NPASS Compound

Natural Product: NPC507436

Natural Product ID	NPC507436
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[4-[5-hydroxy-4-oxo-7-[(2~{S},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-2-yl]phenyl] (~{E})-3-(3,4-dihydroxyphenyl)prop-2-enoate
IUPAC Name	[4-[5-hydroxy-4-oxo-7-[(2~{S},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-2-yl]phenyl] (~{E})-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 89 94 0 0 0 0 0 0 0 0999 V2000 -11.6284 -0.3335 -0.6042 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3998 -0.8087 0.1380 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.5152 -1.3291 -0.8058 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2988 -1.7183 -0.1240 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8362 -0.7259 0.6111 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7635 -0.0015 0.5791 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4196 -0.5758 0.7989 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4356 0.4190 0.8355 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8421 0.8534 -0.2805 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4489 0.7432 -0.1051 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4920 1.7266 -0.1360 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7596 3.0515 -0.3897 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7607 4.0143 -0.4108 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0512 5.3520 -0.6693 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5412 3.6712 -0.1766 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5730 4.5731 -0.1826 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2968 5.7788 -0.4190 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8526 4.1397 0.0651 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1002 2.8218 0.3156 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4509 2.3253 0.5840 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5409 3.1235 0.6082 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8035 2.6119 0.8756 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9894 1.2734 1.1257 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2415 0.7647 1.3915 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0593 0.2888 0.3995 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6373 0.3263 -0.7910 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3991 -0.2552 0.7148 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1636 -0.7082 -0.2370 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4906 -1.2608 -0.0336 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0839 -1.3703 1.1885 C 0 0 0 0 0 0 0 0 0 0 0 0 14.3659 -1.9135 1.3290 C 0 0 0 0 0 0 0 0 0 0 0 0 15.0545 -2.3500 0.2269 C 0 0 0 0 0 0 0 0 0 0 0 0 16.3358 -2.8937 0.3627 O 0 0 0 0 0 0 0 0 0 0 0 0 14.4797 -2.2521 -1.0209 C 0 0 0 0 0 0 0 0 0 0 0 0 15.1593 -2.6902 -2.1664 O 0 0 0 0 0 0 0 0 0 0 0 0 13.2102 -1.7104 -1.1301 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8783 0.4600 1.1008 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6118 0.9632 0.8339 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0895 1.9983 0.3112 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8290 2.3393 0.0814 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1584 1.3914 0.1012 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1659 0.2403 -1.6078 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9701 1.1125 -2.3227 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8483 -1.0959 -1.5453 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1442 -2.0251 -2.3036 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8919 -1.6052 -0.1232 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4485 -2.8246 0.0497 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6743 -2.9312 0.7315 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2816 -3.8502 -0.1083 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6204 -2.4170 1.7999 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9730 -1.3612 2.4463 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8362 -1.8633 1.1308 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.6364 -1.2536 2.0828 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.6193 0.7822 -0.6977 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5450 -0.6211 -0.0470 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6636 -0.7960 -1.6094 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9256 0.0215 0.6913 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7002 -2.0992 -0.9680 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7848 0.6188 -0.3895 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8371 0.8393 1.3926 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4163 -1.0062 1.8411 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0532 1.9776 -0.3421 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7852 3.3990 -0.5890 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0460 6.0811 0.0071 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6539 4.8701 0.0552 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4986 4.1851 0.4254 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6769 3.2561 0.8937 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7107 -0.2653 1.7267 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7541 -0.6553 -1.2498 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5362 -1.0245 2.0601 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8136 -1.9890 2.3076 H 0 0 0 0 0 0 0 0 0 0 0 0 16.4288 -3.8983 0.1541 H 0 0 0 0 0 0 0 0 0 0 0 0 16.1669 -2.7608 -2.1016 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7371 -1.6256 -2.1123 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0428 -0.5982 1.2997 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7804 0.2811 0.8278 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0789 0.3568 0.3023 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2264 0.1430 -2.2311 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5974 2.0357 -2.1570 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8748 -1.0490 -1.9330 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2229 -1.7228 -2.4676 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7901 -1.7358 0.1659 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9657 -3.3776 0.7139 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7894 -3.3195 1.2217 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9105 -3.7682 -1.0288 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8309 -3.2655 2.4813 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5068 -0.9976 3.1697 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3607 -2.6694 0.5913 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3639 -1.8411 2.4128 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 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 2 0 25 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 2 0 23 37 1 0 37 38 2 0 19 39 1 0 39 40 1 0 40 41 2 0 9 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 4 48 1 0 48 49 1 0 48 50 1 0 50 51 1 0 50 52 1 0 52 53 1 0 52 2 1 0 46 7 1 0 41 11 1 0 40 15 1 0 38 20 1 0 36 29 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 1 4 58 1 6 6 59 1 0 6 60 1 0 7 61 1 1 9 62 1 6 12 63 1 0 14 64 1 0 18 65 1 0 21 66 1 0 22 67 1 0 27 68 1 0 28 69 1 0 30 70 1 0 31 71 1 0 33 72 1 0 35 73 1 0 36 74 1 0 37 75 1 0 38 76 1 0 41 77 1 0 42 78 1 6 43 79 1 0 44 80 1 6 45 81 1 0 46 82 1 1 47 83 1 0 48 84 1 1 49 85 1 0 50 86 1 1 51 87 1 0 52 88 1 6 53 89 1 0 M END

