NPASS Compound

Natural Product: NPC35119

Natural Product ID	NPC35119
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VRYWDBDPXMHHGE-HRPPYHBASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101474344
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 93 98 0 0 0 0 0 0 0 0999 V2000 8.1471 1.7145 -3.3601 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8269 1.4452 -1.9259 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0998 1.3425 -1.0756 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6328 0.8794 0.2944 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5364 1.7350 0.8390 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4738 2.0807 -0.1870 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0919 2.4963 -1.3676 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6498 1.0154 -0.4958 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2773 0.9331 -0.3299 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5207 1.9725 0.2072 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1413 1.8642 0.3634 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5042 0.7039 -0.0207 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2119 -0.3474 -0.5559 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5832 -0.1999 -0.6946 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5990 -1.4374 -0.9153 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2838 -1.6426 -0.8074 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1934 -2.9508 -1.2840 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5068 -3.2010 -1.5086 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8900 -4.4861 -1.9252 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9874 -5.4994 -2.1151 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3374 -5.1927 -1.8741 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7192 -3.9631 -1.4732 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3398 -6.7732 -2.5248 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4987 -0.6560 -0.2817 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1440 0.5275 0.1086 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5041 1.4827 0.5964 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8716 -0.7640 -0.1041 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3376 -1.1482 1.1503 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4835 -0.2839 1.6807 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4664 -0.4853 3.1771 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5892 -1.9602 3.4859 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8474 -2.8587 2.5640 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5473 -4.2249 2.5784 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8399 -4.1146 2.0725 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8226 -2.4533 1.2339 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9462 -2.3146 3.6220 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4981 0.1412 3.8460 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4130 1.0230 1.2848 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4223 1.4441 0.4669 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2413 2.6020 0.9726 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5242 2.5801 0.1273 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2491 2.4599 -1.3240 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9802 1.8014 -1.7128 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4721 2.4893 -2.9815 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4489 2.4753 -3.9721 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9581 1.8598 -0.7909 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3023 1.7059 -1.8948 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3522 3.6271 0.4502 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5749 2.5539 2.2958 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3985 2.8901 0.8930 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0439 2.9237 1.3967 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6932 0.8383 1.1722 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9955 0.4251 -1.5856 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6600 2.6278 -3.7630 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2491 1.8128 -3.5566 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8231 0.8485 -3.9928 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2905 0.4666 -1.8271 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5507 2.3504 -0.9850 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2408 -0.1676 0.1932 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0543 1.1810 1.6884 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9472 2.9647 0.2194 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9707 2.8836 0.5162 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1404 -1.0289 -1.1161 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2906 -2.4617 -1.4097 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9359 -4.6744 -2.0997 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0507 -5.9931 -2.0246 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7743 -3.7824 -1.2996 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7719 -7.3916 -1.8653 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5193 -1.0873 1.9243 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4039 -0.7576 1.2504 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4579 -0.1530 3.5363 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1533 -2.0887 4.5202 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8096 -3.0492 2.9114 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5962 -4.6314 3.5966 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0054 -4.9144 1.8677 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0244 -4.7073 1.3146 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5335 -1.5334 3.4513 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0994 0.7413 4.5256 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1338 0.5783 0.3238 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7379 3.5508 0.6736 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0527 1.6396 0.4541 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3590 3.4775 -1.7839 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1009 0.7235 -1.9913 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3193 3.5607 -2.6999 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5105 2.0821 -3.3200 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0108 3.3036 -3.9655 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4423 0.9456 -1.2441 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2445 4.4265 -0.1250 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9566 3.1339 2.8083 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7542 3.8028 1.1069 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8320 3.0098 2.3563 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3883 0.4886 2.0459 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9404 0.7462 -1.5385 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 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 20 23 1 0 16 24 2 0 24 25 1 0 25 26 2 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 29 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 43 46 1 0 42 47 1 0 41 48 1 0 40 49 1 0 11 50 1 0 5 51 1 0 4 52 1 0 3 53 1 0 7 2 1 0 14 9 1 0 22 17 1 0 35 28 1 0 46 39 1 0 25 12 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 6 3 58 1 1 4 59 1 6 5 60 1 1 6 61 1 1 10 62 1 0 14 63 1 0 18 64 1 0 19 65 1 0 21 66 1 0 22 67 1 0 23 68 1 0 28 69 1 1 29 70 1 6 30 71 1 1 31 72 1 1 32 73 1 1 33 74 1 0 33 75 1 0 34 76 1 0 36 77 1 0 37 78 1 0 39 79 1 6 40 80 1 1 41 81 1 1 42 82 1 6 43 83 1 6 44 84 1 0 44 85 1 0 45 86 1 0 47 87 1 0 48 88 1 0 49 89 1 0 50 90 1 0 51 91 1 0 52 92 1 0 53 93 1 0 M END

