NPASS Compound

Natural Product: NPC505807

Natural Product ID	NPC505807
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{R},3~{S},4~{S},5~{R},6~{S})-6-[4-[7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-6-carboxy-3-[(2~{R},3~{S},4~{S},5~{S},6~{S})-6-carboxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-4,5-dihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-4-oxo-chromen-2-yl]-2-hydroxy-phenoxy]-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
IUPAC Name	(2~{R},3~{S},4~{S},5~{R},6~{S})-6-[4-[7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-6-carboxy-3-[(2~{R},3~{S},4~{S},5~{S},6~{S})-6-carboxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-4,5-dihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-4-oxo-chromen-2-yl]-2-hydroxy-phenoxy]-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0002934] Flavonoid O-glucuronides [CHEMONTID:0003534] Flavonoid-7-O-glucuronides

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 91 96 0 0 0 0 0 0 0 0999 V2000 10.2756 0.7902 0.8293 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0387 0.6373 0.7889 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3014 1.2490 -0.1956 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3769 -0.2032 1.8056 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0237 -0.3255 1.6635 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5750 -1.1854 0.6807 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3104 -0.4399 -0.4340 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9924 -0.4216 -0.8617 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3766 0.9705 -0.6783 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9904 0.8101 -0.6587 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1535 0.9358 0.4122 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5458 1.2288 1.7012 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6285 1.3381 2.7362 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0185 1.6320 4.0335 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2892 1.1539 2.4935 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6156 1.2631 3.5265 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2309 1.5270 4.6767 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9598 1.0626 3.2026 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3564 0.7720 1.9194 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7463 0.5593 1.5408 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7751 0.5819 2.4146 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1029 0.3899 1.9997 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3983 0.1721 0.6818 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6705 -0.0172 0.2364 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8686 -0.0587 0.9208 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.5479 -1.2315 0.5999 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8327 -1.2763 -0.7648 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.4166 -2.5491 -1.1973 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6572 -3.5172 -0.4403 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7205 -2.6719 -2.5585 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7385 -0.1321 -1.1768 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.9000 -0.0989 -0.3965 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9791 1.1632 -0.8754 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7960 1.1158 -1.6051 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7333 1.1629 0.6233 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.9649 1.0394 1.2543 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3500 0.1481 -0.2123 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6560 -0.0753 -1.5551 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0353 0.3376 0.1976 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4023 0.6924 1.0133 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1414 0.8606 1.2177 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8065 0.7562 0.1930 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7090 1.8135 -1.7073 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0429 1.3703 -2.8426 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2551 2.3786 -3.9126 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9234 3.4249 -3.7722 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6565 2.1180 -5.1525 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6628 0.0878 -3.2987 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9334 0.4109 -3.8291 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7606 -0.9611 -2.2302 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6370 -1.7865 -2.3035 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5714 -2.2567 0.3087 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3809 -1.8795 -0.7597 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3840 -2.7087 1.4991 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2348 -3.7184 1.1119 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1096 -1.5012 2.0375 C 0 0 2 0 0 0 0 0 0 0 0 0 9.5078 -1.6596 3.3535 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6480 2.0128 -0.7727 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5123 0.3828 2.7716 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6877 -1.6987 1.1027 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4339 -1.0654 -0.1474 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8022 1.3423 0.2607 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5819 1.3733 1.8933 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2824 0.8403 4.6228 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6786 1.1449 4.0047 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5750 0.7546 3.4802 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8836 0.4184 2.7427 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6893 -0.0548 2.0104 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8655 -1.1290 -1.2924 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3084 -3.3857 -2.9399 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0442 -0.2082 -2.2247 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5202 0.5393 -0.8659 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6085 2.0388 -1.1288 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4383 1.9956 -1.8286 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2752 2.0862 0.9804 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8901 0.3844 2.0187 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9057 -0.2410 -2.1858 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2274 0.3160 -0.5132 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4285 0.5220 -0.8127 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9758 1.2634 -2.5642 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9856 2.5471 -6.0034 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0704 -0.2846 -4.1587 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1928 1.3208 -3.6058 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6338 -1.6210 -2.5036 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8971 -1.2278 -2.6688 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9953 -3.1402 -0.0325 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1761 -2.3831 -1.5870 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6775 -3.0584 2.2777 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7456 -4.5782 1.0818 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0663 -1.4341 1.4395 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2406 -1.0509 3.6000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 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 2 0 12 13 1 0 13 14 1 0 13 15 2 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 27 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 23 37 1 0 37 38 1 0 37 39 2 0 19 40 1 0 40 41 1 0 41 42 2 0 9 43 1 0 43 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 44 48 1 0 48 49 1 0 48 50 1 0 50 51 1 0 6 52 1 0 52 53 1 0 52 54 1 0 54 55 1 0 54 56 1 0 56 57 1 0 56 4 1 0 50 8 1 0 42 11 1 0 41 15 1 0 39 20 1 0 35 25 1 0 3 58 1 0 4 59 1 1 6 60 1 1 8 61 1 1 9 62 1 1 12 63 1 0 14 64 1 0 18 65 1 0 21 66 1 0 22 67 1 0 25 68 1 1 27 69 1 6 30 70 1 0 31 71 1 6 32 72 1 0 33 73 1 6 34 74 1 0 35 75 1 1 36 76 1 0 38 77 1 0 39 78 1 0 42 79 1 0 44 80 1 1 47 81 1 0 48 82 1 6 49 83 1 0 50 84 1 6 51 85 1 0 52 86 1 6 53 87 1 0 54 88 1 1 55 89 1 0 56 90 1 6 57 91 1 0 M END

