NPASS Compound

Natural Product: NPC569621

Natural Product ID	NPC569621
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-(4-hydroxy-3,5-dimethoxy-phenyl)-6,7-dimethoxy-5-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	2-(4-hydroxy-3,5-dimethoxy-phenyl)-6,7-dimethoxy-5-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-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] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid 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 86 90 0 0 0 0 0 0 0 0999 V2000 -8.4327 -2.7064 -1.4530 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6034 -2.5302 -0.0631 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6308 -1.8545 0.6767 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4807 -1.3407 0.0744 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5231 -0.6780 0.7941 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3351 -0.1389 0.1411 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3224 0.5057 0.8018 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2053 1.0021 0.1297 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2994 1.5921 0.7703 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0809 0.8592 -1.2305 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0179 1.3221 -1.9675 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0421 1.9674 -1.3472 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2479 1.3293 -0.9882 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5049 1.2268 0.3502 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8628 1.0949 0.6458 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9350 0.6252 2.0790 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1885 0.4407 2.5802 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9866 -0.4825 1.9641 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3273 -1.5582 2.7898 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8502 -2.5713 1.9816 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9774 -2.9124 0.8070 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2256 -2.2029 1.4335 C 0 0 2 0 0 0 0 0 0 0 0 0 8.1690 -3.0171 2.0235 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4792 -0.7548 1.7843 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8051 -0.6628 3.1138 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2696 0.1011 1.4218 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5439 1.3736 1.9206 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4548 2.4757 0.5598 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0941 3.1384 1.7475 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8675 3.1291 -0.6634 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7739 3.8895 -0.2593 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3642 2.1299 -1.6898 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3471 1.3062 -2.1731 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9514 1.1603 -3.3358 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1088 1.6184 -4.1242 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0678 2.9347 -4.6942 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0018 0.5042 -3.9583 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9346 0.3403 -5.3383 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0148 -0.3304 -5.9631 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0592 0.0430 -3.2132 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1532 0.1927 -1.8436 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1751 -0.2522 -1.1652 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6929 -0.5119 2.1440 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8221 -1.0038 2.8007 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0301 -0.8564 4.1599 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1042 -0.1890 4.9989 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7538 -1.6602 2.0348 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9164 -2.1835 2.6218 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4090 -1.7405 -1.9686 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5223 -3.3023 -1.6908 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3634 -3.2313 -1.8107 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3409 -1.4683 -0.9835 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3851 0.6356 1.8683 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2384 0.2623 -1.3750 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3657 0.3603 0.0163 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4037 1.3323 2.7683 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3937 -0.3577 2.2062 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4344 -0.9303 1.1151 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9258 -3.4872 2.6214 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2233 -3.9736 0.5271 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9034 -2.8990 1.0112 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2505 -2.3295 -0.1159 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2893 -2.3664 0.3369 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0483 -2.7891 1.5996 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3312 -0.4123 1.1589 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7244 -1.5426 3.5351 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2715 0.1807 0.3138 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7225 1.2494 2.8989 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5392 2.5062 0.4496 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7608 2.8159 2.4271 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5794 3.8475 -1.1423 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4670 3.5802 0.6432 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9505 2.7335 -2.5092 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1210 1.0560 -3.1188 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9846 3.0806 -5.0700 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1771 3.6495 -3.8514 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8025 3.0538 -5.4889 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9617 0.2638 -5.8457 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2260 -1.3210 -5.5191 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8600 -0.4525 -7.0508 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8936 -0.4780 -3.7027 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9989 -0.0027 2.7993 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2407 -0.8568 5.1394 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5900 0.1026 5.9704 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7617 0.7502 4.5347 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3377 -1.7227 3.4227 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 15 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 11 34 1 0 34 35 1 0 35 36 1 0 34 37 2 0 37 38 1 0 38 39 1 0 37 40 1 0 40 41 2 0 41 42 1 0 5 43 2 0 43 44 1 0 44 45 1 0 45 46 1 0 44 47 2 0 47 48 1 0 47 3 1 0 42 6 1 0 41 10 1 0 32 13 1 0 26 18 1 0 1 49 1 0 1 50 1 0 1 51 1 0 4 52 1 0 7 53 1 0 13 54 1 6 15 55 1 6 16 56 1 0 16 57 1 0 18 58 1 6 20 59 1 1 21 60 1 0 21 61 1 0 21 62 1 0 22 63 1 6 23 64 1 0 24 65 1 6 25 66 1 0 26 67 1 6 27 68 1 0 28 69 1 6 29 70 1 0 30 71 1 6 31 72 1 0 32 73 1 6 33 74 1 0 36 75 1 0 36 76 1 0 36 77 1 0 39 78 1 0 39 79 1 0 39 80 1 0 40 81 1 0 43 82 1 0 46 83 1 0 46 84 1 0 46 85 1 0 48 86 1 0 M END

