NPASS Compound

Natural Product: NPC544627

Natural Product ID	NPC544627
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-2-[3-hydroxy-4-[(3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-2-[3-hydroxy-4-[(3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
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 94 99 0 0 0 0 0 0 0 0999 V2000 1.8740 -2.9599 -4.5326 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8276 -2.4426 -3.4062 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8901 -1.8073 -2.7975 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7717 -1.2554 -1.5485 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8772 -0.5755 -0.8699 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1213 -0.4192 -1.4322 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1757 0.2220 -0.7618 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0072 0.7278 0.5018 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9591 1.3703 1.2503 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2426 1.6145 0.7977 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6270 2.9606 0.9692 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7047 3.2488 0.1723 C 0 0 2 0 0 0 0 0 0 0 0 0 9.1760 3.6716 -1.1983 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3804 4.7984 -0.9711 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6501 2.1110 -0.0268 C 0 0 1 0 0 0 0 0 0 0 0 0 11.9349 2.6624 -0.2038 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6771 1.1655 1.1564 C 0 0 2 0 0 0 0 0 0 0 0 0 11.3557 0.0235 0.7371 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2907 0.8060 1.5646 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0761 0.8705 2.9197 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7402 0.5680 1.0716 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5341 1.0657 2.3426 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7149 -0.0640 0.4009 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6189 -1.3429 -0.9372 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5533 -1.9430 -1.4694 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6203 -1.9879 -0.7528 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7788 -2.6027 -1.2496 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9005 -2.6035 -0.4807 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1307 -3.1760 -0.7714 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0434 -2.1937 -1.1498 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2785 -2.3734 -0.5283 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3839 -1.5608 -1.1186 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2471 -0.2434 -1.1695 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1752 0.6013 -0.1473 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2505 1.5476 -0.1400 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0270 2.3458 0.9802 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2973 2.9103 1.5704 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9408 3.6810 2.6746 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0411 3.4565 0.6580 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2222 3.7337 1.7325 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1630 2.8959 -0.4532 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8953 3.0319 -1.6320 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9036 1.4419 -0.1260 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3494 1.3867 1.1482 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1861 -2.3566 0.9496 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4580 -2.4953 1.4959 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3447 -3.5431 1.4194 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4986 -3.0695 2.4280 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5750 -4.1112 0.2889 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1749 -5.2709 -0.2381 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6464 -3.1564 -2.5095 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4824 -3.1186 -3.2356 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3944 -3.6931 -4.5082 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6353 -2.5061 -2.7160 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8291 -1.7556 -3.3377 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3084 -0.7971 -2.4250 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1375 0.3139 -1.2567 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4350 1.3719 -0.2649 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2460 4.1177 0.6347 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5460 2.8797 -1.6039 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0388 3.9220 -1.8531 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4273 4.5951 -1.0258 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3418 1.5367 -0.9183 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2814 3.0197 0.6351 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2911 1.5858 1.9955 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9114 -0.3822 -0.0744 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0948 -0.2589 1.2435 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0522 -0.0185 3.3722 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8100 0.6315 3.2062 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7206 -0.1828 0.8611 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6763 -1.5449 0.2205 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0257 -3.8053 -1.7147 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5027 -3.4895 -0.7793 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5746 -2.0301 -2.1364 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3444 -1.8618 -0.5640 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2896 0.0977 0.8264 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5718 1.7036 1.7588 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8042 3.6170 0.8491 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9643 2.1194 1.9060 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0998 3.3911 3.0828 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5952 4.3468 0.2842 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6927 4.5520 1.5114 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1915 3.4130 -0.5310 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8046 3.3941 -1.4961 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1334 1.0084 -0.8103 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6143 2.0399 1.2617 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7246 -1.4188 1.3607 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4515 -2.8399 2.4303 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0059 -4.2911 1.9181 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1006 -2.7480 3.1700 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6060 -4.5286 0.7403 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7642 -5.3835 -1.1439 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5144 -3.6475 -2.9508 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4255 -4.7202 -4.5456 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 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 12 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 8 21 1 0 21 22 1 0 21 23 2 0 4 24 1 0 24 25 1 0 25 26 2 0 26 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 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 31 45 1 0 45 46 1 0 45 47 1 0 47 48 1 0 47 49 1 0 49 50 1 0 27 51 2 0 51 52 1 0 52 53 1 0 52 54 2 0 54 2 1 0 23 5 1 0 54 25 1 0 19 10 1 0 49 29 1 0 43 34 1 0 3 55 1 0 6 56 1 0 7 57 1 0 10 58 1 0 12 59 1 1 13 60 1 0 13 61 1 0 14 62 1 0 15 63 1 6 16 64 1 0 17 65 1 1 18 66 1 0 19 67 1 6 20 68 1 0 22 69 1 0 23 70 1 0 26 71 1 0 29 72 1 6 31 73 1 1 32 74 1 0 32 75 1 0 34 76 1 1 36 77 1 1 37 78 1 0 37 79 1 0 38 80 1 0 39 81 1 6 40 82 1 0 41 83 1 6 42 84 1 0 43 85 1 6 44 86 1 0 45 87 1 6 46 88 1 0 47 89 1 1 48 90 1 0 49 91 1 1 50 92 1 0 51 93 1 0 53 94 1 0 M END

