NPASS Compound

Natural Product: NPC473651

Natural Product ID	NPC473651
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Muricin A
IUPAC Name	(2S)-4-[(2R)-2-hydroxy-12-[(2S,5R)-5-[(1R)-1,8,9-trihydroxytetradecyl]oxolan-2-yl]dodecyl]-2-methyl-2H-furan-5-one
Synonyms	Muricin A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL448181
PubChem CID	44566988
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 106107 0 0 0 0 0 0 0 0999 V2000 12.7666 -0.0153 -1.5642 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7583 -1.0591 -0.4870 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4581 -1.2821 0.1656 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8228 -0.1871 0.9400 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4762 1.0624 0.2409 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8275 2.0728 1.0851 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5244 1.9594 1.7152 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7483 0.7381 1.8938 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3006 -0.0216 0.7077 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3977 0.7443 -0.2253 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1326 1.2070 0.4279 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2864 0.0790 0.9609 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8633 -0.8774 -0.1320 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0559 -0.1925 -1.2016 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7997 0.4271 -0.6655 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0083 1.1348 -1.7439 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4279 0.7958 -1.3828 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2275 -0.5538 -0.7193 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9861 -0.5075 -0.0808 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3295 -0.8098 0.3159 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6882 -0.7923 -0.3377 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7331 -1.0569 0.7211 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1333 -1.0385 0.1158 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0852 -1.3107 1.2312 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5626 -1.3097 0.7956 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8250 -2.3057 -0.2466 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1719 -2.4676 -0.8499 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3127 -2.7614 0.0328 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9186 -1.7321 0.9096 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7277 -0.6721 0.2961 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.3406 0.3142 -0.6674 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3138 1.3178 -0.4001 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2209 1.5048 -1.1195 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4570 2.6239 -0.5252 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1165 2.9545 0.6540 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2898 2.2458 0.7666 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2122 2.2787 1.6101 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0090 2.2666 -0.3941 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5314 -0.0471 1.3577 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6980 -1.1495 -2.1490 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5226 2.7808 2.8870 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9902 3.4140 0.6058 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7580 0.1549 -1.9847 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3494 -0.4010 -2.4789 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3104 0.9138 -1.3054 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5803 -0.8051 0.2394 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1561 -2.0122 -0.9635 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6118 -2.1345 0.9049 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7623 -1.7385 -0.5875 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9556 -0.6187 1.4600 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5525 0.0483 1.8009 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9093 0.8803 -0.7099 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4396 1.5525 -0.1303 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5830 2.1710 2.0417 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8543 2.6866 1.0345 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7976 1.0666 2.5009 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2110 0.0604 2.6272 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6901 -0.8939 1.0827 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0970 -0.4358 0.1180 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1131 0.0395 -1.0355 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8724 1.6058 -0.7041 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2879 1.9383 1.2422 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5320 1.7343 -0.3417 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3947 0.5293 1.4406 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7906 -0.5206 1.7347 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7174 -1.3728 -0.5875 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2045 -1.6378 0.3339 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6698 0.5590 -1.7636 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0059 1.2031 0.1107 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2445 0.6894 -2.7125 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2026 2.2207 -1.7593 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0415 0.7366 -2.2850 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7721 1.4984 -0.6154 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3127 -1.3683 -1.4657 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2692 -0.1074 1.1680 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1956 -1.8226 0.7457 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9212 0.1917 -0.7861 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7948 -1.5608 -1.1157 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7032 -0.3555 1.5648 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5636 -2.1028 1.0760 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2984 -0.0447 -0.3296 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1356 -1.8373 -0.6607 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0097 -0.5429 2.0224 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8616 -2.2810 1.7553 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0459 -1.7288 1.7564 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8548 -0.2835 0.6325 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5295 -3.3612 0.1016 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0598 -2.1424 -1.0786 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0748 -3.3956 -1.5300 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3885 -1.6643 -1.6077 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0136 -3.6803 0.6502 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1201 -3.2342 -0.6289 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6493 -2.3412 1.5817 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1491 -1.3411 1.6139 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6114 -1.2630 -0.2088 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1235 -0.1685 -1.6602 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2855 0.9365 -0.8999 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8762 0.9771 -1.9972 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5504 3.5477 -1.2040 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7353 1.7813 0.5608 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6774 1.6123 -1.2364 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3969 3.2030 -0.5351 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1890 0.4817 0.8445 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7839 -2.0753 -1.7941 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5774 2.9645 3.1133 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4061 3.5172 -0.2010 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 18 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 1 0 32 33 2 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 34 38 1 0 30 39 1 0 14 40 1 0 7 41 1 0 6 42 1 0 19 15 1 0 36 32 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 2 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 0 5 53 1 0 6 54 1 0 7 55 1 0 8 56 1 0 8 57 1 0 9 58 1 0 9 59 1 0 10 60 1 0 10 61 1 0 11 62 1 0 11 63 1 0 12 64 1 0 12 65 1 0 13 66 1 0 13 67 1 0 14 68 1 6 15 69 1 1 16 70 1 0 16 71 1 0 17 72 1 0 17 73 1 0 18 74 1 6 20 75 1 0 20 76 1 0 21 77 1 0 21 78 1 0 22 79 1 0 22 80 1 0 23 81 1 0 23 82 1 0 24 83 1 0 24 84 1 0 25 85 1 0 25 86 1 0 26 87 1 0 26 88 1 0 27 89 1 0 27 90 1 0 28 91 1 0 28 92 1 0 29 93 1 0 29 94 1 0 30 95 1 6 31 96 1 0 31 97 1 0 33 98 1 0 34 99 1 6 38100 1 0 38101 1 0 38102 1 0 39103 1 0 40104 1 0 41105 1 0 42106 1 0 M END