Standard InCHIKey	VFFCBWDFYBEZAX-AODTUXATSA-N
Standard InCHI	InChI=1S/C36H36O17/c1-15-29(42)31(44)33(46)35(49-15)48-14-26-30(43)32(45)34(47)36(53-26)51-19-11-22(39)28-23(40)13-24(52-25(28)12-19)17-4-6-18(7-5-17)50-27(41)9-3-16-2-8-20(37)21(38)10-16/h2-13,15,26,29-39,42-47H,14H2,1H3/b9-3+/t15-,26-,29-,30+,31-,32-,33+,34+,35+,36+/m0/s1
SMILES	C[C@@H]1O[C@@H](OC[C@@H]2O[C@@H](OC3=CC(O)=C4C(=O)C=C(C5=CC=C(OC(=O)/C=C/C6=CC=C(O)C(O)=C6)C=C5)OC4=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	740.2	Volume:	695.033 ? Van der Waals volume.
Dense:	1.065	LogP:	1.503 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.653 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.44 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	38.0
TPSA:	275.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	9.0	Rings:	6.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.048	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.952	Fsp³:	0.333
MCE-18:	136.667 ? 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:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.693	Fluc inhibitor:	0.78 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.98 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.994 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.232	Promiscuous compounds:	0.458

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.386	MDCK Permeability:	-5.252
Pgp-inhibitor:	0.0	Pgp-substrate:	0.136
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):	0.975
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.034
Plasma Protein Binding (PPB):	86.132%	Volume Distribution (VD):	-0.055
Fu:	10.614% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.018
BSEP inhibitor:	0.082

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:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

1.233

Half-life (T1/2):

4.907

ADMET: Toxicity

hERG Blockers:	0.031	hERG Blockers (10um):	0.324
Human Hepatotoxicity (H-HT):	0.375	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.876	Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.208	Skin Sensitization:	0.998
Carcinogencity:	0.03	Eye Corrosion:	0.0
Eye Irritation:	0.307	Respiratory Toxicity:	0.022
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.949
Hematotoxicity:	0.025	Drug-induced Nephrotoxicity:	0.336
Genotoxicity:	0.879	RPMI-8226 Immunitoxicity:	0.118
A549 Cytotoxicity:	0.945	Hek293 Cytotoxicity:	0.705
BCF:	0.94 ? 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:	3.746 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.153 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.677 ? 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
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11240-011-0014-8]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36365393]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37959863]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38370080]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39141828]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39401641]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39633960]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30828	Mentha piperita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

