NPASS Compound

Natural Product: NPC476470

Natural Product ID	NPC476470
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-Trihydroxy-6-Methyloxan-2-Yl]Oxymethyl]-3-[(2R,3S,4R,5S)-3,4,5-Trihydroxyoxan-2-Yl]Oxyoxan-2-Yl]Oxy-5,7-Dihydroxy-2-(4-Hydroxyphenyl)Chromen-4-One
IUPAC Name	3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]-3-[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL81853
PubChem CID	44460439
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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 89 94 0 0 0 0 0 0 0 0999 V2000 -4.0724 1.6896 4.6154 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7241 0.9243 3.5127 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6261 0.1723 2.7956 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2412 -0.5763 1.7032 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9144 -0.6092 1.2683 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0377 0.1393 1.9905 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4123 0.9036 3.0994 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5997 -1.4837 0.1462 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4900 -2.4206 -0.2026 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3452 -3.2676 -1.1673 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3232 -4.2170 -1.4688 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1886 -5.1249 -2.4884 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1871 -6.0709 -2.7723 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0504 -5.1271 -3.2686 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0756 -4.1943 -2.9819 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2127 -3.2781 -1.9522 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2593 -2.3468 -1.6562 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2151 -2.3228 -2.3461 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4649 -1.4439 -0.5967 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4523 -0.5053 -0.3694 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3565 0.6640 -1.1690 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6617 0.4531 -2.1331 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9172 0.4286 -1.6032 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4977 -0.9222 -1.3289 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7785 -0.8474 -0.7854 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3272 -2.0760 -0.5255 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6826 -2.2447 0.8118 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6126 -1.2897 1.2166 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6074 -1.1332 2.7258 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9685 -1.7394 0.7215 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7666 -2.6307 -0.4697 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5973 -2.2003 -1.3439 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4477 -3.2141 -2.3091 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6638 -3.9750 -0.1165 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7996 -0.6571 0.4395 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0411 1.3481 -0.3859 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1416 2.5204 -0.7212 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2815 1.9824 -0.5381 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2141 2.9002 -1.0015 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0091 3.5173 -0.1048 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6313 4.8895 -0.1269 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3152 5.5873 -1.1228 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7748 5.7748 -0.7427 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1638 4.6251 0.1803 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4823 3.3929 -0.4204 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9795 2.2376 0.1449 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5248 4.4677 0.2746 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9492 7.0025 -0.1444 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4187 3.5254 0.1833 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5818 0.7268 0.7440 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9117 -4.1719 -3.7546 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6717 1.2775 5.3284 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6528 0.1967 3.1295 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9857 -1.1676 1.1498 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0038 0.1205 1.7191 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6604 1.4851 3.6375 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2132 -4.1988 -0.8419 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6436 -6.5007 -1.9763 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9738 -5.8542 -4.0643 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2875 0.6556 -1.8212 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5972 0.9065 -2.3720 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8558 -1.4486 -0.5718 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5921 -1.5287 -2.2513 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6563 -2.9153 -0.7948 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3589 -0.2748 0.8015 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8337 -0.3959 2.9924 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5814 -0.6951 3.0442 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4206 -2.0739 3.2553 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4038 -2.3703 1.5504 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6788 -2.5620 -1.1180 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8636 -1.2853 -1.8759 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4172 -4.0889 -1.8341 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5531 -4.3962 -0.0813 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8597 -0.1103 1.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0649 1.7535 -0.2951 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3531 2.7823 -1.7665 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4017 1.9433 0.5456 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8889 3.2381 0.9549 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1992 5.1358 -2.1262 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8569 6.5950 -1.1628 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3810 5.6839 -1.6482 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7343 4.8137 1.1635 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6716 3.3325 -1.5106 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8286 2.3549 0.6391 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9073 4.7977 1.1347 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7255 6.8827 0.8241 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0851 3.2783 0.8482 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0381 -0.0974 0.9817 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5516 -5.0523 -4.0989 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 5 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 12 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 31 34 1 0 30 35 1 0 23 36 1 0 36 37 1 0 37 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 45 46 1 0 44 47 1 0 43 48 1 0 37 49 1 0 36 50 1 0 15 51 1 0 7 2 1 0 19 8 2 0 38 21 1 0 45 40 1 0 16 10 1 0 32 26 1 0 1 52 1 0 3 53 1 0 4 54 1 0 6 55 1 0 7 56 1 0 11 57 1 0 13 58 1 0 14 59 1 0 21 60 1 6 23 61 1 6 24 62 1 0 24 63 1 0 26 64 1 6 28 65 1 6 29 66 1 0 29 67 1 0 29 68 1 0 30 69 1 1 31 70 1 6 32 71 1 6 33 72 1 0 34 73 1 0 35 74 1 0 36 75 1 1 37 76 1 6 38 77 1 1 40 78 1 1 42 79 1 0 42 80 1 0 43 81 1 6 44 82 1 1 45 83 1 6 46 84 1 0 47 85 1 0 48 86 1 0 49 87 1 0 50 88 1 0 51 89 1 0 M END