Standard InCHIKey	HHCQNIINSIODRY-PSSGGVRLSA-N
Standard InCHI	InChI=1S/C35H64O7/c1-3-4-13-20-31(37)32(38)21-16-11-12-17-22-33(39)34-24-23-30(42-34)19-15-10-8-6-5-7-9-14-18-29(36)26-28-25-27(2)41-35(28)40/h25,27,29-34,36-39H,3-24,26H2,1-2H3/t27-,29+,30-,31?,32?,33+,34+/m0/s1
SMILES	CCCCCC(C(CCCCCC[C@H]([C@H]1CC[C@@H](O1)CCCCCCCCCC[C@H](CC1=C[C@@H](OC1=O)C)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	596.47	Volume:	653.062 ? Van der Waals volume.
Dense:	0.913	LogP:	5.225 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.648 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.014 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	26.0	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:	0.062	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.596	Fsp³:	0.914
MCE-18:	32.239 ? 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:	0.78	Fluc inhibitor:	0.023 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.099 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.462	Promiscuous compounds:	0.114

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.162	MDCK Permeability:	-4.848
Pgp-inhibitor:	0.001	Pgp-substrate:	0.931
PAMPA:	0.346 ? 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):	0.062
20% Bioavailability (F20%):	0.968	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.951
Plasma Protein Binding (PPB):	93.906%	Volume Distribution (VD):	0.407
Fu:	5.075% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.193
OATP1B3 inhibitor:	0.875	BCRP inhibitor:	0.477
BSEP inhibitor:	0.88

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.008
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.745
CYP3A4-inhibitor:	0.013	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.953
HLM stability:	0.101 ? 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):

6.469

Half-life (T1/2):

1.015

ADMET: Toxicity

hERG Blockers:	0.321	hERG Blockers (10um):	0.781
Human Hepatotoxicity (H-HT):	0.587	Drug-induced Liver Injury (DILI):	0.268
AMES Toxicity:	0.432	Rat Oral Acute Toxicity:	0.144
Maximum Recommended Daily Dose:	0.93	Skin Sensitization:	0.997
Carcinogencity:	0.497	Eye Corrosion:	0.001
Eye Irritation:	0.448	Respiratory Toxicity:	0.847
Drug-induced Neurotoxicity:	0.081	Ototoxicity:	0.925
Hematotoxicity:	0.064	Drug-induced Nephrotoxicity:	0.94
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.09
A549 Cytotoxicity:	0.957	Hek293 Cytotoxicity:	0.411
BCF:	1.411 ? 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:	4.964 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.16 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.233 ? 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	11
IC50	4