Standard InCHIKey	VRYWDBDPXMHHGE-HRPPYHBASA-N
Standard InCHI	InChI=1S/C33H40O20/c1-10-19(38)23(42)26(45)31(47-10)48-13-6-14(37)18-15(7-13)49-28(11-2-4-12(36)5-3-11)29(22(18)41)52-33-30(25(44)21(40)17(9-35)51-33)53-32-27(46)24(43)20(39)16(8-34)50-32/h2-7,10,16-17,19-21,23-27,30-40,42-46H,8-9H2,1H3/t10-,16+,17+,19-,20+,21-,23+,24-,25-,26+,27+,30+,31-,32-,33-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1cc(c2c(c1)oc(c1ccc(cc1)O)c(c2=O)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	756.21	Volume:	682.698 ? Van der Waals volume.
Dense:	1.108	LogP:	0.429 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.132 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.255 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	36.0
TPSA:	328.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	12.0	Rings:	6.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.099	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.3	Fsp³:	0.545
MCE-18:	150.706 ? 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:	0.621	Fluc inhibitor:	0.271 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.673 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.588 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.345	Promiscuous compounds:	0.578

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.931	MDCK Permeability:	-4.852
Pgp-inhibitor:	0.0	Pgp-substrate:	0.827
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):	0.999
20% Bioavailability (F20%):	0.839	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.086
Plasma Protein Binding (PPB):	80.605%	Volume Distribution (VD):	-0.064
Fu:	18.553% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.019
BSEP inhibitor:	0.0

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:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.875
HLM stability:	0.0 ? 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):

0.984

Half-life (T1/2):

5.477

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.017
Human Hepatotoxicity (H-HT):	0.743	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.989	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.022	Eye Corrosion:	0.0
Eye Irritation:	0.032	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.997
Hematotoxicity:	0.403	Drug-induced Nephrotoxicity:	0.91
Genotoxicity:	0.88	RPMI-8226 Immunitoxicity:	0.306
A549 Cytotoxicity:	0.98	Hek293 Cytotoxicity:	0.731
BCF:	0.353 ? 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:	2.795 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.484 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.487 ? 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
NPO28620	Elaeagnus umbellata	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32031808]
NPO28620	Elaeagnus umbellata	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28620	Elaeagnus umbellata	Species	Elaeagnaceae	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	13

Activity Type	# Activity
Cell line	13

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
NPT4909	Cell line	Fibroblasts	n.a.	Activity	=	14.2	%	PMID[32031808]
NPT4909	Cell line	Fibroblasts	n.a.	Activity	=	13.0	%	PMID[32031808]
NPT4909	Cell line	Fibroblasts	n.a.	Activity	=	69.8	%	PMID[32031808]
NPT4909	Cell line	Fibroblasts	n.a.	Activity	=	10.5	%	PMID[32031808]
NPT4909	Cell line	Fibroblasts	n.a.	Activity	=	4.8	%	PMID[32031808]
NPT4909	Cell line	Fibroblasts	n.a.	Activity	=	81.5	%	PMID[32031808]
NPT4909	Cell line	Fibroblasts	n.a.	Activity	=	10.0	%	PMID[32031808]
NPT4909	Cell line	Fibroblasts	n.a.	Activity	=	90.0	%	PMID[32031808]
NPT4909	Cell line	Fibroblasts	n.a.	Activity	=	6.7	%	PMID[32031808]
NPT4909	Cell line	Fibroblasts	n.a.	Activity	=	93.3	%	PMID[32031808]
NPT4909	Cell line	Fibroblasts	n.a.	Activity	=	124.2	%	PMID[32031808]
NPT4909	Cell line	Fibroblasts	n.a.	Activity	=	68.8	%	PMID[32031808]
NPT4909	Cell line	Fibroblasts	n.a.	Activity	=	125.6	%	PMID[32031808]

