NPASS Compound

Natural Product: NPC477332

Natural Product ID	NPC477332
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Murucin 5
IUPAC Name	[(2S,3R,4R,5R,6S)-4-hydroxy-5-[(2S,3R,4R,5R,6S)-4-hydroxy-5-(3-hydroxy-2-methylbutanoyl)oxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methyl-2-[[(1R,5S,6R,7R,8R,22R,24R,25S,26S)-7,25,26-trihydroxy-5,24-dimethyl-10-oxo-20-pentyl-2,4,9,21,23-pentaoxatricyclo[20.4.0.03,8]hexacosan-6-yl]oxy]oxan-3-yl] dodecanoate
Synonyms	Murucin 5
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44559240
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 2D 199204 0 0 0 0 0 0 0 0999 V2000 -15.9040 0.4257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.4945 -0.0873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.0849 -0.6004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6754 -1.1134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2658 -1.6264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8563 -2.1395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4468 -2.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0372 -3.1655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6277 -3.6786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2181 -4.1916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8086 -4.7046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 -5.2176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1386 -6.6949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -4.2535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -4.7665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3086 -5.7307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7181 -5.2176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 -3.7404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 -2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 -3.2893 0.0000 C 0 0 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 6.5167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 5.5525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 4.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 4.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 5.5525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 6.8515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 6.8515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4895 8.3287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 6.5167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 3.7404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0292 8.1208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9999 9.2118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9705 10.3029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0588 11.3940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0882 12.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3882 -4.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 -6.6949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3882 -7.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6382 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0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 48 50 1 0 47 51 1 0 46 52 1 0 41 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 23 58 1 0 18 59 1 0 17 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 65 67 1 0 64 68 1 0 68 69 1 0 69 70 2 0 69 71 1 0 71 72 1 0 71 73 1 0 73 74 1 0 73 75 1 0 63 76 1 0 62 77 1 0 77 78 1 0 78 79 1 0 79 80 1 0 80 81 1 0 81 82 1 0 82 83 1 0 82 84 1 0 84 85 1 0 81 86 1 0 80 87 1 0 79 88 1 0 16 89 1 0 20 15 1 0 27 22 1 0 45 25 1 0 49 43 1 0 66 61 1 0 83 78 1 0 1 90 1 0 1 91 1 0 1 92 1 0 2 93 1 0 2 94 1 0 3 95 1 0 3 96 1 0 4 97 1 0 4 98 1 0 5 99 1 0 5100 1 0 6101 1 0 6102 1 0 7103 1 0 7104 1 0 8105 1 0 8106 1 0 9107 1 0 9108 1 0 10109 1 0 10110 1 0 11111 1 0 11112 1 0 15113 1 6 16114 1 6 17115 1 1 18116 1 6 20117 1 1 22118 1 1 23119 1 6 25120 1 0 26121 1 6 27122 1 6 28123 1 0 32124 1 0 32125 1 0 33126 1 0 33127 1 0 34128 1 0 34129 1 0 35130 1 0 35131 1 0 36132 1 0 36133 1 0 37134 1 0 37135 1 0 38136 1 0 38137 1 0 39138 1 0 39139 1 0 40140 1 0 40141 1 0 41142 1 0 43143 1 1 44144 1 6 46145 1 1 47146 1 6 48147 1 1 50148 1 0 50149 1 0 50150 1 0 51151 1 0 52152 1 0 53153 1 0 53154 1 0 54155 1 0 54156 1 0 55157 1 0 55158 1 0 56159 1 0 56160 1 0 57161 1 0 57162 1 0 57163 1 0 58164 1 0 58165 1 0 58166 1 0 59167 1 0 59168 1 0 59169 1 0 61170 1 1 62171 1 6 63172 1 6 64173 1 1 65174 1 6 67175 1 0 67176 1 0 67177 1 0 71178 1 0 72179 1 0 72180 1 0 72181 1 0 73182 1 0 74183 1 0 74184 1 0 74185 1 0 75186 1 0 76187 1 0 78188 1 1 79189 1 6 80190 1 1 81191 1 6 82192 1 1 84193 1 0 84194 1 0 85195 1 0 86196 1 0 87197 1 0 88198 1 0 89199 1 0 M END