Standard InCHIKey	AEYXZGCDWDUIKX-VLAQAZPLSA-N
Standard InCHI	InChI=1S/C33H34O24/c34-9-3-7(1-2-12(9)53-31-22(43)16(37)18(39)24(54-31)28(45)46)13-6-11(36)15-10(35)4-8(5-14(15)52-13)51-33-27(21(42)20(41)26(56-33)30(49)50)57-32-23(44)17(38)19(40)25(55-32)29(47)48/h1-6,16-27,31-35,37-44H,(H,45,46)(H,47,48)(H,49,50)/t16-,17-,18-,19-,20-,21-,22+,23-,24+,25-,26+,27+,31+,32-,33+/m0/s1
SMILES	O=C(O)[C@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C=C(C5=CC=C(O[C@@H]6O[C@@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]6O)C(O)=C5)OC4=C3)O[C@@H](C(=O)O)[C@@H](O)[C@@H]2O)[C@@H](O)[C@@H](O)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	814.14	Volume:	709.95 ? Van der Waals volume.
Dense:	1.147	LogP:	-1.523 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.286 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.149 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	39.0
TPSA:	399.79 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	13.0	Rings:	6.0
Heavy Atoms:	24.0

MedChem Properties

QED Drug-Likeness Score:	0.091	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.513	Fsp³:	0.455
MCE-18:	163.125 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.482	Fluc inhibitor:	0.391 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.923 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.65 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.516	Promiscuous compounds:	0.529

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.626	MDCK Permeability:	-4.907
Pgp-inhibitor:	0.0	Pgp-substrate:	0.711
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):	0.378
20% Bioavailability (F20%):	0.011	30% Bioavailability (F30%):	0.062
50% Bioavailability (F50%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	58.51%	Volume Distribution (VD):	-0.408
Fu:	34.729% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.026	BCRP inhibitor:	0.0
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:	0.077
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):

-0.18

Half-life (T1/2):

7.328

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.263	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.651	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	0.999
Carcinogencity:	0.0	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.989
Hematotoxicity:	0.058	Drug-induced Nephrotoxicity:	0.98
Genotoxicity:	0.976	RPMI-8226 Immunitoxicity:	0.115
A549 Cytotoxicity:	0.001	Hek293 Cytotoxicity:	0.004
BCF:	0.134 ? 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:	2.614 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.163 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.383 ? 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
NPO659	Secale cereale	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21381697]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9134744]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO659	Secale cereale	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO659	Secale cereale	Species	Poaceae	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

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

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 NPC505807 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	22879
0.1-0.2	24690
0.2-0.3	1647
0.3-0.4	485
0.4-0.5	113
0.5-0.6	35
0.6-0.7	3
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	Natural Product ID
0.7273	Intermediate Similarity	NPC253685
0.7033	Intermediate Similarity	NPC20505
0.6957	Remote Similarity	NPC608742
0.6915	Remote Similarity	NPC600989
0.6667	Remote Similarity	NPC282169
0.5918	Remote Similarity	NPC22832
0.5755	Remote Similarity	NPC209296
0.5686	Remote Similarity	NPC8856
0.5657	Remote Similarity	NPC237435
0.5607	Remote Similarity	NPC229409
0.56	Remote Similarity	NPC43211
0.5472	Remote Similarity	NPC115674
0.547	Remote Similarity	NPC198199
0.5462	Remote Similarity	NPC120952
0.5421	Remote Similarity	NPC46202
0.5408	Remote Similarity	NPC19709
0.5354	Remote Similarity	NPC189142
0.5354	Remote Similarity	NPC77660
0.5347	Remote Similarity	NPC135277
0.5294	Remote Similarity	NPC115760
0.5294	Remote Similarity	NPC601144
0.5278	Remote Similarity	NPC64051
0.5238	Remote Similarity	NPC606546
0.5234	Remote Similarity	NPC210073
0.52	Remote Similarity	NPC95090
0.52	Remote Similarity	NPC27408
0.5196	Remote Similarity	NPC191306
0.5196	Remote Similarity	NPC285197
0.5192	Remote Similarity	NPC190003
0.5175	Remote Similarity	NPC11468
0.5152	Remote Similarity	NPC473043
0.5149	Remote Similarity	NPC181712
0.5135	Remote Similarity	NPC479766
0.5098	Remote Similarity	NPC101191
0.5093	Remote Similarity	NPC22062
0.5093	Remote Similarity	NPC65003
0.5093	Remote Similarity	NPC473634
0.5093	Remote Similarity	NPC138811
0.5089	Remote Similarity	NPC195257
0.5049	Remote Similarity	NPC210094

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC505807 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4568
0.1-0.2	4521
0.2-0.3	50
0.3-0.4	8
0.4-0.5	1
0.5-0.6	2
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
0.5755	Remote Similarity	NPD7054	Phase 4
0.5657	Remote Similarity	NPD4338	Clinical (unspecified phase)

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