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 NPC35119 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	24583
0.1-0.2	21085
0.2-0.3	3224
0.3-0.4	460
0.4-0.5	258
0.5-0.6	121
0.6-0.7	53
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9753	High Similarity	NPC32641
0.9753	High Similarity	NPC256188
0.881	High Similarity	NPC240306
0.837	Intermediate Similarity	NPC25523
0.8293	Intermediate Similarity	NPC116458
0.8293	Intermediate Similarity	NPC246943
0.8161	Intermediate Similarity	NPC64425
0.7778	Intermediate Similarity	NPC249281
0.7683	Intermediate Similarity	NPC297987
0.7614	Intermediate Similarity	NPC163242
0.7614	Intermediate Similarity	NPC272068
0.7604	Intermediate Similarity	NPC480441
0.7553	Intermediate Similarity	NPC14187
0.7442	Intermediate Similarity	NPC605784
0.7381	Intermediate Similarity	NPC46420
0.7356	Intermediate Similarity	NPC170052
0.7356	Intermediate Similarity	NPC135846
0.7333	Intermediate Similarity	NPC65003
0.7312	Intermediate Similarity	NPC142142
0.7191	Intermediate Similarity	NPC473682
0.7159	Intermediate Similarity	NPC276377
0.7071	Intermediate Similarity	NPC164704
0.7065	Intermediate Similarity	NPC470444
0.7065	Intermediate Similarity	NPC186816
0.7	Intermediate Similarity	NPC251417
0.6957	Remote Similarity	NPC155877
0.6957	Remote Similarity	NPC150164
0.6941	Remote Similarity	NPC289667
0.6882	Remote Similarity	NPC115674
0.686	Remote Similarity	NPC136042
0.6778	Remote Similarity	NPC476215
0.6735	Remote Similarity	NPC602448
0.6733	Remote Similarity	NPC470715
0.6703	Remote Similarity	NPC254855
0.6703	Remote Similarity	NPC94610
0.6667	Remote Similarity	NPC470717
0.663	Remote Similarity	NPC8856
0.6591	Remote Similarity	NPC84362
0.6591	Remote Similarity	NPC271692
0.6531	Remote Similarity	NPC473071
0.6531	Remote Similarity	NPC220173
0.6495	Remote Similarity	NPC72016
0.6449	Remote Similarity	NPC470720
0.6444	Remote Similarity	NPC611303
0.6421	Remote Similarity	NPC304741
0.6389	Remote Similarity	NPC209550
0.6364	Remote Similarity	NPC195257
0.6364	Remote Similarity	NPC76831
0.6316	Remote Similarity	NPC470405
0.625	Remote Similarity	NPC111929
0.625	Remote Similarity	NPC320283
0.625	Remote Similarity	NPC331652
0.625	Remote Similarity	NPC41121
0.6224	Remote Similarity	NPC12013
0.6224	Remote Similarity	NPC11432
0.6224	Remote Similarity	NPC477613
0.6182	Remote Similarity	NPC175429
0.618	Remote Similarity	NPC39360
0.618	Remote Similarity	NPC77672
0.618	Remote Similarity	NPC108831
0.618	Remote Similarity	NPC133671
0.618	Remote Similarity	NPC135391
0.618	Remote Similarity	NPC29763
0.618	Remote Similarity	NPC78263
0.618	Remote Similarity	NPC210003
0.618	Remote Similarity	NPC250069
0.618	Remote Similarity	NPC182634
0.617	Remote Similarity	NPC95866
0.6168	Remote Similarity	NPC295625
0.6111	Remote Similarity	NPC158674
0.6111	Remote Similarity	NPC323593
0.6111	Remote Similarity	NPC203500
0.6091	Remote Similarity	NPC138990
0.6058	Remote Similarity	NPC473072
0.6044	Remote Similarity	NPC24043
0.6042	Remote Similarity	NPC139320
0.6022	Remote Similarity	NPC224530
0.6	Remote Similarity	NPC219043
0.598	Remote Similarity	NPC292929
0.5963	Remote Similarity	NPC298666
0.5909	Remote Similarity	NPC470719
0.5859	Remote Similarity	NPC255157
0.5859	Remote Similarity	NPC259896
0.5833	Remote Similarity	NPC255799
0.5825	Remote Similarity	NPC221342
0.5825	Remote Similarity	NPC476470
0.5824	Remote Similarity	NPC19709
0.5824	Remote Similarity	NPC238376
0.5761	Remote Similarity	NPC64305
0.5761	Remote Similarity	NPC277205
0.5761	Remote Similarity	NPC37919
0.5761	Remote Similarity	NPC189142
0.5761	Remote Similarity	NPC77660
0.5752	Remote Similarity	NPC192539
0.5728	Remote Similarity	NPC475382
0.5714	Remote Similarity	NPC480466
0.5701	Remote Similarity	NPC48984
0.57	Remote Similarity	NPC122809
0.5699	Remote Similarity	NPC488080
0.5699	Remote Similarity	NPC169977
0.5688	Remote Similarity	NPC470716