Standard InCHIKey	SENFYNXWLSWSPD-QCJRRDSLSA-N
Standard InCHI	InChI=1S/C63H110O26/c1-9-11-13-14-15-16-19-22-26-30-41(66)83-55-49(74)53(87-63-57(88-59-47(72)45(70)44(69)40(32-64)82-59)48(73)51(36(6)78-63)85-58(76)33(3)34(4)65)37(7)79-61(55)86-52-38(8)80-62-56(50(52)75)84-42(67)31-27-23-20-17-18-21-25-29-39(28-24-12-10-2)81-60-54(89-62)46(71)43(68)35(5)77-60/h33-40,43-57,59-65,68-75H,9-32H2,1-8H3/t33?,34?,35-,36+,37+,38+,39?,40-,43-,44-,45+,46+,47-,48-,49-,50-,51+,52+,53+,54-,55-,56-,57-,59+,60+,61+,62?,63+/m1/s1
SMILES	CCCCCCCCCCCC(=O)O[C@@H]1[C@@H]([C@H]([C@@H](O[C@H]1O[C@H]2[C@@H](OC3[C@@H]([C@@H]2O)OC(=O)CCCCCCCCCC(O[C@H]4[C@H](O3)[C@H]([C@@H]([C@H](O4)C)O)O)CCCCC)C)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC(=O)C(C)C(C)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1282.73	Volume:	1267.501 ? Van der Waals volume.
Dense:	1.012	LogP:	4.8 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.435 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.102 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	27.0	Rigid Bonds:	49.0
TPSA:	373.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	26.0
H-Bond Donor:	10.0	Rings:	6.0
Heavy Atoms:	26.0

MedChem Properties

QED Drug-Likeness Score:	0.036	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.503	Fsp³:	0.952
MCE-18:	125.886 ? 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:	0.986	Fluc inhibitor:	0.071 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.006 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.473	Promiscuous compounds:	0.047

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.561	MDCK Permeability:	-4.972
Pgp-inhibitor:	0.0	Pgp-substrate:	0.774
PAMPA:	0.877 ? 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):	0.018
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.846
50% Bioavailability (F50%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.988
Plasma Protein Binding (PPB):	92.781%	Volume Distribution (VD):	-0.209
Fu:	5.475% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.432

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:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.973
HLM stability:	0.718 ? 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):

0.507

Half-life (T1/2):

3.799

ADMET: Toxicity

hERG Blockers:	0.033	hERG Blockers (10um):	0.115
Human Hepatotoxicity (H-HT):	0.384	Drug-induced Liver Injury (DILI):	0.953
AMES Toxicity:	0.176	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.0	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.295	Drug-induced Nephrotoxicity:	0.787
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.401
A549 Cytotoxicity:	0.988	Hek293 Cytotoxicity:	0.28
BCF:	0.359 ? 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:	4.323 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.164 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.464 ? 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
NPO2520	Ipomoea murucoides	Species	Convolvulaceae	Eukaryota	Roots	Ixpantepec, in the state of Oaxaca, Mexico	1996-DEC	PMID[16124750]
NPO2520	Ipomoea murucoides	Species	Convolvulaceae	Eukaryota	flowers	n.a.	n.a.	PMID[16643033]
NPO2520	Ipomoea murucoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18500841]
NPO2520	Ipomoea murucoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	3

Activity Type	# Activity
Cell line	2
Others	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
NPT148	Cell line	HCT-15	Homo sapiens	ED50	>	20	ug/ml	PMID[16124750]
NPT382	Cell line	OVCAR-5	Homo sapiens	ED50	>	20	ug/ml	PMID[16124750]
NPT2	Others	Unspecified	n.a.	ED50	>	20	ug/ml	PMID[16124750]