Standard InCHIKey	QULQFSQMGIQIPK-QTEAGBNPSA-N
Standard InCHI	InChI=1S/C33H40O21/c34-7-18-22(39)25(42)28(45)31(52-18)48-9-20-24(41)27(44)29(46)32(54-20)49-11-4-13(37)21-14(38)6-16(50-17(21)5-11)10-1-2-15(12(36)3-10)51-33-30(47)26(43)23(40)19(8-35)53-33/h1-6,18-20,22-37,39-47H,7-9H2/t18-,19-,20-,22-,23-,24-,25+,26+,27+,28-,29-,30-,31-,32-,33?/m1/s1
SMILES	O=C1C=C(C2=CC=C(OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(O)=C2)OC2=CC(O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)=CC(O)=C12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	772.21	Volume:	691.488 ? Van der Waals volume.
Dense:	1.117	LogP:	-0.828 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.181 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.137 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	36.0
TPSA:	348.58 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	13.0	Rings:	6.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.092	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.353	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:	1	PAINS Alert:	0
Colloidal aggregators:	0.633	Fluc inhibitor:	0.303 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.963 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.638 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.282	Promiscuous compounds:	0.423

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.124	MDCK Permeability:	-4.774
Pgp-inhibitor:	0.0	Pgp-substrate:	0.836
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):	0.998
20% Bioavailability (F20%):	0.219	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.011
Plasma Protein Binding (PPB):	71.402%	Volume Distribution (VD):	-0.221
Fu:	27.425% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.043
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:	0.097
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):

0.85

Half-life (T1/2):

