NPASS Compound

Natural Product: NPC20533

Natural Product ID	NPC20533
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Salzmanin
IUPAC Name	(2S)-4-[(10R,13R)-13-[(2R,5R)-5-[(2S,5R)-5-[(1S,5S)-1,5-dihydroxyundecyl]oxolan-2-yl]oxolan-2-yl]-10,13-dihydroxytridecyl]-2-methyl-2H-furan-5-one
Synonyms	Salzmanin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL507402
PubChem CID	44566356
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 -13.5110 -0.9856 -0.9051 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.2743 0.2312 -0.0478 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2738 1.1442 -0.7288 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9484 0.4850 -0.9593 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2970 0.0399 0.3309 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9760 -0.6203 0.1069 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3103 -1.0680 1.3868 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0691 0.1213 2.2899 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4219 -0.1688 3.5716 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1440 -0.8334 3.7200 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8486 -0.4006 3.2304 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6129 -0.2775 1.7832 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1880 0.8916 1.0659 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0595 1.3861 0.1481 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1531 0.1591 0.2284 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8216 0.5075 -0.3397 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1951 1.7526 0.2370 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2451 1.5776 -0.1860 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3236 0.1725 -0.6216 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5886 -0.0943 -2.0584 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6992 0.6464 -2.6872 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0585 0.3743 -2.0129 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1412 1.1339 -2.6846 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5198 0.8715 -2.0401 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5274 1.2785 -0.6121 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7753 1.2131 0.1314 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5330 -0.0028 0.4092 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0767 -0.7556 -0.7317 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9284 -1.9438 -0.2247 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4946 -2.7069 -1.3511 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4415 -2.0385 -2.2702 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7285 -1.5573 -1.7423 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7478 -0.5106 -0.7232 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2348 -0.6541 0.4985 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0960 0.5821 1.2513 C 0 0 2 0 0 0 0 0 0 0 0 0 11.2571 0.4265 2.5044 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5529 1.5044 0.3545 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2995 0.8818 -0.8439 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7705 1.4035 -1.8927 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2788 0.6933 -4.0148 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7374 -1.4663 -2.2468 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8393 -0.4332 -0.1571 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1940 -0.0656 1.5781 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5131 0.8643 3.8019 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0930 -2.0328 1.9752 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.1031 -0.7869 -1.9201 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0570 -1.8846 -0.4552 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.6166 -1.1950 -0.9688 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.2259 0.7740 0.0725 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8991 -0.0306 0.9582 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6979 1.4118 -1.7168 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1882 2.0835 -0.1367 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0976 -0.3540 -1.6582 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3086 1.2274 -1.4907 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2268 0.9685 0.9651 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9748 -0.6771 0.8323 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2668 0.0711 -0.3998 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1382 -1.4743 -0.5667 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3427 -1.5432 1.1097 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8051 1.0289 1.7503 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1827 0.3879 2.6026 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1838 -0.8073 4.1668 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4698 0.7972 4.1997 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3357 -1.9432 3.4083 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0586 -1.0467 4.8780 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0174 -1.1179 3.6650 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7744 -1.2452 1.2203 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4980 1.6598 1.7719 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0132 0.5248 0.3897 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4475 1.4802 -0.8621 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5577 2.2566 0.5665 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5561 -0.6959 -0.3103 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9728 0.6038 -1.4498 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6433 2.6764 -0.1289 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3282 1.7150 1.3372 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5933 2.3372 -0.9001 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8536 1.7387 0.7398 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1531 -0.3348 -0.0365 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3723 0.1549 -2.6051 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6002 1.7319 -2.7112 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8392 0.3116 -3.7371 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3030 -0.6915 -1.9919 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9945 0.7153 -0.9429 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9277 2.2097 -2.6225 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7028 -0.2366 -2.1361 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3044 1.4157 -2.5798 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1788 2.3713 -0.5736 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7124 0.7132 -0.0476 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4755 2.0090 -0.3665 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6100 1.7708 1.1330 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9072 -0.7475 1.0231 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4281 0.2140 1.0933 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6826 -0.1712 -1.4040 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2969 -1.2895 -1.3334 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1470 -2.6141 0.2579 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5892 -1.6631 0.5853 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8777 -3.7188 -1.0081 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6072 -3.0161 -2.0010 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6934 -2.8085 -3.0705 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8777 -1.2665 -2.8548 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2786 -2.4674 -1.3338 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3880 -1.2778 -2.6301 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6858 -1.5705 0.9083 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0979 1.0030 1.5519 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7586 1.3453 2.8188 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6035 -0.4472 2.3770 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9891 0.1363 3.3123 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5466 1.0967 -4.5535 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3752 -1.8208 -1.5705 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0418 1.0146 4.6231 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9885 -1.7711 2.2358 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 38 39 2 0 23 40 1 0 20 41 1 0 19 42 1 0 15 43 1 0 11 44 1 0 7 45 1 0 43 12 1 0 42 16 1 0 38 33 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 6 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 1 12 67 1 6 13 68 1 0 13 69 1 0 14 70 1 0 14 71 1 0 15 72 1 6 16 73 1 6 17 74 1 0 17 75 1 0 18 76 1 0 18 77 1 0 19 78 1 1 20 79 1 6 21 80 1 0 21 81 1 0 22 82 1 0 22 83 1 0 23 84 1 6 24 85 1 0 24 86 1 0 25 87 1 0 25 88 1 0 26 89 1 0 26 90 1 0 27 91 1 0 27 92 1 0 28 93 1 0 28 94 1 0 29 95 1 0 29 96 1 0 30 97 1 0 30 98 1 0 31 99 1 0 31100 1 0 32101 1 0 32102 1 0 34103 1 0 35104 1 1 36105 1 0 36106 1 0 36107 1 0 40108 1 0 41109 1 0 44110 1 0 45111 1 0 M END