Activity Type	# Activity
Cell line	13
Non-molecular	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
NPT147	Cell line	SK-MEL-2	Homo sapiens	ED50	=	18.0	ug ml-1	DOI[10.6019/CHEMBL1201861]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	6.0	ug ml-1	DOI[10.6019/CHEMBL1201861]
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	14.1	ug ml-1	PMID[17341114]
NPT307	Cell line	HOS	Homo sapiens	ED50	=	18.4	ug ml-1	DOI[10.6019/CHEMBL1201861]
NPT180	Cell line	HCT-8	Homo sapiens	ED50	=	15.0	ug ml-1	PMID[23746784]
NPT308	Cell line	CAKI-1	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[23746784]
NPT81	Cell line	A549	Homo sapiens	ED50	=	16.8	ug ml-1	PMID[23746784]
NPT309	Cell line	1A9	Homo sapiens	ED50	=	0.33	ug ml-1	PMID[17338565]
NPT310	Cell line	1A9/ptx-10	Homo sapiens	ED50	=	8.2	ug ml-1	PMID[17338565]
NPT91	Cell line	KB	Homo sapiens	ED50	=	12.8	ug ml-1	PMID[17338565]
NPT91	Cell line	KB	Homo sapiens	ED50	=	15.0	ug ml-1	PMID[17338565]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	5.04	ug.mL-1	DOI[10.6019/CHEMBL1201861]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	0.00513	ug.mL-1	PMID[11473425]

