NPASS Compound

Natural Product: NPC244875

Natural Product ID	NPC244875
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Evolvoside E
IUPAC Name	2-[4-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxyphenyl]-3-hydroxy-5,7-dimethoxychromen-4-one
Synonyms	Evolvoside E
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2336774
PubChem CID	71524830
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides

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 -2.5922 -4.3351 0.8177 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5840 -3.2365 0.4964 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9788 -3.7513 0.8431 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7928 -2.5438 1.2668 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4487 -1.4058 0.3307 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9987 -1.0212 0.6047 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3071 -0.8042 -0.5839 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8062 0.4619 -0.7184 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8480 0.9033 0.3403 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4413 2.3364 -0.0399 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8692 2.9560 1.2005 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1528 1.9028 1.9735 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3174 0.7306 1.1338 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3684 1.1179 0.3124 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6576 0.6748 0.4460 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1420 -0.1882 1.3862 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4990 -0.5778 1.4285 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3904 -0.1101 0.5321 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9173 0.7708 -0.4350 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6010 1.1477 -0.4746 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8052 -0.4469 0.4999 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4474 -1.2645 1.3870 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8198 -1.5184 1.2579 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3915 -2.2762 2.0882 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5183 -0.9359 0.2269 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8719 -1.1629 0.0675 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5599 -0.5737 -0.9696 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8657 0.2567 -1.8564 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5216 0.4812 -1.6963 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8232 -0.1168 -0.6441 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5685 0.0681 -0.4617 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5991 0.8323 -2.8909 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9475 1.6759 -3.8111 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4957 -1.9945 0.9803 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8768 -2.2362 0.8321 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7733 -1.8681 2.4386 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7288 0.1279 0.4463 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8566 1.4746 3.1027 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0689 4.0596 0.9118 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5023 3.0425 -0.5806 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3656 -2.0843 1.2445 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2617 -0.3334 0.6267 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0333 0.1057 -0.4513 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4889 0.1545 -0.0500 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.2610 0.7947 -1.1513 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4617 1.3645 -2.2668 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1302 1.9158 -1.8836 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1703 3.4178 -1.7751 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9758 3.8410 -0.7231 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6281 1.4136 -0.6991 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3310 0.4697 -3.3445 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2107 1.7198 -0.6546 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9742 -1.1055 0.2937 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3701 -2.1775 2.5383 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6010 -4.3495 -0.2281 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6960 -5.0968 -0.0102 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5426 -3.9610 0.8516 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8527 -4.8662 1.7529 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5923 -3.0469 -0.5935 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8705 -4.4765 1.6886 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8692 -2.8061 1.2331 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5662 -1.7216 -0.7278 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0192 -0.1453 1.2570 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3162 0.5355 -1.7028 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6780 1.1699 -0.7611 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3128 1.0045 1.3390 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6841 2.2395 -0.8520 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7481 3.2986 1.8178 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7923 2.3684 2.3823 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6697 -0.0213 1.8594 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4940 -0.5985 2.1300 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7886 -1.2610 2.2012 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5844 1.1898 -1.1949 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2255 1.8371 -1.2295 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6138 -0.7752 -1.0594 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9660 1.1105 -2.3586 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7393 2.1685 -4.4132 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3157 1.0906 -4.5193 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2768 2.4134 -3.3145 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1410 -2.6575 -0.1610 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2847 -2.8941 1.6084 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4494 -1.2680 0.8976 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7338 -2.8716 2.5499 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0860 2.3282 3.5912 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8974 3.7764 0.9525 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8103 3.7795 -0.0083 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8838 -0.4673 -1.3715 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6005 0.7810 0.8750 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9051 -0.0190 -1.6017 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0628 2.2229 -2.6919 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3999 1.6558 -2.6846 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5786 3.8764 -2.7243 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1728 3.8559 -1.6447 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4666 4.2671 0.0105 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2537 0.1341 -3.5702 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8851 2.1068 0.2086 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1199 -1.2133 1.2624 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1138 -2.9533 3.0982 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4243 -3.8901 -0.4632 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 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 18 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 28 32 1 0 32 33 1 0 26 34 1 0 34 35 1 0 22 36 1 0 13 37 1 0 12 38 1 0 11 39 1 0 10 40 1 0 6 41 1 0 5 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 47 50 1 0 46 51 1 0 45 52 1 0 44 53 1 0 4 54 1 0 3 55 1 0 41 2 1 0 50 43 1 0 37 9 1 0 20 15 1 0 31 21 1 0 30 25 1 0 1 56 1 0 1 57 1 0 1 58 1 0 2 59 1 6 3 60 1 1 4 61 1 1 5 62 1 6 6 63 1 1 8 64 1 0 8 65 1 0 9 66 1 1 10 67 1 6 11 68 1 1 12 69 1 1 13 70 1 1 16 71 1 0 17 72 1 0 19 73 1 0 20 74 1 0 27 75 1 0 29 76 1 0 33 77 1 0 33 78 1 0 33 79 1 0 35 80 1 0 35 81 1 0 35 82 1 0 36 83 1 0 38 84 1 0 39 85 1 0 40 86 1 0 43 87 1 6 44 88 1 1 45 89 1 6 46 90 1 6 47 91 1 6 48 92 1 0 48 93 1 0 49 94 1 0 51 95 1 0 52 96 1 0 53 97 1 0 54 98 1 0 55 99 1 0 M END