0.5686	Remote Similarity	NPC122467
0.5686	Remote Similarity	NPC606657
0.5678	Remote Similarity	NPC223860
0.566	Remote Similarity	NPC203145
0.5657	Remote Similarity	NPC173582
0.5657	Remote Similarity	NPC44931
0.5657	Remote Similarity	NPC265885
0.5657	Remote Similarity	NPC181465
0.5657	Remote Similarity	NPC215710
0.5657	Remote Similarity	NPC473438
0.5657	Remote Similarity	NPC253788
0.5652	Remote Similarity	NPC127546
0.5652	Remote Similarity	NPC57625
0.5652	Remote Similarity	NPC173637
0.5652	Remote Similarity	NPC317489
0.5652	Remote Similarity	NPC223424
0.5652	Remote Similarity	NPC600591
0.5648	Remote Similarity	NPC470712
0.5638	Remote Similarity	NPC472459
0.5619	Remote Similarity	NPC253685
0.5607	Remote Similarity	NPC189564
0.5596	Remote Similarity	NPC311850
0.5591	Remote Similarity	NPC145038
0.5591	Remote Similarity	NPC8573
0.5591	Remote Similarity	NPC56077
0.5591	Remote Similarity	NPC281131
0.5591	Remote Similarity	NPC253662
0.5591	Remote Similarity	NPC179950
0.5591	Remote Similarity	NPC88789
0.5591	Remote Similarity	NPC491374
0.5536	Remote Similarity	NPC198199
0.5536	Remote Similarity	NPC480445
0.5532	Remote Similarity	NPC27640
0.5514	Remote Similarity	NPC121703
0.5514	Remote Similarity	NPC25724
0.55	Remote Similarity	NPC471748
0.5495	Remote Similarity	NPC288084
0.5484	Remote Similarity	NPC261866
0.5484	Remote Similarity	NPC348541
0.5474	Remote Similarity	NPC216496
0.5472	Remote Similarity	NPC135358
0.5455	Remote Similarity	NPC239549
0.5455	Remote Similarity	NPC277532
0.5446	Remote Similarity	NPC488739
0.5446	Remote Similarity	NPC605592
0.5437	Remote Similarity	NPC483414
0.5426	Remote Similarity	NPC197896
0.5426	Remote Similarity	NPC95090
0.5426	Remote Similarity	NPC313163
0.5426	Remote Similarity	NPC27408
0.5417	Remote Similarity	NPC307938
0.5417	Remote Similarity	NPC285197
0.5417	Remote Similarity	NPC488071
0.54	Remote Similarity	NPC29958
0.5385	Remote Similarity	NPC482026
0.5385	Remote Similarity	NPC25946
0.5376	Remote Similarity	NPC473043
0.537	Remote Similarity	NPC89052
0.5361	Remote Similarity	NPC22832
0.5361	Remote Similarity	NPC601144
0.5347	Remote Similarity	NPC67105
0.534	Remote Similarity	NPC61904
0.5333	Remote Similarity	NPC5319
0.5312	Remote Similarity	NPC59534
0.5312	Remote Similarity	NPC599850
0.531	Remote Similarity	NPC68592
0.531	Remote Similarity	NPC488734
0.531	Remote Similarity	NPC488735
0.531	Remote Similarity	NPC488732
0.531	Remote Similarity	NPC488738
0.5306	Remote Similarity	NPC223747
0.5306	Remote Similarity	NPC136761
0.5306	Remote Similarity	NPC311830
0.53	Remote Similarity	NPC480463
0.5294	Remote Similarity	NPC65563
0.5294	Remote Similarity	NPC210073
0.5294	Remote Similarity	NPC470949
0.5294	Remote Similarity	NPC156869
0.5268	Remote Similarity	NPC470718
0.5263	Remote Similarity	NPC470713
0.5259	Remote Similarity	NPC120952
0.5258	Remote Similarity	NPC168584
0.5258	Remote Similarity	NPC60735
0.5258	Remote Similarity	NPC219904
0.5258	Remote Similarity	NPC26230
0.5253	Remote Similarity	NPC203050
0.5253	Remote Similarity	NPC225434
0.5253	Remote Similarity	NPC66087
0.5243	Remote Similarity	NPC473571
0.5243	Remote Similarity	NPC110941
0.5225	Remote Similarity	NPC303694
0.5213	Remote Similarity	NPC135599
0.5213	Remote Similarity	NPC73855
0.5213	Remote Similarity	NPC113968
0.5213	Remote Similarity	NPC328940
0.5213	Remote Similarity	NPC277174
0.5213	Remote Similarity	NPC606877
0.5208	Remote Similarity	NPC305811

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC35119 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6128
0.1-0.2	2951
0.2-0.3	62
0.3-0.4	3
0.4-0.5	2
0.5-0.6	4
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
0.5882	Remote Similarity	NPD7251	Phase 2
0.5514	Remote Similarity	NPD7808	Phase 3
0.5333	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5146	Remote Similarity	NPD6797	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