NPASS Compound

Natural Product: NPC586403

Natural Product ID	NPC586403
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{S},3~{S},4~{S},5~{R},6~{S})-6-[4-[7-[(2~{S},3~{S},4~{S},5~{S},6~{R})-6-carboxy-4,5-dihydroxy-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-4-oxo-chromen-2-yl]phenoxy]-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
IUPAC Name	(2~{S},3~{S},4~{S},5~{R},6~{S})-6-[4-[7-[(2~{S},3~{S},4~{S},5~{S},6~{R})-6-carboxy-4,5-dihydroxy-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-4-oxo-chromen-2-yl]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]

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 8.7203 4.3461 -3.6096 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5234 3.9265 -2.7537 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6293 4.6802 -2.4293 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2884 2.6349 -2.0968 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1257 2.0290 -2.5599 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7790 1.0355 -1.6227 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5152 0.5581 -1.9150 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4917 0.4531 -1.0097 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2393 -0.0088 -1.4267 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1887 -0.1330 -0.5615 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3187 0.1970 0.7843 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1580 0.0447 1.6790 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2586 0.3253 3.0112 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1746 0.1872 3.8806 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2399 0.4353 5.0950 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0313 -0.2488 3.3562 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1457 -0.4069 4.1660 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0567 -0.1260 5.5220 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3325 -0.8478 3.5853 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4067 -1.1213 2.2465 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5637 -1.5538 1.6638 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7992 -1.7937 2.2136 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1093 -3.1656 2.0908 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7931 -3.4743 0.9389 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8853 -4.9601 0.8576 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4049 -5.7366 1.7175 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5393 -5.5201 -0.2294 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2011 -2.8803 0.9154 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0680 -3.8561 1.4108 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1906 -1.7425 1.9090 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3193 -0.9616 1.8550 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9176 -0.9398 1.5981 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6952 -0.9157 0.2527 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5590 0.3186 -0.3236 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5153 0.5662 -1.3066 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3066 1.8183 -1.8703 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4722 2.1478 -2.7972 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5656 1.1967 -3.8113 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0508 1.8477 -2.7330 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1516 2.8300 -2.2880 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3606 0.5134 -2.5283 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1527 -0.5093 -3.0433 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2095 0.3607 -1.0083 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4289 1.4261 -0.5624 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2710 -0.9509 1.4721 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0692 -0.5156 2.0027 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9996 -0.3637 1.2301 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5292 0.6507 1.2190 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5778 0.7672 0.3202 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7940 -0.1047 -1.6806 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4520 -1.0063 -0.6935 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1776 0.4674 -1.4368 C 0 0 1 0 0 0 0 0 0 0 0 0 11.1640 -0.4844 -1.6223 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4322 1.6631 -2.3272 C 0 0 2 0 0 0 0 0 0 0 0 0 11.6565 2.2192 -1.9969 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9555 5.4768 -2.9863 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1442 2.7737 -0.9857 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8950 1.4857 -0.6210 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1518 -0.2639 -2.4832 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2075 -0.4961 -0.8962 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1775 0.6718 3.4880 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6316 -0.8474 6.1054 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1961 -0.9635 4.2494 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8172 -1.6067 3.3216 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1883 -3.1702 0.0610 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7781 -6.4940 -0.3208 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4766 -2.5302 -0.0895 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6119 -4.2597 2.1965 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0972 -2.2099 2.9155 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7951 -0.9296 2.7271 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9595 0.0450 2.0832 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6568 1.0808 0.4907 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2333 2.5671 -1.0746 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2304 3.1113 -3.2813 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4395 2.1619 -2.2569 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4469 0.8017 -3.9051 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2751 2.0399 -3.7973 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5406 3.7319 -2.3585 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3666 0.4970 -2.9686 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9056 -0.7895 -3.9492 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6338 -0.5777 -0.8784 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6256 1.4377 -1.1448 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3198 -1.1642 0.4138 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6802 0.9243 2.2726 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5097 1.1314 0.7339 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7419 -0.6183 -2.6575 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9796 -1.8396 -0.7062 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2296 0.8004 -0.3682 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9006 -0.2874 -1.0004 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4078 1.2927 -3.3688 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3838 1.6989 -2.4162 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 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 2 0 17 18 1 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 24 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 1 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 36 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 20 45 1 0 45 46 2 0 46 47 1 0 11 48 1 0 48 49 2 0 6 50 1 0 50 51 1 0 50 52 1 0 52 53 1 0 52 54 1 0 54 55 1 0 54 4 1 0 49 8 1 0 47 12 1 0 46 16 1 0 32 22 1 0 43 34 1 0 3 56 1 0 4 57 1 1 6 58 1 1 9 59 1 0 10 60 1 0 13 61 1 0 18 62 1 0 19 63 1 0 22 64 1 1 24 65 1 6 27 66 1 0 28 67 1 6 29 68 1 0 30 69 1 1 31 70 1 0 32 71 1 1 34 72 1 1 36 73 1 1 37 74 1 0 37 75 1 0 38 76 1 0 39 77 1 6 40 78 1 0 41 79 1 6 42 80 1 0 43 81 1 6 44 82 1 0 45 83 1 0 48 84 1 0 49 85 1 0 50 86 1 6 51 87 1 0 52 88 1 1 53 89 1 0 54 90 1 6 55 91 1 0 M END

