NPASS Compound

Natural Product: NPC263829

Natural Product ID	NPC263829
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ligupurpuroside B
IUPAC Name	[(2R,3R,4R,5R,6R)-4-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL443461
PubChem CID	10101498
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

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 98102 0 0 0 0 0 0 0 0999 V2000 6.4350 1.3192 -3.4055 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5824 0.8764 -1.9643 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0645 0.7604 -1.6240 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1808 0.8741 -0.1249 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9089 0.2771 0.4606 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7360 1.1647 0.1314 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0313 1.7943 -1.0788 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5563 0.4879 -0.0210 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5333 0.9123 0.8121 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2800 1.2953 0.0553 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3867 2.6579 -0.5894 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1192 1.1379 0.7778 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7582 -0.1600 1.0281 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9887 -1.0394 1.0704 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1679 -0.2938 1.6810 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7453 0.1868 2.9080 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7968 -2.2061 1.8070 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1757 -0.5672 0.1029 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3584 -1.0098 0.6714 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7282 -2.4194 0.2519 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9018 -2.8257 1.1419 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1904 -4.1388 0.8299 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0793 -5.0158 1.8826 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4371 -6.4007 1.3287 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8410 -6.3345 0.8057 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8595 -6.6399 1.6816 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1510 -6.5852 1.2226 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4404 -6.2341 -0.0841 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3929 -5.9393 -0.9163 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0718 -5.9775 -0.5094 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7777 -6.1883 -0.5209 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9652 -1.9909 0.8086 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6934 -0.6837 1.1831 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9047 0.1934 1.1293 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4606 0.2696 -0.1240 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5625 -0.1581 0.3045 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3568 1.2068 0.4602 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5303 2.0225 -0.6744 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8589 1.4933 -1.7663 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3415 3.4546 -0.6224 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5074 4.1984 -1.6882 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3402 5.6394 -1.7297 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9878 6.3803 -0.6349 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8440 7.7525 -0.7384 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0512 8.4019 -1.9408 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4058 7.6797 -3.0548 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5393 6.3217 -2.9149 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9059 9.7819 -2.0422 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6860 -3.3001 0.3042 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1240 0.1537 1.8316 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3937 2.1695 0.2992 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4865 -0.5250 -1.9721 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5451 2.4289 -3.4445 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4534 0.9795 -3.7640 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2006 0.8670 -4.0438 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0859 -0.1270 -1.8775 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6465 1.5298 -2.1607 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0240 0.2524 0.2524 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8126 -0.7405 -0.0104 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6996 1.9639 0.9087 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7933 1.7284 1.4812 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2178 0.5630 -0.8029 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2266 3.1920 -0.0810 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4349 3.2111 -0.5468 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7156 2.5841 -1.6676 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2742 -0.3026 2.0399 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3238 -1.3544 0.0607 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0347 -0.9412 1.8133 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9480 -0.4661 3.6243 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2689 -1.9911 2.5975 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3038 -0.9432 1.7987 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1323 -2.3894 -0.7809 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6232 -2.6989 2.2218 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0520 -5.0645 2.3038 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8116 -4.7225 2.6595 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3084 -7.1767 2.0932 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7961 -6.6523 0.4687 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6111 -6.9149 2.7089 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9628 -6.8237 1.9028 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6021 -5.6616 -1.9459 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2682 -5.7397 -1.1893 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9901 -6.8028 -1.3190 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2849 -0.6908 2.2196 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6389 -0.1901 1.8667 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6125 1.2105 1.4875 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1632 -0.4379 -0.7421 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8501 -0.4574 -0.7402 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0619 3.9118 0.3020 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7931 3.6770 -2.6050 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8154 5.9206 0.3245 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5644 8.3017 0.1500 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5781 8.1458 -4.0167 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8232 5.7611 -3.8152 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7583 10.3261 -1.1871 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4685 -3.6417 1.1889 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6535 0.8345 2.3625 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9195 2.4059 1.1243 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6670 -1.0942 -1.1748 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 14 17 1 0 13 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 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 28 31 1 0 21 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 45 48 1 0 20 49 1 0 5 50 1 0 4 51 1 0 3 52 1 0 7 2 1 0 15 9 1 0 36 19 1 0 47 42 1 0 30 25 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 6 3 57 1 6 4 58 1 1 5 59 1 6 6 60 1 1 9 61 1 1 10 62 1 6 11 63 1 0 11 64 1 0 11 65 1 0 13 66 1 1 14 67 1 6 15 68 1 1 16 69 1 0 17 70 1 0 19 71 1 1 20 72 1 6 21 73 1 1 23 74 1 0 23 75 1 0 24 76 1 0 24 77 1 0 26 78 1 0 27 79 1 0 29 80 1 0 30 81 1 0 31 82 1 0 33 83 1 1 34 84 1 0 34 85 1 0 35 86 1 0 36 87 1 6 40 88 1 0 41 89 1 0 43 90 1 0 44 91 1 0 46 92 1 0 47 93 1 0 48 94 1 0 49 95 1 0 50 96 1 0 51 97 1 0 52 98 1 0 M END