Standard InCHIKey	LLPRITPJQPQXIR-PELFOGQRSA-N
Standard InCHI	InChI=1S/C32H38O19/c1-10-19(37)23(41)26(44)30(47-10)46-9-17-21(39)24(42)29(51-31-25(43)20(38)15(36)8-45-31)32(49-17)50-28-22(40)18-14(35)6-13(34)7-16(18)48-27(28)11-2-4-12(33)5-3-11/h2-7,10,15,17,19-21,23-26,29-39,41-44H,8-9H2,1H3/t10-,15-,17+,19-,20+,21-,23+,24-,25-,26+,29+,30+,31+,32-/m0/s1
SMILES	Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@@H]([C@@H]([C@H]1O[C@H]1OC[C@@H]([C@H]([C@@H]1O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	726.2	Volume:	656.612 ? Van der Waals volume.
Dense:	1.106	LogP:	0.95 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.391 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.377 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	36.0
TPSA:	308.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.111	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.27	Fsp³:	0.531
MCE-18:	148.102 ? 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:	0.623	Fluc inhibitor:	0.284 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.623 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.528 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.228	Promiscuous compounds:	0.562

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.749	MDCK Permeability:	-4.966
Pgp-inhibitor:	0.0	Pgp-substrate:	0.994
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):	0.049
20% Bioavailability (F20%):	0.109	30% Bioavailability (F30%):	0.968
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.005
Plasma Protein Binding (PPB):	81.078%	Volume Distribution (VD):	-0.105
Fu:	17.156% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.696
BSEP inhibitor:	0.125

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:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.038 ? 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):

0.748

Half-life (T1/2):

4.947

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.197
Human Hepatotoxicity (H-HT):	0.354	Drug-induced Liver Injury (DILI):	0.834
AMES Toxicity:	0.73	Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.11	Skin Sensitization:	0.993
Carcinogencity:	0.052	Eye Corrosion:	0.0
Eye Irritation:	0.626	Respiratory Toxicity:	0.024
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.923
Hematotoxicity:	0.054	Drug-induced Nephrotoxicity:	0.264
Genotoxicity:	0.827	RPMI-8226 Immunitoxicity:	0.158
A549 Cytotoxicity:	0.532	Hek293 Cytotoxicity:	0.748
BCF:	0.432 ? 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:	2.929 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.497 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.667 ? 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
NPO33513	hydrangeae dulcis folium	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11549443]
NPO33513	hydrangeae dulcis folium	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9871657]
NPO33513	hydrangeae dulcis folium	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]

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	4

Activity Type	# Activity
Organism	4

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
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	58.9	ng ml-1	DOI[10.6019/CHEMBL1201861]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	68.7	ng ml-1	DOI[10.6019/CHEMBL1201861]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	54.2	ng ml-1	PMID[17190454]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	37.6	ng ml-1	PMID[15620268]