Standard InCHIKey	QHUYAVQUOQPHFT-PVAVAHCOSA-N
Standard InCHI	InChI=1S/C33H36O22/c34-8-16-18(37)19(38)24(43)32(52-16)55-28-23(42)22(41)27(30(47)48)54-33(28)50-11-5-12(35)17-13(36)7-14(51-15(17)6-11)9-1-3-10(4-2-9)49-31-25(44)20(39)21(40)26(53-31)29(45)46/h1-7,16,18-28,31-35,37-44H,8H2,(H,45,46)(H,47,48)/t16-,18-,19+,20+,21+,22+,23+,24-,25-,26+,27-,28+,31-,32+,33-/m1/s1
SMILES	O=C(O)[C@H]1O[C@@H](OC2=CC=C(C3=CC(=O)C4=C(O)C=C(O[C@@H]5O[C@@H](C(=O)O)[C@@H](O)[C@H](O)[C@@H]5O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C=C4O3)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	784.17	Volume:	695.006 ? Van der Waals volume.
Dense:	1.128	LogP:	-1.058 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.192 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.439 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	38.0
TPSA:	362.49 ? Topological Polar Surface Area.	H-Bond Acceptor:	22.0
H-Bond Donor:	12.0	Rings:	6.0
Heavy Atoms:	22.0

MedChem Properties

QED Drug-Likeness Score:	0.092	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.352	Fsp³:	0.485
MCE-18:	155.327 ? 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:	0.432	Fluc inhibitor:	0.508 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.924 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.652 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.483	Promiscuous compounds:	0.445

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.631	MDCK Permeability:	-4.893
Pgp-inhibitor:	0.0	Pgp-substrate:	0.967
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):	0.963
20% Bioavailability (F20%):	0.551	30% Bioavailability (F30%):	0.964
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.991
Plasma Protein Binding (PPB):	71.612%	Volume Distribution (VD):	-0.205
Fu:	25.583% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.003
OATP1B3 inhibitor:	0.156	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:	0.888
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):

0.296

Half-life (T1/2):