Standard InCHIKey	PRWFLCNEESBSRN-ZETXPVFNSA-N
Standard InCHI	InChI=1S/C37H66O8/c1-3-4-5-12-16-29(38)18-14-19-31(40)33-22-24-35(44-33)36-25-23-34(45-36)32(41)21-20-30(39)17-13-10-8-6-7-9-11-15-28-26-27(2)43-37(28)42/h26-27,29-36,38-41H,3-25H2,1-2H3/t27-,29-,30+,31-,32+,33+,34+,35-,36+/m0/s1
SMILES	CCCCCC[C@@H](CCC[C@@H]([C@H]1CC[C@@H]([C@H]2CC[C@H]([C@@H](CC[C@@H](CCCCCCCCCC3=C[C@H](C)OC3=O)O)O)O2)O1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.48	Volume:	687.887 ? Van der Waals volume.
Dense:	0.928	LogP:	3.844 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.185 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.25 ? 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:	4.973	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:	0.878	Fluc inhibitor:	0.03 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.086 ? 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:	0.588	Promiscuous compounds:	0.387

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.182	MDCK Permeability:	-4.754
Pgp-inhibitor:	0.017	Pgp-substrate:	0.999
PAMPA:	0.449 ? 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):	0.0
20% Bioavailability (F20%):	0.846	30% Bioavailability (F30%):	0.989
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.455
Plasma Protein Binding (PPB):	91.234%	Volume Distribution (VD):	0.103
Fu:	7.287% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.357
OATP1B3 inhibitor:	0.553	BCRP inhibitor:	0.884
BSEP inhibitor:	0.955

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.048
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.01
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.469
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.993
HLM stability:	0.032 ? 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):

6.418

Half-life (T1/2):

1.06

ADMET: Toxicity

hERG Blockers:	0.635	hERG Blockers (10um):	0.886
Human Hepatotoxicity (H-HT):	0.777	Drug-induced Liver Injury (DILI):	0.057
AMES Toxicity:	0.324	Rat Oral Acute Toxicity:	0.124
Maximum Recommended Daily Dose:	0.968	Skin Sensitization:	1.0
Carcinogencity:	0.364	Eye Corrosion:	0.054
Eye Irritation:	0.475	Respiratory Toxicity:	0.992
Drug-induced Neurotoxicity:	0.089	Ototoxicity:	0.878
Hematotoxicity:	0.192	Drug-induced Nephrotoxicity:	0.989
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.114
A549 Cytotoxicity:	0.998	Hek293 Cytotoxicity:	0.569
BCF:	1.373 ? 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:	5.234 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.369 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.968 ? 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
NPO33069	annona salzmanii	Species	Annonaceae	Eukaryota	roots	n.a.	n.a.	PMID[10346951]
NPO33069	annona salzmanii	Species	Annonaceae	Eukaryota	roots	n.a.	n.a.	PMID[12828457]

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	2

Activity Type	# Activity
Cell line	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
NPT91	Cell line	KB	Homo sapiens	ED50	=	0.1	10'-4 ug/ml	PMID[10843574]
NPT189	Cell line	Vero	Chlorocebus aethiops	ED50	>	0.01	ug ml-1	PMID[10843574]