6.527

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.008
Human Hepatotoxicity (H-HT):	0.609	Drug-induced Liver Injury (DILI):	0.992
AMES Toxicity:	0.989	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.043	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.135	Drug-induced Nephrotoxicity:	0.856
Genotoxicity:	0.708	RPMI-8226 Immunitoxicity:	0.237
A549 Cytotoxicity:	0.652	Hek293 Cytotoxicity:	0.324
BCF:	0.256 ? 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:	2.497 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.296 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.243 ? 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
NPO19153	Launaea nudicaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19153	Launaea nudicaulis	Species	Asteraceae	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 NPC544627 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	22622
0.1-0.2	22888
0.2-0.3	3156
0.3-0.4	751
0.4-0.5	284
0.5-0.6	100
0.6-0.7	37
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
0.8182	Intermediate Similarity	NPC209296
0.7952	Intermediate Similarity	NPC22832
0.7333	Intermediate Similarity	NPC22062
0.7333	Intermediate Similarity	NPC473634
0.7333	Intermediate Similarity	NPC210073
0.7333	Intermediate Similarity	NPC138811
0.7228	Intermediate Similarity	NPC198199
0.7059	Intermediate Similarity	NPC95090
0.7059	Intermediate Similarity	NPC27408
0.7059	Intermediate Similarity	NPC189142
0.7059	Intermediate Similarity	NPC77660
0.7033	Intermediate Similarity	NPC44931
0.7019	Intermediate Similarity	NPC120952
0.7011	Intermediate Similarity	NPC285197
0.6932	Remote Similarity	NPC601144
0.6915	Remote Similarity	NPC65711
0.6842	Remote Similarity	NPC473623
0.6818	Remote Similarity	NPC191306
0.6771	Remote Similarity	NPC488089
0.6744	Remote Similarity	NPC261866
0.6744	Remote Similarity	NPC39360
0.6744	Remote Similarity	NPC29763
0.6744	Remote Similarity	NPC210003
0.6742	Remote Similarity	NPC243930
0.6742	Remote Similarity	NPC486578
0.6742	Remote Similarity	NPC605067
0.6667	Remote Similarity	NPC311830
0.6667	Remote Similarity	NPC275454
0.6667	Remote Similarity	NPC607707
0.6505	Remote Similarity	NPC311850
0.6452	Remote Similarity	NPC251417
0.6442	Remote Similarity	NPC488083
0.6327	Remote Similarity	NPC229409
0.6321	Remote Similarity	NPC68592
0.63	Remote Similarity	NPC101636
0.6289	Remote Similarity	NPC46202
0.6277	Remote Similarity	NPC8856
0.6262	Remote Similarity	NPC298666
0.6122	Remote Similarity	NPC64051
0.6117	Remote Similarity	NPC11468
0.61	Remote Similarity	NPC270675
0.61	Remote Similarity	NPC195685
0.6095	Remote Similarity	NPC480441
0.6095	Remote Similarity	NPC25523
0.6082	Remote Similarity	NPC479405
0.6064	Remote Similarity	NPC190003
0.6044	Remote Similarity	NPC181712
0.602	Remote Similarity	NPC204693
0.602	Remote Similarity	NPC479404
0.6	Remote Similarity	NPC289667
0.6	Remote Similarity	NPC19709
0.5982	Remote Similarity	NPC262222
0.598	Remote Similarity	NPC298171
0.5979	Remote Similarity	NPC67105
0.5922	Remote Similarity	NPC472994
0.5922	Remote Similarity	NPC135358
0.59	Remote Similarity	NPC479403
0.5882	Remote Similarity	NPC475382
0.587	Remote Similarity	NPC58716
0.5859	Remote Similarity	NPC115674
0.5859	Remote Similarity	NPC186816
0.5849	Remote Similarity	NPC472993
0.5842	Remote Similarity	NPC483707
0.5833	Remote Similarity	NPC488087
0.5824	Remote Similarity	NPC58053
0.5824	Remote Similarity	NPC143851
0.5816	Remote Similarity	NPC227508
0.5806	Remote Similarity	NPC27942
0.5794	Remote Similarity	NPC473644
0.5761	Remote Similarity	NPC277205
0.5761	Remote Similarity	NPC37919
0.5714	Remote Similarity	NPC473043
0.5714	Remote Similarity	NPC331652
0.5699	Remote Similarity	NPC186807
0.5652	Remote Similarity	NPC45618
0.5638	Remote Similarity	NPC21100
0.56	Remote Similarity	NPC65003
0.5591	Remote Similarity	NPC297987
0.5591	Remote Similarity	NPC168822
0.5591	Remote Similarity	NPC146792
0.5591	Remote Similarity	NPC136042
0.5591	Remote Similarity	NPC323593
0.5591	Remote Similarity	NPC203500
0.5586	Remote Similarity	NPC488086
0.5577	Remote Similarity	NPC195257
0.5577	Remote Similarity	NPC256760
0.5567	Remote Similarity	NPC601586
0.5542	Remote Similarity	NPC223579
0.5532	Remote Similarity	NPC84362
0.5532	Remote Similarity	NPC45638
0.5521	Remote Similarity	NPC80188
0.5521	Remote Similarity	NPC601710
0.551	Remote Similarity	NPC211594
0.5474	Remote Similarity	NPC201292
0.5464	Remote Similarity	NPC220169
0.5455	Remote Similarity	NPC254540
0.5455	Remote Similarity	NPC277532
0.5446	Remote Similarity	NPC156869
0.5417	Remote Similarity	NPC60735
0.5417	Remote Similarity	NPC26230
0.5417	Remote Similarity	NPC609451
0.5417	Remote Similarity	NPC611303
0.54	Remote Similarity	NPC295613
0.54	Remote Similarity	NPC473657
0.5385	Remote Similarity	NPC473327
0.5361	Remote Similarity	NPC284960
0.5361	Remote Similarity	NPC609478
0.5351	Remote Similarity	NPC470719
0.534	Remote Similarity	NPC488073
0.534	Remote Similarity	NPC64425
0.534	Remote Similarity	NPC475366
0.5327	Remote Similarity	NPC253685
0.5306	Remote Similarity	NPC88023
0.5306	Remote Similarity	NPC116458
0.5306	Remote Similarity	NPC246943
0.5306	Remote Similarity	NPC309025
0.5306	Remote Similarity	NPC602805
0.5306	Remote Similarity	NPC605784
0.5294	Remote Similarity	NPC473512
0.5294	Remote Similarity	NPC129827
0.5294	Remote Similarity	NPC102028
0.5294	Remote Similarity	NPC303913
0.5294	Remote Similarity	NPC3583
0.5278	Remote Similarity	NPC14187
0.5263	Remote Similarity	NPC93337
0.5258	Remote Similarity	NPC307938
0.5243	Remote Similarity	NPC122809
0.5222	Remote Similarity	NPC191154
0.5221	Remote Similarity	NPC488088
0.5208	Remote Similarity	NPC105025
0.5204	Remote Similarity	NPC21666
0.52	Remote Similarity	NPC172807
0.5192	Remote Similarity	NPC284277
0.5192	Remote Similarity	NPC475497
0.5185	Remote Similarity	NPC484301
0.5165	Remote Similarity	NPC134819
0.5149	Remote Similarity	NPC606546
0.5146	Remote Similarity	NPC218488
0.514	Remote Similarity	NPC80068
0.514	Remote Similarity	NPC477629
0.5104	Remote Similarity	NPC234739
0.5098	Remote Similarity	NPC187379
0.5094	Remote Similarity	NPC35119
0.5093	Remote Similarity	NPC287889
0.5089	Remote Similarity	NPC470715
0.5089	Remote Similarity	NPC164704
0.5052	Remote Similarity	NPC73511
0.5052	Remote Similarity	NPC610763
0.5051	Remote Similarity	NPC120099
0.5047	Remote Similarity	NPC142142
0.5047	Remote Similarity	NPC479766

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC544627 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5508
0.1-0.2	3555
0.2-0.3	73
0.3-0.4	6
0.4-0.5	4
0.5-0.6	2
0.6-0.7	1
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	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD7054	Phase 4
0.6275	Remote Similarity	NPD7472	Pre-clinical
0.566	Remote Similarity	NPD7808	Phase 3
0.5577	Remote Similarity	NPD7251	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