5.235

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.381	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.973	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.002	Eye Corrosion:	0.0
Eye Irritation:	0.005	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.993
Hematotoxicity:	0.327	Drug-induced Nephrotoxicity:	0.984
Genotoxicity:	0.891	RPMI-8226 Immunitoxicity:	0.278
A549 Cytotoxicity:	0.335	Hek293 Cytotoxicity:	0.099
BCF:	0.15 ? 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:	2.771 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.309 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.439 ? 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
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1104/pp.84.1.73]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12232319]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22208890]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18321	Medicago sativa	Species	Fabaceae	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 NPC586403 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	22532
0.1-0.2	23669
0.2-0.3	2938
0.3-0.4	487
0.4-0.5	157
0.5-0.6	59
0.6-0.7	12
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
0.7333	Intermediate Similarity	NPC608742
0.7273	Intermediate Similarity	NPC253685
0.6848	Remote Similarity	NPC282169
0.6667	Remote Similarity	NPC20505
0.6522	Remote Similarity	NPC95090
0.6522	Remote Similarity	NPC27408
0.6495	Remote Similarity	NPC8856
0.6139	Remote Similarity	NPC65003
0.6078	Remote Similarity	NPC115674
0.6064	Remote Similarity	NPC39360
0.6064	Remote Similarity	NPC29763
0.6064	Remote Similarity	NPC210003
0.6	Remote Similarity	NPC189142
0.6	Remote Similarity	NPC77660
0.5946	Remote Similarity	NPC311850
0.5943	Remote Similarity	NPC475382
0.5929	Remote Similarity	NPC68592
0.5918	Remote Similarity	NPC22832
0.5918	Remote Similarity	NPC243930
0.5893	Remote Similarity	NPC488083
0.5865	Remote Similarity	NPC46202
0.5758	Remote Similarity	NPC601144
0.5739	Remote Similarity	NPC298666
0.5729	Remote Similarity	NPC261866
0.5729	Remote Similarity	NPC143851
0.57	Remote Similarity	NPC607707
0.5648	Remote Similarity	NPC195257
0.5612	Remote Similarity	NPC181712
0.5607	Remote Similarity	NPC229409
0.56	Remote Similarity	NPC80188
0.5588	Remote Similarity	NPC600989
0.5586	Remote Similarity	NPC11468
0.5567	Remote Similarity	NPC58053
0.5566	Remote Similarity	NPC64051
0.5545	Remote Similarity	NPC311830
0.5534	Remote Similarity	NPC606546
0.5524	Remote Similarity	NPC22062
0.5524	Remote Similarity	NPC473634
0.5524	Remote Similarity	NPC138811
0.55	Remote Similarity	NPC262222
0.55	Remote Similarity	NPC237435
0.547	Remote Similarity	NPC198199
0.5462	Remote Similarity	NPC120952
0.5455	Remote Similarity	NPC186807
0.5446	Remote Similarity	NPC43211
0.5408	Remote Similarity	NPC289667
0.5357	Remote Similarity	NPC14187
0.5345	Remote Similarity	NPC488087
0.5327	Remote Similarity	NPC122809
0.5306	Remote Similarity	NPC331652
0.5304	Remote Similarity	NPC473644
0.5273	Remote Similarity	NPC479766
0.5253	Remote Similarity	NPC19709
0.5248	Remote Similarity	NPC27942
0.5182	Remote Similarity	NPC473623
0.5182	Remote Similarity	NPC35119
0.5152	Remote Similarity	NPC473043
0.514	Remote Similarity	NPC44931
0.5135	Remote Similarity	NPC488089
0.5126	Remote Similarity	NPC488086
0.5098	Remote Similarity	NPC101191
0.5096	Remote Similarity	NPC220169
0.5093	Remote Similarity	NPC210073
0.505	Remote Similarity	NPC277205
0.505	Remote Similarity	NPC37919
0.5049	Remote Similarity	NPC210094
0.5049	Remote Similarity	NPC285197
0.5048	Remote Similarity	NPC190003
0.5047	Remote Similarity	NPC603300
0.5045	Remote Similarity	NPC32641
0.5045	Remote Similarity	NPC256188
0.5045	Remote Similarity	NPC209296
0.5043	Remote Similarity	NPC480441

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC586403 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4505
0.1-0.2	4545
0.2-0.3	90
0.3-0.4	8
0.4-0.5	0
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
0.55	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.5045	Remote Similarity	NPD7054	Phase 4

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