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 NPC477332 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	22690
0.1-0.2	22904
0.2-0.3	3635
0.3-0.4	477
0.4-0.5	38
0.5-0.6	57
0.6-0.7	40
0.7-0.8	0
0.8-0.85	1
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8919	High Similarity	NPC477331
0.875	High Similarity	NPC477328
0.875	High Similarity	NPC477330
0.8714	High Similarity	NPC478729
0.863	High Similarity	NPC477329
0.8333	Intermediate Similarity	NPC478722
0.7765	Intermediate Similarity	NPC478728
0.7674	Intermediate Similarity	NPC478727
0.7654	Intermediate Similarity	NPC478725
0.7561	Intermediate Similarity	NPC478723
0.7561	Intermediate Similarity	NPC478724
0.7412	Intermediate Similarity	NPC224953
0.7381	Intermediate Similarity	NPC478726
0.7317	Intermediate Similarity	NPC109887
0.7024	Intermediate Similarity	NPC60849
0.6867	Remote Similarity	NPC89843
0.6818	Remote Similarity	NPC184915
0.6667	Remote Similarity	NPC44782
0.6667	Remote Similarity	NPC119583
0.6552	Remote Similarity	NPC297768
0.6531	Remote Similarity	NPC290276
0.6517	Remote Similarity	NPC238056
0.6517	Remote Similarity	NPC115013
0.6404	Remote Similarity	NPC483170
0.6395	Remote Similarity	NPC600446
0.6395	Remote Similarity	NPC605013
0.6374	Remote Similarity	NPC472200
0.6333	Remote Similarity	NPC169345
0.6304	Remote Similarity	NPC269318
0.6264	Remote Similarity	NPC183888
0.6264	Remote Similarity	NPC126685
0.6235	Remote Similarity	NPC22742
0.6235	Remote Similarity	NPC477349
0.6235	Remote Similarity	NPC477346
0.6224	Remote Similarity	NPC28069
0.622	Remote Similarity	NPC477350
0.6214	Remote Similarity	NPC600940
0.6207	Remote Similarity	NPC479059
0.6207	Remote Similarity	NPC477326
0.618	Remote Similarity	NPC472205
0.6163	Remote Similarity	NPC604005
0.6163	Remote Similarity	NPC605014
0.6145	Remote Similarity	NPC475425
0.6129	Remote Similarity	NPC477347
0.6111	Remote Similarity	NPC472204
0.6111	Remote Similarity	NPC206823
0.6092	Remote Similarity	NPC478734
0.6067	Remote Similarity	NPC146992
0.6067	Remote Similarity	NPC85759
0.6067	Remote Similarity	NPC479061
0.6061	Remote Similarity	NPC77651
0.6042	Remote Similarity	NPC475241
0.6023	Remote Similarity	NPC477344
0.6	Remote Similarity	NPC479058
0.6	Remote Similarity	NPC479060
0.5955	Remote Similarity	NPC478733
0.5934	Remote Similarity	NPC294748
0.5914	Remote Similarity	NPC479057
0.5851	Remote Similarity	NPC163409
0.5814	Remote Similarity	NPC281563
0.5804	Remote Similarity	NPC147032
0.5761	Remote Similarity	NPC478730
0.5761	Remote Similarity	NPC186992
0.5745	Remote Similarity	NPC259294
0.5714	Remote Similarity	NPC267592
0.5701	Remote Similarity	NPC471026
0.5699	Remote Similarity	NPC238264
0.5699	Remote Similarity	NPC477345
0.5682	Remote Similarity	NPC87153
0.5673	Remote Similarity	NPC610996
0.5652	Remote Similarity	NPC173328
0.5638	Remote Similarity	NPC478732
0.5638	Remote Similarity	NPC478731
0.5638	Remote Similarity	NPC477317
0.5638	Remote Similarity	NPC477318
0.5591	Remote Similarity	NPC143421
0.5591	Remote Similarity	NPC307400
0.5591	Remote Similarity	NPC27289
0.5581	Remote Similarity	NPC146380
0.5579	Remote Similarity	NPC475270
0.5579	Remote Similarity	NPC475327
0.5532	Remote Similarity	NPC476087
0.5532	Remote Similarity	NPC475667
0.5506	Remote Similarity	NPC113745
0.5506	Remote Similarity	NPC477320
0.5506	Remote Similarity	NPC477323
0.5506	Remote Similarity	NPC477325
0.5506	Remote Similarity	NPC609436
0.5484	Remote Similarity	NPC477319
0.5474	Remote Similarity	NPC290012
0.5463	Remote Similarity	NPC610997
0.5455	Remote Similarity	NPC477348
0.5429	Remote Similarity	NPC10883
0.5421	Remote Similarity	NPC600721
0.5421	Remote Similarity	NPC605872
0.5412	Remote Similarity	NPC606819
0.5361	Remote Similarity	NPC123204
0.5327	Remote Similarity	NPC471025
0.5315	Remote Similarity	NPC471024
0.5306	Remote Similarity	NPC476066
0.5283	Remote Similarity	NPC10121
0.5283	Remote Similarity	NPC198918
0.5204	Remote Similarity	NPC475525
0.5204	Remote Similarity	NPC475540
0.52	Remote Similarity	NPC473605
0.52	Remote Similarity	NPC475375
0.52	Remote Similarity	NPC241265
0.5161	Remote Similarity	NPC158302
0.5155	Remote Similarity	NPC162925
0.514	Remote Similarity	NPC611287
0.51	Remote Similarity	NPC475164
0.5067	Remote Similarity	NPC76881

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477332 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7289
0.1-0.2	1756
0.2-0.3	100
0.3-0.4	5
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