NPASS Compound

Natural Product: NPC246893

Natural Product ID	NPC246893
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Reticuloside
IUPAC Name	methyl (4S,5E,6S)-5-ethylidene-4-[2-oxo-2-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxyphenoxy]oxan-2-yl]methoxy]ethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
Synonyms	Reticuloside
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1911051
PubChem CID	57390293
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

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 99102 0 0 0 0 0 0 0 0999 V2000 13.4489 1.0955 -0.0551 O 0 0 0 0 0 0 0 0 0 0 0 0 13.0274 0.0759 -0.8967 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5620 -0.2164 -0.7506 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7547 0.4091 0.0727 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3222 0.0534 0.1465 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7341 -0.8988 -0.6448 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3869 -1.1806 -0.5032 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8626 -2.1474 -1.3267 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6052 -2.8603 -2.2771 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5737 -0.5223 0.4355 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1688 0.4298 1.2232 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5329 0.6873 1.0516 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4229 1.1236 2.1715 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0275 2.1092 2.9838 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2870 -0.8475 0.5153 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1215 -0.2871 -0.0606 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1370 -0.3712 0.8344 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9468 0.2269 0.5213 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9740 -0.3157 1.5629 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2919 -0.0328 1.5641 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3030 0.8397 1.6762 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9537 2.0360 1.8965 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7142 0.4433 1.5578 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3960 0.4001 0.2559 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7795 -0.1702 0.4473 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9106 -1.4858 0.4879 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8449 -2.4882 0.3679 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9224 0.7216 0.6048 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8505 1.8139 -0.2995 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6238 2.3035 -0.6747 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4713 1.6887 -0.4432 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2638 2.3711 -0.9696 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1170 1.8947 -0.8857 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3880 3.5906 -1.5778 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3949 4.3951 -2.1212 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1673 0.1195 0.3337 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1063 0.3938 1.2871 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6123 -0.6181 2.0189 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4281 -1.4854 1.3731 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6995 -2.5622 0.5786 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6944 -3.3835 0.0083 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4588 -0.8203 0.5291 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.9794 0.3530 -0.2480 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.2462 1.2557 0.7566 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1544 1.5153 1.7917 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0045 -0.0401 -1.1777 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.5016 -0.4027 1.3742 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5245 -0.0450 -0.8672 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2732 -1.1930 -1.5183 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7447 -1.0801 -1.3220 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3549 -0.3986 -2.3948 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8167 -2.3918 -0.9494 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7570 1.1083 -1.6444 O 0 0 0 0 0 0 0 0 0 0 0 0 14.2330 0.7987 0.4741 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2867 0.3309 -1.9318 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5695 -0.8476 -0.6161 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2169 -1.0261 -1.4104 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1787 1.1895 0.6899 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3409 -1.4180 -1.3761 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5639 -3.2321 -1.8507 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7902 -2.2883 -3.1858 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0513 -3.8022 -2.5437 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9405 1.4620 1.7206 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7061 1.5903 3.6807 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2576 2.7046 3.5387 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6052 2.8047 2.3546 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3615 0.7521 -0.3431 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0606 1.3321 0.6900 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5407 -0.1075 2.5416 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1169 -1.4486 1.4943 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8615 -0.5376 2.1232 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2689 1.1654 2.2506 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8434 -0.3099 -0.4015 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9347 -1.8852 0.6296 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5259 -2.8080 1.4061 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0012 -2.2480 -0.2676 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2644 -3.4502 -0.0706 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9839 1.2412 1.6146 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5761 3.2780 -1.2075 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5399 5.4149 -1.6414 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5015 4.5180 -3.2287 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4204 3.9858 -1.8402 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5769 1.0852 2.0318 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9512 -2.0814 2.2067 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1567 -2.0048 -0.2350 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0532 -3.1105 1.2520 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8178 -4.1779 0.5985 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8830 -1.5790 -0.1679 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7942 0.9067 -0.7026 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9399 2.1882 0.3034 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7695 1.3018 2.6839 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9335 0.7520 -1.7991 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7443 -1.1872 1.9428 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4386 -0.2505 -0.9425 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0566 -1.1658 -2.6277 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1563 -2.1007 -1.1980 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7143 0.3002 -2.7185 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1110 -3.1349 -1.5396 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9566 1.8904 -1.0359 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 2 0 6 7 1 0 7 8 1 0 8 9 1 0 7 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 10 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 2 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 25 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 1 0 28 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 43 46 1 0 42 47 1 0 18 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 49 52 1 0 48 53 1 0 12 5 1 0 50 16 1 0 31 24 1 0 44 37 1 0 1 54 1 0 2 55 1 0 2 56 1 0 3 57 1 0 4 58 1 0 6 59 1 0 9 60 1 0 9 61 1 0 9 62 1 0 12 63 1 0 14 64 1 0 14 65 1 0 14 66 1 0 16 67 1 6 18 68 1 6 19 69 1 0 19 70 1 0 23 71 1 0 23 72 1 0 24 73 1 6 26 74 1 0 27 75 1 0 27 76 1 0 27 77 1 0 28 78 1 1 30 79 1 0 35 80 1 0 35 81 1 0 35 82 1 0 37 83 1 1 39 84 1 1 40 85 1 0 40 86 1 0 41 87 1 0 42 88 1 6 43 89 1 6 44 90 1 6 45 91 1 0 46 92 1 0 47 93 1 0 48 94 1 1 49 95 1 6 50 96 1 1 51 97 1 0 52 98 1 0 53 99 1 0 M END