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 NPC473651 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	17382
0.1-0.2	29776
0.2-0.3	2376
0.3-0.4	95
0.4-0.5	17
0.5-0.6	39
0.6-0.7	60
0.7-0.8	0
0.8-0.85	12
0.85-0.9	7
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473478
1.0	High Similarity	NPC66346
0.9792	High Similarity	NPC283085
0.9388	High Similarity	NPC231096
0.9388	High Similarity	NPC475581
0.9388	High Similarity	NPC62118
0.9388	High Similarity	NPC132496
0.9388	High Similarity	NPC107717
0.9388	High Similarity	NPC488252
0.898	High Similarity	NPC20621
0.898	High Similarity	NPC318963
0.898	High Similarity	NPC605101
0.8846	High Similarity	NPC91067
0.8846	High Similarity	NPC480081
0.8627	High Similarity	NPC606740
0.8627	High Similarity	NPC608614
0.8367	Intermediate Similarity	NPC134865
0.8367	Intermediate Similarity	NPC103523
0.8367	Intermediate Similarity	NPC488627
0.8367	Intermediate Similarity	NPC488631
0.8269	Intermediate Similarity	NPC169511
0.8269	Intermediate Similarity	NPC287164
0.8269	Intermediate Similarity	NPC234077
0.8214	Intermediate Similarity	NPC279267
0.8113	Intermediate Similarity	NPC233551
0.8113	Intermediate Similarity	NPC40376
0.8113	Intermediate Similarity	NPC21208
0.8039	Intermediate Similarity	NPC65930
0.7917	Intermediate Similarity	NPC606043
0.7755	Intermediate Similarity	NPC107986
0.7755	Intermediate Similarity	NPC223871
0.7755	Intermediate Similarity	NPC231009
0.7755	Intermediate Similarity	NPC103284
0.7755	Intermediate Similarity	NPC110710
0.7755	Intermediate Similarity	NPC1083
0.7755	Intermediate Similarity	NPC82795
0.7755	Intermediate Similarity	NPC286338
0.7755	Intermediate Similarity	NPC603931
0.7755	Intermediate Similarity	NPC604237
0.7647	Intermediate Similarity	NPC477011
0.76	Intermediate Similarity	NPC488253
0.76	Intermediate Similarity	NPC473669
0.76	Intermediate Similarity	NPC488251
0.7547	Intermediate Similarity	NPC329615
0.7451	Intermediate Similarity	NPC81045
0.7451	Intermediate Similarity	NPC232555
0.7451	Intermediate Similarity	NPC39754
0.7451	Intermediate Similarity	NPC171135
0.7451	Intermediate Similarity	NPC171174
0.7451	Intermediate Similarity	NPC182383
0.7451	Intermediate Similarity	NPC114694
0.7451	Intermediate Similarity	NPC61257
0.7451	Intermediate Similarity	NPC320569
0.7451	Intermediate Similarity	NPC485248
0.7451	Intermediate Similarity	NPC133730
0.7451	Intermediate Similarity	NPC191929
0.7451	Intermediate Similarity	NPC142117
0.7451	Intermediate Similarity	NPC100454
0.7451	Intermediate Similarity	NPC242364
0.7451	Intermediate Similarity	NPC480249
0.7451	Intermediate Similarity	NPC172821
0.7451	Intermediate Similarity	NPC485249
0.7451	Intermediate Similarity	NPC274446
0.7451	Intermediate Similarity	NPC485251
0.7451	Intermediate Similarity	NPC151403
0.7451	Intermediate Similarity	NPC240695
0.7451	Intermediate Similarity	NPC261952
0.7451	Intermediate Similarity	NPC605171
0.7308	Intermediate Similarity	NPC93794
0.7308	Intermediate Similarity	NPC488632
0.7308	Intermediate Similarity	NPC473504
0.7308	Intermediate Similarity	NPC81778
0.7308	Intermediate Similarity	NPC40066
0.7288	Intermediate Similarity	NPC482766
0.7273	Intermediate Similarity	NPC258068
0.7273	Intermediate Similarity	NPC476583
0.7241	Intermediate Similarity	NPC473663
0.7241	Intermediate Similarity	NPC473723
0.7241	Intermediate Similarity	NPC475173
0.7222	Intermediate Similarity	NPC602738
0.7193	Intermediate Similarity	NPC488630
0.7193	Intermediate Similarity	NPC488625
0.7193	Intermediate Similarity	NPC488626
0.717	Intermediate Similarity	NPC280621
0.717	Intermediate Similarity	NPC48338
0.717	Intermediate Similarity	NPC241360
0.717	Intermediate Similarity	NPC293136
0.717	Intermediate Similarity	NPC488628
0.7143	Intermediate Similarity	NPC480082
0.7069	Intermediate Similarity	NPC253801
0.7037	Intermediate Similarity	NPC178215
0.7037	Intermediate Similarity	NPC42598
0.7037	Intermediate Similarity	NPC473687