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 NPC20533 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	16966
0.1-0.2	29913
0.2-0.3	2672
0.3-0.4	72
0.4-0.5	37
0.5-0.6	47
0.6-0.7	51
0.7-0.8	0
0.8-0.85	10
0.85-0.9	17
0.9-0.95	3
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9783	High Similarity	NPC132940
0.9565	High Similarity	NPC473671
0.9565	High Similarity	NPC475268
0.9565	High Similarity	NPC470400
0.9565	High Similarity	NPC77871
0.9565	High Similarity	NPC9678
0.9565	High Similarity	NPC319036
0.9565	High Similarity	NPC605867
0.9348	High Similarity	NPC473156
0.9348	High Similarity	NPC282815
0.9348	High Similarity	NPC600956
0.8936	High Similarity	NPC610454
0.875	High Similarity	NPC604764
0.8723	High Similarity	NPC156804
0.8696	High Similarity	NPC25764
0.8696	High Similarity	NPC235809
0.8696	High Similarity	NPC39279
0.8696	High Similarity	NPC39167
0.8696	High Similarity	NPC292809
0.8696	High Similarity	NPC202055
0.8696	High Similarity	NPC606804
0.8696	High Similarity	NPC607425
0.8696	High Similarity	NPC608574
0.8542	High Similarity	NPC473649
0.8542	High Similarity	NPC154097
0.8542	High Similarity	NPC159750
0.8542	High Similarity	NPC73248
0.8542	High Similarity	NPC470401
0.8367	Intermediate Similarity	NPC219652
0.8367	Intermediate Similarity	NPC473840
0.8298	Intermediate Similarity	NPC475159
0.8298	Intermediate Similarity	NPC131002
0.8298	Intermediate Similarity	NPC473780
0.8298	Intermediate Similarity	NPC604521
0.82	Intermediate Similarity	NPC42598
0.8077	Intermediate Similarity	NPC120398
0.8077	Intermediate Similarity	NPC471567
0.8039	Intermediate Similarity	NPC329838
0.78	Intermediate Similarity	NPC93794
0.78	Intermediate Similarity	NPC473504
0.78	Intermediate Similarity	NPC81778
0.78	Intermediate Similarity	NPC40066
0.7736	Intermediate Similarity	NPC258068
0.7736	Intermediate Similarity	NPC476583
0.7692	Intermediate Similarity	NPC485250
0.7692	Intermediate Similarity	NPC605396
0.766	Intermediate Similarity	NPC73310
0.766	Intermediate Similarity	NPC473529
0.766	Intermediate Similarity	NPC180363
0.766	Intermediate Similarity	NPC94875
0.766	Intermediate Similarity	NPC11332
0.766	Intermediate Similarity	NPC145914
0.766	Intermediate Similarity	NPC601174
0.766	Intermediate Similarity	NPC601403
0.766	Intermediate Similarity	NPC603568
0.766	Intermediate Similarity	NPC604330
0.766	Intermediate Similarity	NPC608300
0.766	Intermediate Similarity	NPC611200
0.766	Intermediate Similarity	NPC611571
0.7647	Intermediate Similarity	NPC25703
0.76	Intermediate Similarity	NPC81045
0.76	Intermediate Similarity	NPC39754
0.76	Intermediate Similarity	NPC171135
0.76	Intermediate Similarity	NPC61257
0.76	Intermediate Similarity	NPC320569
0.76	Intermediate Similarity	NPC133730
0.76	Intermediate Similarity	NPC191929
0.76	Intermediate Similarity	NPC100454
0.76	Intermediate Similarity	NPC242364
0.76	Intermediate Similarity	NPC172821
0.76	Intermediate Similarity	NPC274446
0.76	Intermediate Similarity	NPC485251
0.76	Intermediate Similarity	NPC151403
0.76	Intermediate Similarity	NPC261952
0.76	Intermediate Similarity	NPC605171
0.7593	Intermediate Similarity	NPC89001
0.7551	Intermediate Similarity	NPC100921
0.7551	Intermediate Similarity	NPC477018
0.7451	Intermediate Similarity	NPC488632
0.7451	Intermediate Similarity	NPC163093
0.7451	Intermediate Similarity	NPC600524
0.7451	Intermediate Similarity	NPC608355
0.7407	Intermediate Similarity	NPC473995
0.7255	Intermediate Similarity	NPC232555
0.7255	Intermediate Similarity	NPC171174
0.7255	Intermediate Similarity	NPC114694
0.7255	Intermediate Similarity	NPC485248
0.7255	Intermediate Similarity	NPC142117
0.7255	Intermediate Similarity	NPC480249
0.7255	Intermediate Similarity	NPC485249
0.7255	Intermediate Similarity	NPC240695
0.72	Intermediate Similarity	NPC329829
0.7193	Intermediate Similarity	NPC473905
