NPASS Compound

Natural Product: NPC592857

Natural Product ID	NPC592857
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-6-[[(2~{R},3~{R},4~{R},5~{R},6~{S})-3,4-dihydroxy-6-methyl-5-[(2~{S},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxymethyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-7-methoxy-chromen-4-one
IUPAC Name	3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-6-[[(2~{R},3~{R},4~{R},5~{R},6~{S})-3,4-dihydroxy-6-methyl-5-[(2~{S},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxymethyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-7-methoxy-chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 99104 0 0 0 0 0 0 0 0999 V2000 -5.7310 5.0337 3.7517 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1582 3.9897 2.9442 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3651 3.0946 2.2595 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9861 3.1392 2.3055 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2140 2.2222 1.6025 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8284 2.2672 1.6491 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8354 1.2408 0.8378 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1232 0.3099 0.1278 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8691 0.3297 0.1549 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7858 -0.6661 -0.6306 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9769 -1.5412 -1.2835 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4634 -2.7166 -0.6411 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2204 -2.2750 -0.1303 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1455 -3.0115 -0.5268 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1175 -2.2237 -0.1351 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1070 -0.9963 -0.7669 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2295 -0.2335 -0.4597 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8312 0.9472 0.1063 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8418 1.7511 0.5405 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0575 1.6574 2.0396 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1129 1.4675 -0.2100 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0019 2.5168 -0.0284 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2552 2.0904 0.4180 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6217 2.6572 1.6371 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6533 1.8866 2.1744 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2412 0.4428 2.3991 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8600 1.8570 1.2624 C 0 0 2 0 0 0 0 0 0 0 0 0 9.9352 2.4005 1.9627 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6516 2.6914 0.0226 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8711 4.0414 0.3024 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2917 2.4621 -0.5942 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3235 1.4830 -1.5800 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7350 1.3146 -1.6926 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8285 2.3134 -2.0322 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9904 -0.0150 -1.7597 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9513 -1.0153 -1.8478 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0190 -3.2586 -1.9969 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6965 -4.4523 -2.1729 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3640 -3.3959 -2.7037 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7574 -2.1177 -3.0932 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3282 -3.8274 -1.5866 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7646 -4.9829 -1.0012 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1350 -0.6569 -0.6416 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9109 -1.6106 -1.3936 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4637 -2.4066 -2.3990 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3135 -3.3369 -3.0223 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6232 -3.4827 -2.6493 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4668 -4.4185 -3.2805 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0933 -2.6810 -1.6316 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4122 -2.7989 -1.2271 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8869 -1.9810 -0.1890 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2528 -1.7801 -1.0340 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8121 0.2768 0.0741 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2038 1.1793 0.7784 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9698 2.0965 1.4821 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4938 5.8651 3.7329 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6577 4.7317 4.8371 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7592 5.4129 3.3876 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5173 3.9046 2.9035 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4068 2.9157 2.2995 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0999 -2.9808 0.2198 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0376 -3.9567 0.0900 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0212 -2.7674 -0.4883 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1211 -2.0870 0.9713 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8554 -0.8574 0.2366 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5349 2.8157 0.2952 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7964 2.4751 2.2910 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1605 1.8478 2.6207 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5579 0.7135 2.3154 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5540 0.4878 0.0566 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1957 0.9815 0.4876 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8781 2.3137 3.1755 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1733 0.3305 2.6441 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8906 0.0538 3.2373 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5391 -0.1986 1.5166 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1580 0.8221 0.9748 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7968 1.9786 1.6533 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4072 2.3877 -0.7281 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6085 4.1858 0.9209 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0165 3.4486 -1.0664 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2539 1.9092 -2.4543 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5893 1.3736 -2.3598 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0866 3.1943 -1.6372 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3261 -0.1033 -2.6296 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5931 -1.8356 -2.2719 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5376 -2.4634 -2.5362 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8100 -4.5868 -3.1590 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3376 -4.1109 -3.5263 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9720 -1.5551 -3.3251 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2676 -4.1476 -2.0258 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2245 -5.1333 -0.1378 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4492 -2.3038 -2.7516 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9097 -3.9579 -3.8267 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2064 -4.0881 -3.9195 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8579 -0.8846 -0.4477 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9672 -2.1967 0.0153 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3552 -2.0920 0.7537 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6373 -1.1665 -0.2410 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0304 2.0466 1.4348 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 5 7 2 0 7 8 1 0 8 9 2 0 8 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 25 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 21 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 14 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 10 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 47 49 1 0 49 50 1 0 50 51 1 0 49 52 2 0 43 53 1 0 53 54 1 0 54 55 2 0 55 3 1 0 54 7 1 0 41 12 1 0 52 44 1 0 35 17 1 0 31 23 1 0 1 56 1 0 1 57 1 0 1 58 1 0 4 59 1 0 6 60 1 0 12 61 1 1 14 62 1 1 15 63 1 0 15 64 1 0 17 65 1 1 19 66 1 1 20 67 1 0 20 68 1 0 20 69 1 0 21 70 1 1 23 71 1 1 25 72 1 1 26 73 1 0 26 74 1 0 26 75 1 0 27 76 1 6 28 77 1 0 29 78 1 6 30 79 1 0 31 80 1 6 32 81 1 0 33 82 1 6 34 83 1 0 35 84 1 6 36 85 1 0 37 86 1 6 38 87 1 0 39 88 1 6 40 89 1 0 41 90 1 6 42 91 1 0 45 92 1 0 46 93 1 0 48 94 1 0 51 95 1 0 51 96 1 0 51 97 1 0 52 98 1 0 55 99 1 0 M END