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 NPC507436 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	17373
0.1-0.2	28112
0.2-0.3	3326
0.3-0.4	721
0.4-0.5	246
0.5-0.6	60
0.6-0.7	12
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	Natural Product ID
0.7604	Intermediate Similarity	NPC22062
0.7604	Intermediate Similarity	NPC473634
0.7604	Intermediate Similarity	NPC138811
0.732	Intermediate Similarity	NPC44931
0.7245	Intermediate Similarity	NPC210073
0.7129	Intermediate Similarity	NPC209296
0.6731	Remote Similarity	NPC270675
0.6731	Remote Similarity	NPC195685
0.6476	Remote Similarity	NPC473623
0.6415	Remote Similarity	NPC488089
0.6389	Remote Similarity	NPC472994
0.6346	Remote Similarity	NPC204693
0.6306	Remote Similarity	NPC472993
0.6296	Remote Similarity	NPC101636
0.6273	Remote Similarity	NPC11468
0.6154	Remote Similarity	NPC67105
0.6075	Remote Similarity	NPC65711
0.6053	Remote Similarity	NPC311850
0.5965	Remote Similarity	NPC473644
0.5946	Remote Similarity	NPC484301
0.5918	Remote Similarity	NPC331652
0.5909	Remote Similarity	NPC477629
0.5897	Remote Similarity	NPC68592
0.5888	Remote Similarity	NPC186816
0.5859	Remote Similarity	NPC19709
0.5856	Remote Similarity	NPC298171
0.5849	Remote Similarity	NPC227508
0.5847	Remote Similarity	NPC298666
0.5833	Remote Similarity	NPC46202
0.5766	Remote Similarity	NPC475382
0.5727	Remote Similarity	NPC229409
0.5714	Remote Similarity	NPC198199
0.5688	Remote Similarity	NPC64051
0.5648	Remote Similarity	NPC303913
0.5644	Remote Similarity	NPC95090
0.5644	Remote Similarity	NPC27408
0.5625	Remote Similarity	NPC80068
0.561	Remote Similarity	NPC262222
0.56	Remote Similarity	NPC473043
0.5588	Remote Similarity	NPC181712
0.5574	Remote Similarity	NPC120952
0.5505	Remote Similarity	NPC65003
0.55	Remote Similarity	NPC488086
0.5472	Remote Similarity	NPC190003
0.5462	Remote Similarity	NPC488087
0.5462	Remote Similarity	NPC488083
0.5455	Remote Similarity	NPC115674
0.5446	Remote Similarity	NPC483707
0.5424	Remote Similarity	NPC480441
0.5405	Remote Similarity	NPC475366
0.5392	Remote Similarity	NPC39360
0.5392	Remote Similarity	NPC29763
0.5392	Remote Similarity	NPC210003
0.5385	Remote Similarity	NPC27942
0.534	Remote Similarity	NPC189142
0.534	Remote Similarity	NPC77660
0.5321	Remote Similarity	NPC187379
0.5294	Remote Similarity	NPC25523
0.5283	Remote Similarity	NPC22832
0.5278	Remote Similarity	NPC211594
0.5273	Remote Similarity	NPC275454
0.5259	Remote Similarity	NPC135358
0.5217	Remote Similarity	NPC195257
0.521	Remote Similarity	NPC480796
0.521	Remote Similarity	NPC473278
0.5175	Remote Similarity	NPC210961
0.514	Remote Similarity	NPC243930
0.514	Remote Similarity	NPC601144
0.5109	Remote Similarity	NPC482520
0.5109	Remote Similarity	NPC482519
0.5093	Remote Similarity	NPC311830
0.5093	Remote Similarity	NPC607707
0.5089	Remote Similarity	NPC479405
0.5085	Remote Similarity	NPC603856
0.5045	Remote Similarity	NPC295613
0.5045	Remote Similarity	NPC473657
0.5044	Remote Similarity	NPC479404
0.5042	Remote Similarity	NPC599948

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC507436 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4335
0.1-0.2	4737
0.2-0.3	68
0.3-0.4	5
0.4-0.5	1
0.5-0.6	3
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
0.7129	Intermediate Similarity	NPD7054	Phase 4
0.5625	Remote Similarity	NPD7251	Phase 2
0.5431	Remote Similarity	NPD7472	Pre-clinical
0.5431	Remote Similarity	NPD7808	Phase 3

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