 41105 1 0 42106 1 0 43107 1 0 M END

Standard InCHIKey	LAAZBSDOLUOJBG-NRLBRZFASA-N
Standard InCHI	InChI=1S/C36H64O7/c1-3-4-5-6-7-8-9-10-14-17-20-32(38)33-23-24-35(43-33)34-22-21-31(40-27-41-34)19-16-13-11-12-15-18-30(37)26-29-25-28(2)42-36(29)39/h25,28,30-35,37-38H,3-24,26-27H2,1-2H3/t28-,30+,31-,32+,33+,34+,35+/m0/s1
SMILES	CCCCCCCCCCCCC(C1CCC(O1)C2CCC(OCO2)CCCCCCCC(CC3=CC(OC3=O)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	608.47	Volume:	661.801 ? Van der Waals volume.
Dense:	0.919	LogP:	7.256 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.784 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.666 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	23.0	Rigid Bonds:	18.0
TPSA:	94.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.089	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.671	Fsp³:	0.917
MCE-18:	41.217 ? 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:	0.599	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.058 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.348	Promiscuous compounds:	0.003

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.129	MDCK Permeability:	-4.714
Pgp-inhibitor:	0.0	Pgp-substrate:	0.034
PAMPA:	0.01 ? 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):	0.9
20% Bioavailability (F20%):	0.728	30% Bioavailability (F30%):	0.981
50% Bioavailability (F50%):	0.894

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.996
Plasma Protein Binding (PPB):	96.546%	Volume Distribution (VD):	0.833
Fu:	2.892% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.064
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.079
BSEP inhibitor:	0.761

ADMET: Metabolism

CYP1A2-inhibitor:	0.008	CYP1A2-substrate:	0.025
CYP2C19-inhibitor:	0.995	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.86	CYP2D6-substrate:	0.963
CYP3A4-inhibitor:	0.178	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.902	CYP2C8-inhibitor:	0.262
HLM stability:	0.035 ? 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):

5.535

Half-life (T1/2):

1.102

ADMET: Toxicity

hERG Blockers:	0.794	hERG Blockers (10um):	0.904
Human Hepatotoxicity (H-HT):	0.551	Drug-induced Liver Injury (DILI):	0.092
AMES Toxicity:	0.042	Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.548	Skin Sensitization:	0.998
Carcinogencity:	0.059	Eye Corrosion:	0.0
Eye Irritation:	0.319	Respiratory Toxicity:	0.821
Drug-induced Neurotoxicity:	0.06	Ototoxicity:	0.902
Hematotoxicity:	0.03	Drug-induced Nephrotoxicity:	0.841
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.067
A549 Cytotoxicity:	0.747	Hek293 Cytotoxicity:	0.445
BCF:	0.925 ? 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:	4.873 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.31 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.532 ? 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
Inhibition	1
IC50	3

Activity Type	# Activity
Cell line	3
Organism	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
NPT81	Cell line	A549	Homo sapiens	IC50	=	0.02	ug.mL-1	PMID[17938185]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	8.5	ug.mL-1	PMID[19267453]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	1.0	ug.mL-1	PMID[18183025]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	28.0	%	PMID[15332869]