Standard InCHIKey	UUUCHDSMSNBEBE-FFAJWEQASA-N
Standard InCHI	InChI=1S/C34H46O19/c1-5-16-17(18(31(44)47-4)13-49-32(16)53-34-29(43)26(40)24(38)21(12-36)50-34)11-23(37)48-14-22-25(39)27(41)28(42)33(51-22)52-30-19(45-2)9-15(7-6-8-35)10-20(30)46-3/h5-7,9-10,13,17,21-22,24-29,32-36,38-43H,8,11-12,14H2,1-4H3/b7-6+,16-5+/t17-,21+,22+,24+,25+,26-,27-,28+,29+,32-,33-,34-/m0/s1
SMILES	OC/C=C/c1cc(OC)c(c(c1)OC)O[C@@H]1O[C@H](COC(=O)C[C@H]2/C(=CC)/[C@@H](OC=C2C(=O)OC)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	758.26	Volume:	708.317 ? Van der Waals volume.
Dense:	1.071	LogP:	-0.276 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.39 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.618 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	28.0
TPSA:	279.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	8.0	Rings:	4.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.073	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.448	Fsp³:	0.588
MCE-18:	110.222 ? 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:	0.443	Fluc inhibitor:	0.24 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.114 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.496 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.101	Promiscuous compounds:	0.129

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.83	MDCK Permeability:	-5.193
Pgp-inhibitor:	0.0	Pgp-substrate:	0.649
PAMPA:	0.997 ? 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):	0.198
20% Bioavailability (F20%):	0.35	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.388
Plasma Protein Binding (PPB):	73.501%	Volume Distribution (VD):	-0.315
Fu:	22.762% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.061
BSEP inhibitor:	0.01

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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.116
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.683
HLM stability:	0.308 ? 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):

0.994

Half-life (T1/2):

2.67

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.041
Human Hepatotoxicity (H-HT):	0.941	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.95	Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.085	Skin Sensitization:	1.0
Carcinogencity:	0.104	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.064	Ototoxicity:	0.994
Hematotoxicity:	0.46	Drug-induced Nephrotoxicity:	0.964
Genotoxicity:	0.988	RPMI-8226 Immunitoxicity:	0.473
A549 Cytotoxicity:	0.746	Hek293 Cytotoxicity:	0.216
BCF:	0.358 ? 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:	3.044 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.161 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.033 ? 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
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21955940]
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16259	Syringa reticulata	Species	Oleaceae	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
EC50	2

Activity Type	# Activity
Others	1
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	64140.0	nM	PMID[21955940]
NPT1	Others	Radical scavenging activity	n.a.	EC50	>	100000.0	nM	PMID[22037378]

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 NPC246893 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	11341
0.1-0.2	33678
0.2-0.3	4079
0.3-0.4	679
0.4-0.5	58
0.5-0.6	13
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8652	High Similarity	NPC488385
0.7253	Intermediate Similarity	NPC488388
0.6421	Remote Similarity	NPC488384
0.6207	Remote Similarity	NPC469543
0.6186	Remote Similarity	NPC488383
0.6105	Remote Similarity	NPC600692
0.6061	Remote Similarity	NPC23677
0.6	Remote Similarity	NPC65262
0.6	Remote Similarity	NPC84429
0.6	Remote Similarity	NPC101686
0.5941	Remote Similarity	NPC198577
0.5904	Remote Similarity	NPC303451
0.5904	Remote Similarity	NPC72358
0.5743	Remote Similarity	NPC469364
0.5743	Remote Similarity	NPC609284
0.5567	Remote Similarity	NPC169398
0.551	Remote Similarity	NPC296643
0.551	Remote Similarity	NPC299576
0.5455	Remote Similarity	NPC488387
0.5422	Remote Similarity	NPC49074
0.5405	Remote Similarity	NPC488386
0.5222	Remote Similarity	NPC164857
0.5056	Remote Similarity	NPC470236

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC246893 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4554
0.1-0.2	4502
0.2-0.3	88
0.3-0.4	6
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