0.7059	Intermediate Similarity	NPC488253
0.7059	Intermediate Similarity	NPC473669
0.7059	Intermediate Similarity	NPC488251
0.7037	Intermediate Similarity	NPC602738
0.7018	Intermediate Similarity	NPC473520
0.6981	Remote Similarity	NPC241360
0.6981	Remote Similarity	NPC293136
0.6964	Remote Similarity	NPC477014
0.6964	Remote Similarity	NPC477013
0.6863	Remote Similarity	NPC107986
0.6863	Remote Similarity	NPC223871
0.6863	Remote Similarity	NPC231009
0.6863	Remote Similarity	NPC103284
0.6863	Remote Similarity	NPC110710
0.6863	Remote Similarity	NPC1083
0.6863	Remote Similarity	NPC82795
0.6863	Remote Similarity	NPC286338
0.6863	Remote Similarity	NPC603931
0.6863	Remote Similarity	NPC604237
0.6792	Remote Similarity	NPC144415
0.6792	Remote Similarity	NPC477011
0.6792	Remote Similarity	NPC607439
0.6792	Remote Similarity	NPC608157
0.6786	Remote Similarity	NPC169511
0.6786	Remote Similarity	NPC287164
0.6786	Remote Similarity	NPC234077
0.6727	Remote Similarity	NPC309211
0.6727	Remote Similarity	NPC477010
0.6667	Remote Similarity	NPC280621
0.6667	Remote Similarity	NPC48338
0.6667	Remote Similarity	NPC488628
0.6667	Remote Similarity	NPC606043
0.6552	Remote Similarity	NPC239517
0.6545	Remote Similarity	NPC178215
0.6545	Remote Similarity	NPC65930
0.6481	Remote Similarity	NPC134865
0.6481	Remote Similarity	NPC103523
0.6481	Remote Similarity	NPC488627
0.6481	Remote Similarity	NPC47937
0.6481	Remote Similarity	NPC488631
0.6441	Remote Similarity	NPC91067
0.6441	Remote Similarity	NPC280612
0.6429	Remote Similarity	NPC329615
0.6316	Remote Similarity	NPC69082
0.6316	Remote Similarity	NPC488249
0.6296	Remote Similarity	NPC182383
0.623	Remote Similarity	NPC473663
0.623	Remote Similarity	NPC473723
0.623	Remote Similarity	NPC475173
0.614	Remote Similarity	NPC20621
0.614	Remote Similarity	NPC318963
0.614	Remote Similarity	NPC488250
0.614	Remote Similarity	NPC605101
0.6122	Remote Similarity	NPC609415
0.6034	Remote Similarity	NPC20339
0.6034	Remote Similarity	NPC477012
0.5965	Remote Similarity	NPC473687
0.5965	Remote Similarity	NPC204686
0.5965	Remote Similarity	NPC219498
0.5965	Remote Similarity	NPC308412
0.5965	Remote Similarity	NPC134885
0.5965	Remote Similarity	NPC488247
0.5965	Remote Similarity	NPC210218
0.5965	Remote Similarity	NPC488248
0.5833	Remote Similarity	NPC488623
0.5833	Remote Similarity	NPC320458
0.5833	Remote Similarity	NPC488624
0.5833	Remote Similarity	NPC480082
0.5833	Remote Similarity	NPC488629
0.5806	Remote Similarity	NPC253801
0.5806	Remote Similarity	NPC477015
0.58	Remote Similarity	NPC608138
0.5789	Remote Similarity	NPC480079
0.5781	Remote Similarity	NPC477017
0.5781	Remote Similarity	NPC477016
0.5763	Remote Similarity	NPC473478
0.5763	Remote Similarity	NPC473651
0.5763	Remote Similarity	NPC66346
0.5667	Remote Similarity	NPC231096
0.5667	Remote Similarity	NPC475581
0.5667	Remote Similarity	NPC283085
0.5667	Remote Similarity	NPC62118
0.5667	Remote Similarity	NPC132496
0.5667	Remote Similarity	NPC107717
0.5667	Remote Similarity	NPC130359
0.5667	Remote Similarity	NPC488252
0.5667	Remote Similarity	NPC14901
0.5667	Remote Similarity	NPC606740
0.5667	Remote Similarity	NPC608614
0.5645	Remote Similarity	NPC322529
0.5593	Remote Similarity	NPC134807
0.5574	Remote Similarity	NPC233551
0.5574	Remote Similarity	NPC40376
0.5574	Remote Similarity	NPC21208
0.5556	Remote Similarity	NPC112685
0.55	Remote Similarity	NPC473707
0.5455	Remote Similarity	NPC480072
0.5397	Remote Similarity	NPC488630
0.5397	Remote Similarity	NPC488625
0.5397	Remote Similarity	NPC488626
0.5246	Remote Similarity	NPC480076
0.5246	Remote Similarity	NPC480077
0.5156	Remote Similarity	NPC480081

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC20533 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6586
0.1-0.2	2511
0.2-0.3	53
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