Standard InCHIKey	FNUMFJHHCJMAHD-CJEBOOSQSA-N
Standard InCHI	InChI=1S/C35H46O17/c1-16-24(40)25(41)27(43)34(47-16)51-30-17(2)48-35(28(44)26(30)42)52-32-29(45)33(46-14-13-19-5-10-21(38)11-6-19)49-22(15-36)31(32)50-23(39)12-7-18-3-8-20(37)9-4-18/h3-12,16-17,22,24-38,40-45H,13-15H2,1-2H3/b12-7+/t16-,17-,22+,24-,25+,26-,27+,28+,29+,30-,31+,32+,33+,34-,35-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1[C@H](C)O[C@H]([C@@H]([C@@H]1O)O)O[C@@H]1[C@H]([C@H](OCCc2ccc(cc2)O)O[C@H](CO)[C@H]1OC(=O)/C=C/c1ccc(cc1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	738.27	Volume:	699.476 ? Van der Waals volume.
Dense:	1.055	LogP:	0.682 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.281 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.294 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	32.0
TPSA:	263.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.088	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.189	Fsp³:	0.571
MCE-18:	124.091 ? 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:	0.71	Fluc inhibitor:	0.692 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.166 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.365 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.361	Promiscuous compounds:	0.319

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.666	MDCK Permeability:	-5.106
Pgp-inhibitor:	0.0	Pgp-substrate:	0.929
PAMPA:	1.0 ? 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):	0.593
20% Bioavailability (F20%):	0.885	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.008
Plasma Protein Binding (PPB):	72.632%	Volume Distribution (VD):	-0.289
Fu:	25.04% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.032

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.542
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.155 ? 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):

1.327

Half-life (T1/2):

4.164

ADMET: Toxicity

hERG Blockers:	0.042	hERG Blockers (10um):	0.175
Human Hepatotoxicity (H-HT):	0.427	Drug-induced Liver Injury (DILI):	0.752
AMES Toxicity:	0.957	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.013	Skin Sensitization:	1.0
Carcinogencity:	0.02	Eye Corrosion:	0.0
Eye Irritation:	0.01	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.995
Hematotoxicity:	0.238	Drug-induced Nephrotoxicity:	0.827
Genotoxicity:	0.294	RPMI-8226 Immunitoxicity:	0.168
A549 Cytotoxicity:	0.816	Hek293 Cytotoxicity:	0.932
BCF:	0.554 ? 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:	3.291 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.94 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.059 ? 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
NPO2726	Ligustrum robustum	Species	Oleaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828473]
NPO2726	Ligustrum robustum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2726	Ligustrum robustum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

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
IC50	1

Activity Type	# Activity
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.	IC50	=	80400.0	nM	PMID[12828473]

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 NPC263829 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	12460
0.1-0.2	32148
0.2-0.3	4619
0.3-0.4	507
0.4-0.5	67
0.5-0.6	25
0.6-0.7	20
0.7-0.8	1
0.8-0.85	0
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.925	High Similarity	NPC112
0.92	High Similarity	NPC46137
0.8537	High Similarity	NPC269141
0.7805	Intermediate Similarity	NPC472350
0.7805	Intermediate Similarity	NPC197316
0.7805	Intermediate Similarity	NPC89105
0.7381	Intermediate Similarity	NPC483705
0.7273	Intermediate Similarity	NPC34587
0.7033	Intermediate Similarity	NPC100998
0.7	Intermediate Similarity	NPC252292
0.6923	Remote Similarity	NPC296954
0.6854	Remote Similarity	NPC106677
0.6848	Remote Similarity	NPC34927
0.6506	Remote Similarity	NPC55608
0.6452	Remote Similarity	NPC298257
0.6452	Remote Similarity	NPC175214
0.6444	Remote Similarity	NPC76406
0.6374	Remote Similarity	NPC611289
0.6292	Remote Similarity	NPC483706
0.6277	Remote Similarity	NPC205864
0.6277	Remote Similarity	NPC247032
0.625	Remote Similarity	NPC235294
0.6154	Remote Similarity	NPC134405
0.6122	Remote Similarity	NPC476382
0.6082	Remote Similarity	NPC96795
0.6082	Remote Similarity	NPC264632
0.6061	Remote Similarity	NPC106818
0.6042	Remote Similarity	NPC119537
0.602	Remote Similarity	NPC300894
0.602	Remote Similarity	NPC23845
0.5825	Remote Similarity	NPC87403
0.5784	Remote Similarity	NPC476380
0.5784	Remote Similarity	NPC476381
0.5769	Remote Similarity	NPC306890
0.5747	Remote Similarity	NPC473285
0.5728	Remote Similarity	NPC470933
0.5728	Remote Similarity	NPC471062
0.5714	Remote Similarity	NPC81515
0.57	Remote Similarity	NPC259347
0.5673	Remote Similarity	NPC470934
0.5638	Remote Similarity	NPC68092
0.56	Remote Similarity	NPC610636
0.5581	Remote Similarity	NPC886
0.5566	Remote Similarity	NPC94871
0.5529	Remote Similarity	NPC288416
0.5421	Remote Similarity	NPC473427
0.5402	Remote Similarity	NPC471157
0.5288	Remote Similarity	NPC476384
0.5263	Remote Similarity	NPC64141
0.5234	Remote Similarity	NPC64195
0.5204	Remote Similarity	NPC257847
0.5189	Remote Similarity	NPC476378
0.5111	Remote Similarity	NPC34293
0.5094	Remote Similarity	NPC196063
0.5094	Remote Similarity	NPC604195

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC263829 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4947
0.1-0.2	4112
0.2-0.3	90
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
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
0.7805	Intermediate Similarity	NPD7266	Phase 2

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