Standard InCHIKey	RKDYSYBFDLUFOO-HNGXFMMISA-N
Standard InCHI	InChI=1S/C35H44O20/c1-11-21(38)24(41)27(44)34(50-11)54-30-12(2)51-33(29(46)26(30)43)49-10-19-22(39)25(42)28(45)35(53-19)55-32-23(40)20-16(37)8-14(47-3)9-18(20)52-31(32)13-5-6-15(36)17(7-13)48-4/h5-9,11-12,19,21-22,24-30,33-39,41-46H,10H2,1-4H3/t11-,12-,19+,21-,22+,24-,25-,26+,27+,28+,29+,30-,33+,34-,35-/m0/s1
SMILES	COC1=CC(O)=C2C(=O)C(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O[C@@H]5O[C@@H](C)[C@H](O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)=C(C3=CC=C(O)C(OC)=C3)OC2=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	784.24	Volume:	717.29 ? Van der Waals volume.
Dense:	1.093	LogP:	0.71 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.394 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.986 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	36.0
TPSA:	306.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	10.0	Rings:	6.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.104	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.36	Fsp³:	0.571
MCE-18:	152.455 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.617	Fluc inhibitor:	0.297 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.729 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.424 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.079	Promiscuous compounds:	0.42

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.381	MDCK Permeability:	-5.323
Pgp-inhibitor:	0.0	Pgp-substrate:	0.812
PAMPA:	0.999 ? 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):	0.929
20% Bioavailability (F20%):	0.026	30% Bioavailability (F30%):	0.937
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.021
Plasma Protein Binding (PPB):	77.256%	Volume Distribution (VD):	-0.249
Fu:	21.697% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.921
BSEP inhibitor:	0.003

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.228
HLM stability:	0.737 ? 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):

0.775

Half-life (T1/2):

4.38

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.081
Human Hepatotoxicity (H-HT):	0.451	Drug-induced Liver Injury (DILI):	0.982
AMES Toxicity:	0.973	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.008	Skin Sensitization:	0.999
Carcinogencity:	0.025	Eye Corrosion:	0.0
Eye Irritation:	0.021	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.985
Hematotoxicity:	0.239	Drug-induced Nephrotoxicity:	0.532
Genotoxicity:	0.445	RPMI-8226 Immunitoxicity:	0.336
A549 Cytotoxicity:	0.859	Hek293 Cytotoxicity:	0.663
BCF:	0.436 ? 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:	3.143 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.677 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.869 ? 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
NPO13072	Rhamnus formosana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13072	Rhamnus formosana	Species	Rhamnaceae	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