Standard InCHIKey	HRMACLKTDXQZNB-VFCYDLCPSA-N
Standard InCHI	InChI=1S/C35H44O20/c1-12-21(37)27(43)32(55-34-30(46)25(41)22(38)18(10-36)53-34)35(50-12)49-11-19-23(39)26(42)29(45)33(54-19)51-14-6-4-13(5-7-14)31-28(44)24(40)20-16(48-3)8-15(47-2)9-17(20)52-31/h4-9,12,18-19,21-23,25-27,29-30,32-39,41-46H,10-11H2,1-3H3/t12-,18+,19+,21-,22+,23+,25-,26-,27+,29+,30+,32+,33+,34-,35+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](Oc3ccc(cc3)c3c(c(=O)c4c(cc(cc4o3)OC)OC)O)O2)O)O)O)O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17473466]
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23357036]
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24634069]
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	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
Activity	2

Activity Type	# Activity
Organism	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

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	252.6	ng/ml	PMID[10514320]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	413.7	mg/dl	PMID[26210507]

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 NPC244875 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	17715
0.1-0.2	26982
0.2-0.3	4132
0.3-0.4	735
0.4-0.5	248
0.5-0.6	37
0.6-0.7	0
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8172	Intermediate Similarity	NPC135358
0.75	Intermediate Similarity	NPC287889
0.59	Remote Similarity	NPC187379
0.5825	Remote Similarity	NPC475366
0.5686	Remote Similarity	NPC275454
0.5588	Remote Similarity	NPC295613
0.5588	Remote Similarity	NPC473657
0.5534	Remote Similarity	NPC67105
0.5487	Remote Similarity	NPC311850
0.5481	Remote Similarity	NPC102028
0.5446	Remote Similarity	NPC61791
0.5385	Remote Similarity	NPC227508
0.5377	Remote Similarity	NPC284277
0.5377	Remote Similarity	NPC475497
0.5347	Remote Similarity	NPC136761
0.5345	Remote Similarity	NPC68592
0.5333	Remote Similarity	NPC473512
0.5333	Remote Similarity	NPC22062
0.5333	Remote Similarity	NPC129827
0.5333	Remote Similarity	NPC473634
0.5333	Remote Similarity	NPC138811
0.5306	Remote Similarity	NPC609879
0.5283	Remote Similarity	NPC204693
0.5273	Remote Similarity	NPC470445
0.5248	Remote Similarity	NPC486578
0.5233	Remote Similarity	NPC276905
0.52	Remote Similarity	NPC182045
0.5182	Remote Similarity	NPC470447
0.5182	Remote Similarity	NPC475382
0.5169	Remote Similarity	NPC198199
0.513	Remote Similarity	NPC480441
0.51	Remote Similarity	NPC610763
0.5098	Remote Similarity	NPC284960
0.5094	Remote Similarity	NPC15358
0.5082	Remote Similarity	NPC262222
0.505	Remote Similarity	NPC117260
0.5047	Remote Similarity	NPC233994
0.5046	Remote Similarity	NPC211532
0.5041	Remote Similarity	NPC120952

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC244875 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4797
0.1-0.2	4256
0.2-0.3	87
0.3-0.4	4
0.4-0.5	4
0.5-0.6	1
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
0.5545	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