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 NPC476470 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	20540
0.1-0.2	25407
0.2-0.3	3107
0.3-0.4	410
0.4-0.5	169
0.5-0.6	108
0.6-0.7	54
0.7-0.8	1
0.8-0.85	0
0.85-0.9	3
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC221342
0.9286	High Similarity	NPC12013
0.9286	High Similarity	NPC11432
0.9286	High Similarity	NPC477613
0.8864	High Similarity	NPC292929
0.8764	High Similarity	NPC602448
0.8523	High Similarity	NPC122467
0.7979	Intermediate Similarity	NPC89052
0.7935	Intermediate Similarity	NPC89127
0.7921	Intermediate Similarity	NPC192539
0.7917	Intermediate Similarity	NPC303694
0.7907	Intermediate Similarity	NPC476215
0.7865	Intermediate Similarity	NPC304741
0.7753	Intermediate Similarity	NPC173582
0.7753	Intermediate Similarity	NPC265885
0.7753	Intermediate Similarity	NPC181465
0.7753	Intermediate Similarity	NPC215710
0.7753	Intermediate Similarity	NPC473438
0.7753	Intermediate Similarity	NPC253788
0.764	Intermediate Similarity	NPC471079
0.7634	Intermediate Similarity	NPC142142
0.7556	Intermediate Similarity	NPC163242
0.7556	Intermediate Similarity	NPC272068
0.7449	Intermediate Similarity	NPC173837
0.7353	Intermediate Similarity	NPC480445
0.7222	Intermediate Similarity	NPC95866
0.7222	Intermediate Similarity	NPC473554
0.7204	Intermediate Similarity	NPC255157
0.7204	Intermediate Similarity	NPC259896
0.7115	Intermediate Similarity	NPC162394
0.7097	Intermediate Similarity	NPC203259
0.7097	Intermediate Similarity	NPC33054
0.7097	Intermediate Similarity	NPC176740
0.7097	Intermediate Similarity	NPC471725
0.7097	Intermediate Similarity	NPC134532
0.7097	Intermediate Similarity	NPC602582
0.703	Intermediate Similarity	NPC25523
0.6989	Remote Similarity	NPC470405
0.6989	Remote Similarity	NPC67326
0.6972	Remote Similarity	NPC487499
0.6923	Remote Similarity	NPC170052
0.6923	Remote Similarity	NPC135846
0.6915	Remote Similarity	NPC155877
0.6887	Remote Similarity	NPC480444
0.6875	Remote Similarity	NPC487502
0.6837	Remote Similarity	NPC76831
0.6762	Remote Similarity	NPC488734
0.6762	Remote Similarity	NPC488735
0.6762	Remote Similarity	NPC488739
0.6762	Remote Similarity	NPC488732
0.6762	Remote Similarity	NPC488738
0.6733	Remote Similarity	NPC203145
0.6667	Remote Similarity	NPC216496
0.6667	Remote Similarity	NPC476472
0.6667	Remote Similarity	NPC294815
0.6667	Remote Similarity	NPC16194
0.6633	Remote Similarity	NPC473327
0.6632	Remote Similarity	NPC39834
0.6607	Remote Similarity	NPC275977
0.6602	Remote Similarity	NPC219043
0.6591	Remote Similarity	NPC111929
0.6591	Remote Similarity	NPC320283
0.6591	Remote Similarity	NPC41121
0.6514	Remote Similarity	NPC488737
0.65	Remote Similarity	NPC220173
0.6496	Remote Similarity	NPC487500
0.6455	Remote Similarity	NPC480443
0.6441	Remote Similarity	NPC487501
0.6437	Remote Similarity	NPC54802
0.6437	Remote Similarity	NPC197304
0.6392	Remote Similarity	NPC65563
0.6392	Remote Similarity	NPC470949
0.6381	Remote Similarity	NPC480441
0.6346	Remote Similarity	NPC189564
0.633	Remote Similarity	NPC488740
0.633	Remote Similarity	NPC488736
0.633	Remote Similarity	NPC488733
0.6327	Remote Similarity	NPC473571
0.6327	Remote Similarity	NPC110941
0.6327	Remote Similarity	NPC186816
0.6316	Remote Similarity	NPC254855
0.6316	Remote Similarity	NPC94610
0.6286	Remote Similarity	NPC48984
0.6263	Remote Similarity	NPC240306
0.6224	Remote Similarity	NPC156869
0.6216	Remote Similarity	NPC209550
0.6174	Remote Similarity	NPC231787
0.617	Remote Similarity	NPC224530
0.6162	Remote Similarity	NPC470444
0.6078	Remote Similarity	NPC603079
0.6058	Remote Similarity	NPC218161
0.598	Remote Similarity	NPC32641
0.598	Remote Similarity	NPC256188
0.5978	Remote Similarity	NPC127546
0.5978	Remote Similarity	NPC57625
0.5978	Remote Similarity	NPC173637
0.5978	Remote Similarity	NPC317489
0.5978	Remote Similarity	NPC223424
0.5978	Remote Similarity	NPC600591