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

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 NPC592857 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	22564
0.1-0.2	23708
0.2-0.3	2746
0.3-0.4	420
0.4-0.5	279
0.5-0.6	90
0.6-0.7	40
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7551	Intermediate Similarity	NPC476472
0.7551	Intermediate Similarity	NPC294815
0.7551	Intermediate Similarity	NPC16194
0.7396	Intermediate Similarity	NPC186816
0.6733	Remote Similarity	NPC470443
0.6602	Remote Similarity	NPC142142
0.6471	Remote Similarity	NPC126784
0.6471	Remote Similarity	NPC241423
0.6449	Remote Similarity	NPC89052
0.6421	Remote Similarity	NPC46420
0.6421	Remote Similarity	NPC271692
0.6373	Remote Similarity	NPC473571
0.6373	Remote Similarity	NPC110941
0.6346	Remote Similarity	NPC209296
0.6346	Remote Similarity	NPC473327
0.6337	Remote Similarity	NPC173582
0.6337	Remote Similarity	NPC265885
0.6337	Remote Similarity	NPC181465
0.6337	Remote Similarity	NPC215710
0.6337	Remote Similarity	NPC67105
0.6337	Remote Similarity	NPC473438
0.6337	Remote Similarity	NPC253788
0.6311	Remote Similarity	NPC153755
0.6275	Remote Similarity	NPC203259
0.6275	Remote Similarity	NPC33054
0.6275	Remote Similarity	NPC210073
0.6275	Remote Similarity	NPC176740
0.6275	Remote Similarity	NPC471725
0.6275	Remote Similarity	NPC134532
0.6275	Remote Similarity	NPC602582
0.6273	Remote Similarity	NPC480441
0.6273	Remote Similarity	NPC25523
0.6262	Remote Similarity	NPC470446
0.6182	Remote Similarity	NPC173837
0.6176	Remote Similarity	NPC44931
0.6168	Remote Similarity	NPC470449
0.6162	Remote Similarity	NPC223747
0.6122	Remote Similarity	NPC611303
0.6117	Remote Similarity	NPC22062
0.6117	Remote Similarity	NPC473634
0.6117	Remote Similarity	NPC138811
0.6075	Remote Similarity	NPC473073
0.6042	Remote Similarity	NPC249281
0.6	Remote Similarity	NPC121703
0.5981	Remote Similarity	NPC488089
0.5979	Remote Similarity	NPC158674
0.5962	Remote Similarity	NPC65563
0.5962	Remote Similarity	NPC470949
0.5941	Remote Similarity	NPC276377
0.5865	Remote Similarity	NPC39834
0.5865	Remote Similarity	NPC227508
0.5714	Remote Similarity	NPC209550
0.5701	Remote Similarity	NPC488073
0.5701	Remote Similarity	NPC240306
0.5688	Remote Similarity	NPC486577
0.5686	Remote Similarity	NPC116458
0.5686	Remote Similarity	NPC246943
0.5686	Remote Similarity	NPC605784
0.5667	Remote Similarity	NPC192539
0.566	Remote Similarity	NPC150164
0.5636	Remote Similarity	NPC471669
0.5625	Remote Similarity	NPC14187
0.5596	Remote Similarity	NPC32641
0.5596	Remote Similarity	NPC256188
0.5596	Remote Similarity	NPC606657
0.5565	Remote Similarity	NPC217520
0.5556	Remote Similarity	NPC488074
0.5537	Remote Similarity	NPC175429
0.5524	Remote Similarity	NPC251417
0.5517	Remote Similarity	NPC277532
0.5514	Remote Similarity	NPC303913
0.5514	Remote Similarity	NPC156869
0.5495	Remote Similarity	NPC220173
0.5481	Remote Similarity	NPC203050
0.5481	Remote Similarity	NPC488072
0.5481	Remote Similarity	NPC225434
0.5472	Remote Similarity	NPC471079
0.547	Remote Similarity	NPC139571
0.5455	Remote Similarity	NPC138990
0.5455	Remote Similarity	NPC72016
0.5455	Remote Similarity	NPC35119
0.5421	Remote Similarity	NPC67326
0.5391	Remote Similarity	NPC189564
0.5385	Remote Similarity	NPC78326
0.5364	Remote Similarity	NPC12013
0.5364	Remote Similarity	NPC11432
0.5364	Remote Similarity	NPC483415
0.5364	Remote Similarity	NPC477613
0.5357	Remote Similarity	NPC195257
0.5347	Remote Similarity	NPC297987
0.5347	Remote Similarity	NPC136042
0.5345	Remote Similarity	NPC292019
0.5345	Remote Similarity	NPC202908
0.5327	Remote Similarity	NPC609888
0.5321	Remote Similarity	NPC204693
0.5315	Remote Similarity	NPC122467
0.531	Remote Similarity	NPC470445
0.5304	Remote Similarity	NPC203145
0.5294	Remote Similarity	NPC84362
0.5294	Remote Similarity	NPC27640
0.5288	Remote Similarity	NPC101026
0.5288	Remote Similarity	NPC488077
0.5263	Remote Similarity	NPC135358
0.5259	Remote Similarity	NPC473072
0.5259	Remote Similarity	NPC470451
0.5246	Remote Similarity	NPC488079
0.5243	Remote Similarity	NPC59534
0.5238	Remote Similarity	NPC311830
0.5229	Remote Similarity	NPC605592
0.5221	Remote Similarity	NPC470447
0.521	Remote Similarity	NPC488087
0.5189	Remote Similarity	NPC601586
0.5185	Remote Similarity	NPC139320
0.5179	Remote Similarity	NPC473623
0.5175	Remote Similarity	NPC101636
0.5172	Remote Similarity	NPC11468
0.5146	Remote Similarity	NPC305811
0.514	Remote Similarity	NPC116864
0.514	Remote Similarity	NPC244776
0.5138	Remote Similarity	NPC471748
0.5138	Remote Similarity	NPC275454
0.5135	Remote Similarity	NPC475366
0.513	Remote Similarity	NPC602448
0.5098	Remote Similarity	NPC289667
0.5098	Remote Similarity	NPC238376
0.5089	Remote Similarity	NPC65711
0.5088	Remote Similarity	NPC89127
0.5086	Remote Similarity	NPC470455
0.5083	Remote Similarity	NPC488083
0.5082	Remote Similarity	NPC198199
0.5048	Remote Similarity	NPC219904
0.5046	Remote Similarity	NPC187379
0.5043	Remote Similarity	NPC221342
0.5043	Remote Similarity	NPC476470

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC592857 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5867
0.1-0.2	3236
0.2-0.3	39
0.3-0.4	2
0.4-0.5	1
0.5-0.6	1
0.6-0.7	3
0.7-0.8	1
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
0.703	Intermediate Similarity	NPD7251	Phase 2
0.6762	Remote Similarity	NPD7808	Phase 3
0.6346	Remote Similarity	NPD7054	Phase 4
0.6275	Remote Similarity	NPD6797	Phase 2
0.5304	Remote Similarity	NPD7472	Pre-clinical

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