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 NPC473663 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	16670
0.1-0.2	31226
0.2-0.3	1675
0.3-0.4	61
0.4-0.5	27
0.5-0.6	52
0.6-0.7	103
0.7-0.8	0
0.8-0.85	4
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	NPC473723
1.0	High Similarity	NPC475173
0.8364	Intermediate Similarity	NPC169511
0.8364	Intermediate Similarity	NPC287164
0.8364	Intermediate Similarity	NPC234077
0.8	Intermediate Similarity	NPC602738
0.7931	Intermediate Similarity	NPC91067
0.7925	Intermediate Similarity	NPC81045
0.7925	Intermediate Similarity	NPC39754
0.7925	Intermediate Similarity	NPC171135
0.7925	Intermediate Similarity	NPC61257
0.7925	Intermediate Similarity	NPC320569
0.7925	Intermediate Similarity	NPC133730
0.7925	Intermediate Similarity	NPC191929
0.7925	Intermediate Similarity	NPC100454
0.7925	Intermediate Similarity	NPC242364
0.7925	Intermediate Similarity	NPC172821
0.7925	Intermediate Similarity	NPC274446
0.7925	Intermediate Similarity	NPC485251
0.7925	Intermediate Similarity	NPC151403
0.7925	Intermediate Similarity	NPC261952
0.7925	Intermediate Similarity	NPC605171
0.7778	Intermediate Similarity	NPC93794
0.7778	Intermediate Similarity	NPC473504
0.7778	Intermediate Similarity	NPC81778
0.7778	Intermediate Similarity	NPC40066
0.7627	Intermediate Similarity	NPC473520
0.7544	Intermediate Similarity	NPC473707
0.75	Intermediate Similarity	NPC42598
0.7368	Intermediate Similarity	NPC20621
0.7368	Intermediate Similarity	NPC318963
0.7368	Intermediate Similarity	NPC605101
0.7241	Intermediate Similarity	NPC473478
0.7241	Intermediate Similarity	NPC473651
0.7241	Intermediate Similarity	NPC66346
0.7119	Intermediate Similarity	NPC283085
0.7037	Intermediate Similarity	NPC606043
0.6964	Remote Similarity	NPC182383
0.6909	Remote Similarity	NPC107986
0.6909	Remote Similarity	NPC223871
0.6909	Remote Similarity	NPC231009
0.6909	Remote Similarity	NPC103284
0.6909	Remote Similarity	NPC110710
0.6909	Remote Similarity	NPC1083
0.6909	Remote Similarity	NPC82795
0.6909	Remote Similarity	NPC286338
0.6909	Remote Similarity	NPC603931
0.6909	Remote Similarity	NPC604237
0.6885	Remote Similarity	NPC239517
0.6833	Remote Similarity	NPC231096
0.6833	Remote Similarity	NPC475581
0.6833	Remote Similarity	NPC62118
0.6833	Remote Similarity	NPC132496
0.6833	Remote Similarity	NPC107717
0.6833	Remote Similarity	NPC488252
0.6786	Remote Similarity	NPC488253
0.6786	Remote Similarity	NPC473669
0.6786	Remote Similarity	NPC488251
0.6774	Remote Similarity	NPC488630
0.6774	Remote Similarity	NPC488625
0.6774	Remote Similarity	NPC488626
0.6667	Remote Similarity	NPC232555
0.6667	Remote Similarity	NPC171174
0.6667	Remote Similarity	NPC114694
0.6667	Remote Similarity	NPC485248
0.6667	Remote Similarity	NPC142117
0.6667	Remote Similarity	NPC480249
0.6667	Remote Similarity	NPC485249
0.6667	Remote Similarity	NPC240695
0.6552	Remote Similarity	NPC488632
0.6552	Remote Similarity	NPC473649
0.6552	Remote Similarity	NPC473156
0.6552	Remote Similarity	NPC134865
0.6552	Remote Similarity	NPC154097
0.6552	Remote Similarity	NPC103523
0.6552	Remote Similarity	NPC159750
0.6552	Remote Similarity	NPC73248
0.6552	Remote Similarity	NPC282815
0.6552	Remote Similarity	NPC488627
0.6552	Remote Similarity	NPC47937
0.6552	Remote Similarity	NPC488631
0.6552	Remote Similarity	NPC470401
0.6552	Remote Similarity	NPC600956
0.6552	Remote Similarity	NPC610454
0.6508	Remote Similarity	NPC480081
0.6452	Remote Similarity	NPC488623
0.6452	Remote Similarity	NPC488624
0.6452	Remote Similarity	NPC488629
0.6441	Remote Similarity	NPC280621
0.6441	Remote Similarity	NPC473671
0.6441	Remote Similarity	NPC475268
0.6441	Remote Similarity	NPC470400