0.5966	Remote Similarity	NPC249560
0.5965	Remote Similarity	NPC480442
0.5913	Remote Similarity	NPC25946
0.5893	Remote Similarity	NPC474522
0.5876	Remote Similarity	NPC276377
0.5859	Remote Similarity	NPC187379
0.5833	Remote Similarity	NPC292019
0.5833	Remote Similarity	NPC202908
0.5833	Remote Similarity	NPC259957
0.5825	Remote Similarity	NPC35119
0.5824	Remote Similarity	NPC276222
0.5824	Remote Similarity	NPC274618
0.5824	Remote Similarity	NPC118284
0.5824	Remote Similarity	NPC608147
0.5816	Remote Similarity	NPC116864
0.5816	Remote Similarity	NPC244776
0.5806	Remote Similarity	NPC77672
0.5806	Remote Similarity	NPC133671
0.5806	Remote Similarity	NPC135391
0.5806	Remote Similarity	NPC78263
0.5806	Remote Similarity	NPC250069
0.5798	Remote Similarity	NPC30011
0.5798	Remote Similarity	NPC72554
0.5789	Remote Similarity	NPC241781
0.5784	Remote Similarity	NPC126784
0.5784	Remote Similarity	NPC241423
0.5784	Remote Similarity	NPC488074
0.5743	Remote Similarity	NPC605592
0.5729	Remote Similarity	NPC48093
0.5714	Remote Similarity	NPC33083
0.57	Remote Similarity	NPC139320
0.5686	Remote Similarity	NPC129264
0.5652	Remote Similarity	NPC288084
0.5631	Remote Similarity	NPC470125
0.5619	Remote Similarity	NPC97119
0.5614	Remote Similarity	NPC156785
0.5612	Remote Similarity	NPC223747
0.561	Remote Similarity	NPC97817
0.5567	Remote Similarity	NPC159579
0.5567	Remote Similarity	NPC219904
0.5566	Remote Similarity	NPC85751
0.5566	Remote Similarity	NPC471669
0.5566	Remote Similarity	NPC19240
0.5534	Remote Similarity	NPC35167
0.5532	Remote Similarity	NPC135599
0.5532	Remote Similarity	NPC73855
0.5532	Remote Similarity	NPC113968
0.5532	Remote Similarity	NPC328940
0.5532	Remote Similarity	NPC277174
0.5532	Remote Similarity	NPC606877
0.5526	Remote Similarity	NPC298666
0.5524	Remote Similarity	NPC270448
0.5481	Remote Similarity	NPC61904
0.5481	Remote Similarity	NPC153755
0.5474	Remote Similarity	NPC104677
0.5462	Remote Similarity	NPC21359
0.5462	Remote Similarity	NPC460984
0.5455	Remote Similarity	NPC488075
0.5429	Remote Similarity	NPC470443
0.5421	Remote Similarity	NPC470447
0.5417	Remote Similarity	NPC265530
0.5413	Remote Similarity	NPC214621
0.5413	Remote Similarity	NPC34267
0.5413	Remote Similarity	NPC14187
0.5408	Remote Similarity	NPC129217
0.5361	Remote Similarity	NPC46420
0.5333	Remote Similarity	NPC296018
0.5312	Remote Similarity	NPC249281
0.5294	Remote Similarity	NPC473682
0.5278	Remote Similarity	NPC473073
0.5258	Remote Similarity	NPC145038
0.5258	Remote Similarity	NPC56077
0.5258	Remote Similarity	NPC281131
0.5258	Remote Similarity	NPC64305
0.5258	Remote Similarity	NPC253662
0.5258	Remote Similarity	NPC179950
0.5258	Remote Similarity	NPC88789
0.5258	Remote Similarity	NPC491374
0.5253	Remote Similarity	NPC175107
0.5243	Remote Similarity	NPC258044
0.5243	Remote Similarity	NPC217387
0.5243	Remote Similarity	NPC609888
0.5238	Remote Similarity	NPC144097
0.5229	Remote Similarity	NPC470449
0.5225	Remote Similarity	NPC11468
0.52	Remote Similarity	NPC85707
0.5192	Remote Similarity	NPC44931
0.5192	Remote Similarity	NPC471748
0.5185	Remote Similarity	NPC221288
0.5185	Remote Similarity	NPC194836
0.5185	Remote Similarity	NPC91493
0.5185	Remote Similarity	NPC605081
0.5182	Remote Similarity	NPC223426
0.5152	Remote Similarity	NPC472459
0.5143	Remote Similarity	NPC150164
0.5138	Remote Similarity	NPC473071
0.5104	Remote Similarity	NPC67037
0.5104	Remote Similarity	NPC255615
0.51	Remote Similarity	NPC60735
0.51	Remote Similarity	NPC26230

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476470 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5714
0.1-0.2	3386
0.2-0.3	42
0.3-0.4	3
0.4-0.5	2
0.5-0.6	2
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
0.7097	Intermediate Similarity	NPD6797	Phase 2
0.5566	Remote Similarity	NPD7251	Phase 2
0.5225	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