0.7037	Intermediate Similarity	NPC204686
0.7037	Intermediate Similarity	NPC219498
0.7037	Intermediate Similarity	NPC308412
0.7037	Intermediate Similarity	NPC134885
0.7037	Intermediate Similarity	NPC488247
0.7037	Intermediate Similarity	NPC210218
0.7037	Intermediate Similarity	NPC488248
0.6981	Remote Similarity	NPC47937
0.6909	Remote Similarity	NPC488250
0.6842	Remote Similarity	NPC488623
0.6842	Remote Similarity	NPC488624
0.6842	Remote Similarity	NPC488629
0.6786	Remote Similarity	NPC69082
0.6786	Remote Similarity	NPC488249
0.6731	Remote Similarity	NPC329829
0.6667	Remote Similarity	NPC112685
0.6667	Remote Similarity	NPC130359
0.6667	Remote Similarity	NPC14901
0.6667	Remote Similarity	NPC608138
0.6607	Remote Similarity	NPC329838
0.6607	Remote Similarity	NPC134807
0.6552	Remote Similarity	NPC320458
0.6545	Remote Similarity	NPC480079
0.6441	Remote Similarity	NPC239517
0.6415	Remote Similarity	NPC100921
0.6415	Remote Similarity	NPC475159
0.6415	Remote Similarity	NPC131002
0.6415	Remote Similarity	NPC473780
0.6415	Remote Similarity	NPC477018
0.6415	Remote Similarity	NPC604521
0.6364	Remote Similarity	NPC488246
0.6364	Remote Similarity	NPC480080
0.6364	Remote Similarity	NPC600524
0.6364	Remote Similarity	NPC608355
0.6333	Remote Similarity	NPC322529
0.6271	Remote Similarity	NPC477014
0.6271	Remote Similarity	NPC477013
0.625	Remote Similarity	NPC219652
0.625	Remote Similarity	NPC473840
0.6207	Remote Similarity	NPC20339
0.6182	Remote Similarity	NPC156804
0.6154	Remote Similarity	NPC73310
0.6154	Remote Similarity	NPC473529
0.6154	Remote Similarity	NPC180363
0.6154	Remote Similarity	NPC94875
0.6154	Remote Similarity	NPC11332
0.6154	Remote Similarity	NPC145914
0.6154	Remote Similarity	NPC601174
0.6154	Remote Similarity	NPC601403
0.6154	Remote Similarity	NPC603568
0.6154	Remote Similarity	NPC604330
0.6154	Remote Similarity	NPC608300
0.6154	Remote Similarity	NPC611200
0.6154	Remote Similarity	NPC611571
0.614	Remote Similarity	NPC473904
0.6102	Remote Similarity	NPC473995
0.6071	Remote Similarity	NPC473649
0.6071	Remote Similarity	NPC473156
0.6071	Remote Similarity	NPC154097
0.6071	Remote Similarity	NPC163093
0.6071	Remote Similarity	NPC159750
0.6071	Remote Similarity	NPC73248
0.6071	Remote Similarity	NPC282815
0.6071	Remote Similarity	NPC470401
0.6071	Remote Similarity	NPC600956
0.6071	Remote Similarity	NPC610454
0.6066	Remote Similarity	NPC473520
0.5965	Remote Similarity	NPC473671
0.5965	Remote Similarity	NPC475268
0.5965	Remote Similarity	NPC470400
0.5965	Remote Similarity	NPC25703
0.5965	Remote Similarity	NPC77871
0.5965	Remote Similarity	NPC9678
0.5965	Remote Similarity	NPC319036
0.5965	Remote Similarity	NPC604764
0.5965	Remote Similarity	NPC605867
0.5932	Remote Similarity	NPC473707
0.5932	Remote Similarity	NPC477012
0.5862	Remote Similarity	NPC132940
0.5833	Remote Similarity	NPC488244
0.5818	Remote Similarity	NPC25764
0.5818	Remote Similarity	NPC235809
0.5818	Remote Similarity	NPC39279
0.5818	Remote Similarity	NPC39167
0.5818	Remote Similarity	NPC292809
0.5818	Remote Similarity	NPC202055
0.5818	Remote Similarity	NPC606804
0.5818	Remote Similarity	NPC607425
0.5818	Remote Similarity	NPC608574
0.5763	Remote Similarity	NPC309211
0.5763	Remote Similarity	NPC20533
0.5763	Remote Similarity	NPC485250
0.5763	Remote Similarity	NPC477010
0.5692	Remote Similarity	NPC477017
0.5692	Remote Similarity	NPC477016
0.5686	Remote Similarity	NPC609415
0.5574	Remote Similarity	NPC120398
0.5574	Remote Similarity	NPC471567
0.5517	Remote Similarity	NPC144415
0.5517	Remote Similarity	NPC607439
0.5517	Remote Similarity	NPC608157
0.5484	Remote Similarity	NPC89001
0.5469	Remote Similarity	NPC473905
0.5469	Remote Similarity	NPC477015
0.5424	Remote Similarity	NPC475616
0.541	Remote Similarity	NPC139418

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6505
0.1-0.2	2596
0.2-0.3	49
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