0.6441	Remote Similarity	NPC77871
0.6441	Remote Similarity	NPC48338
0.6441	Remote Similarity	NPC9678
0.6441	Remote Similarity	NPC319036
0.6441	Remote Similarity	NPC488628
0.6441	Remote Similarity	NPC604764
0.6441	Remote Similarity	NPC605867
0.6364	Remote Similarity	NPC482766
0.6333	Remote Similarity	NPC178215
0.6333	Remote Similarity	NPC473687
0.6333	Remote Similarity	NPC204686
0.6333	Remote Similarity	NPC219498
0.6333	Remote Similarity	NPC308412
0.6333	Remote Similarity	NPC134885
0.6333	Remote Similarity	NPC488247
0.6333	Remote Similarity	NPC132940
0.6333	Remote Similarity	NPC210218
0.6333	Remote Similarity	NPC488248
0.6316	Remote Similarity	NPC25764
0.6316	Remote Similarity	NPC235809
0.6316	Remote Similarity	NPC39279
0.6316	Remote Similarity	NPC39167
0.6316	Remote Similarity	NPC292809
0.6316	Remote Similarity	NPC202055
0.6316	Remote Similarity	NPC606804
0.6316	Remote Similarity	NPC607425
0.6316	Remote Similarity	NPC608574
0.629	Remote Similarity	NPC130359
0.629	Remote Similarity	NPC473995
0.629	Remote Similarity	NPC14901
0.629	Remote Similarity	NPC606740
0.629	Remote Similarity	NPC608614
0.623	Remote Similarity	NPC20533
0.623	Remote Similarity	NPC488250
0.619	Remote Similarity	NPC233551
0.619	Remote Similarity	NPC40376
0.619	Remote Similarity	NPC21208
0.6129	Remote Similarity	NPC69082
0.6129	Remote Similarity	NPC488249
0.6119	Remote Similarity	NPC279267
0.6032	Remote Similarity	NPC120398
0.6032	Remote Similarity	NPC258068
0.6032	Remote Similarity	NPC471567
0.6032	Remote Similarity	NPC476583
0.6	Remote Similarity	NPC473791
0.6	Remote Similarity	NPC477011
0.6	Remote Similarity	NPC600524
0.6	Remote Similarity	NPC608355
0.5968	Remote Similarity	NPC134807
0.5965	Remote Similarity	NPC112685
0.5938	Remote Similarity	NPC89001
0.5926	Remote Similarity	NPC608138
0.5902	Remote Similarity	NPC219652
0.5902	Remote Similarity	NPC473840
0.5902	Remote Similarity	NPC241360
0.5902	Remote Similarity	NPC293136
0.5902	Remote Similarity	NPC480079
0.5806	Remote Similarity	NPC65930
0.5763	Remote Similarity	NPC100921
0.5763	Remote Similarity	NPC475159
0.5763	Remote Similarity	NPC131002
0.5763	Remote Similarity	NPC473780
0.5763	Remote Similarity	NPC477018
0.5763	Remote Similarity	NPC604521
0.5714	Remote Similarity	NPC485250
0.5714	Remote Similarity	NPC605396
0.5692	Remote Similarity	NPC477014
0.5692	Remote Similarity	NPC477013
0.5645	Remote Similarity	NPC25703
0.5625	Remote Similarity	NPC20339
0.5574	Remote Similarity	NPC156804
0.5517	Remote Similarity	NPC73310
0.5517	Remote Similarity	NPC473529
0.5517	Remote Similarity	NPC180363
0.5517	Remote Similarity	NPC94875
0.5517	Remote Similarity	NPC11332
0.5517	Remote Similarity	NPC145914
0.5517	Remote Similarity	NPC601174
0.5517	Remote Similarity	NPC601403
0.5517	Remote Similarity	NPC603568
0.5517	Remote Similarity	NPC604330
0.5517	Remote Similarity	NPC608300
0.5517	Remote Similarity	NPC611200
0.5517	Remote Similarity	NPC611571
0.5484	Remote Similarity	NPC163093
0.5469	Remote Similarity	NPC329615
0.5385	Remote Similarity	NPC480076
0.5385	Remote Similarity	NPC480077
0.5246	Remote Similarity	NPC329829
0.5238	Remote Similarity	NPC480078
0.5238	Remote Similarity	NPC480071
0.5231	Remote Similarity	NPC309211
0.5231	Remote Similarity	NPC329838
0.5231	Remote Similarity	NPC480075
0.5231	Remote Similarity	NPC477010
0.5224	Remote Similarity	NPC480082
0.5217	Remote Similarity	NPC473905
0.5217	Remote Similarity	NPC253801
0.5211	Remote Similarity	NPC477017
0.5211	Remote Similarity	NPC477016

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473663 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6644
0.1-0.2	2472
0.2-0.3	34
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