Standard InCHIKey	OGSQJZZYZNAPHL-SOZFNCQKSA-N
Standard InCHI	InChI=1S/C31H38O17/c1-11-21(33)24(36)26(38)30(45-11)44-10-19-23(35)25(37)27(39)31(47-19)48-29-20-13(32)8-14(46-15(20)9-18(42-4)28(29)43-5)12-6-16(40-2)22(34)17(7-12)41-3/h6-9,11,19,21,23-27,30-31,33-39H,10H2,1-5H3/t11-,19+,21-,23-,24-,25-,26-,27+,30+,31-/m0/s1
SMILES	COC1=CC(C2=CC(=O)C3=C(O[C@@H]4O[C@H](CO[C@@H]5O[C@@H](C)[C@H](O)[C@H](O)[C@@H]5O)[C@H](O)[C@H](O)[C@H]4O)C(OC)=C(OC)C=C3O2)=CC(OC)=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	682.21	Volume:	630.292 ? Van der Waals volume.
Dense:	1.082	LogP:	0.662 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.057 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.199 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	30.0
TPSA:	245.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.139	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.837	Fsp³:	0.516
MCE-18:	123.319 ? 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:	0
Colloidal aggregators:	0.578	Fluc inhibitor:	0.089 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.759 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.602 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.032	Promiscuous compounds:	0.211

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.999	MDCK Permeability:	-5.405
Pgp-inhibitor:	0.0	Pgp-substrate:	0.77
PAMPA:	0.985 ? 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%):	0.885	30% Bioavailability (F30%):	0.926
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.98
Plasma Protein Binding (PPB):	85.856%	Volume Distribution (VD):	-0.169
Fu:	14.547% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.814
BSEP inhibitor:	0.036

ADMET: Metabolism

CYP1A2-inhibitor:	0.092	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.11	CYP2C19-substrate:	0.007
CYP2C9-inhibitor:	0.03	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.284
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.215
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.993
HLM stability:	0.763 ? 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):

1.496

Half-life (T1/2):

2.893

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.113
Human Hepatotoxicity (H-HT):	0.567	Drug-induced Liver Injury (DILI):	0.982
AMES Toxicity:	0.973	Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.057	Skin Sensitization:	1.0
Carcinogencity:	0.368	Eye Corrosion:	0.0
Eye Irritation:	0.209	Respiratory Toxicity:	0.167
Drug-induced Neurotoxicity:	0.087	Ototoxicity:	0.848
Hematotoxicity:	0.838	Drug-induced Nephrotoxicity:	0.773
Genotoxicity:	0.629	RPMI-8226 Immunitoxicity:	0.474
A549 Cytotoxicity:	0.965	Hek293 Cytotoxicity:	0.844
BCF:	0.361 ? 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:	3.112 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.302 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.646 ? 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
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	Flowers	Tantempango, Hidalgo, Mexico	2019-May	DOI[10.1007/s11130-020-00822-2]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16297615]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18543151]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24358188]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778246]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	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 NPC569621 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	19899
0.1-0.2	26182
0.2-0.3	2929
0.3-0.4	614
0.4-0.5	175
0.5-0.6	51
0.6-0.7	8
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
0.6667	Remote Similarity	NPC475366
0.6383	Remote Similarity	NPC204693
0.6277	Remote Similarity	NPC22062
0.6277	Remote Similarity	NPC473634
0.6277	Remote Similarity	NPC138811
0.6186	Remote Similarity	NPC209296
0.617	Remote Similarity	NPC15358
0.6	Remote Similarity	NPC44931
0.5938	Remote Similarity	NPC210073
0.5773	Remote Similarity	NPC473512
0.5773	Remote Similarity	NPC129827
0.5699	Remote Similarity	NPC606560
0.5657	Remote Similarity	NPC284277
0.5657	Remote Similarity	NPC475497
0.5612	Remote Similarity	NPC475155
0.56	Remote Similarity	NPC470443
0.5588	Remote Similarity	NPC476472
0.5588	Remote Similarity	NPC294815
0.5588	Remote Similarity	NPC16194
0.5567	Remote Similarity	NPC295613
0.5567	Remote Similarity	NPC473657
0.5556	Remote Similarity	NPC473571
0.5556	Remote Similarity	NPC110941
0.55	Remote Similarity	NPC126784
0.55	Remote Similarity	NPC241423
0.5484	Remote Similarity	NPC222936
0.5474	Remote Similarity	NPC99957
0.5392	Remote Similarity	NPC473327
0.534	Remote Similarity	NPC488089
0.5288	Remote Similarity	NPC473073
0.5248	Remote Similarity	NPC186816
0.5243	Remote Similarity	NPC473623
0.5243	Remote Similarity	NPC483707
0.5217	Remote Similarity	NPC114740
0.5208	Remote Similarity	NPC181616
0.5204	Remote Similarity	NPC172807
0.5204	Remote Similarity	NPC211594
0.52	Remote Similarity	NPC173582
0.52	Remote Similarity	NPC265885
0.52	Remote Similarity	NPC181465
0.52	Remote Similarity	NPC215710
0.52	Remote Similarity	NPC39834
0.52	Remote Similarity	NPC67105
0.52	Remote Similarity	NPC473438
0.52	Remote Similarity	NPC227508
0.52	Remote Similarity	NPC253788
0.5152	Remote Similarity	NPC254540
0.5149	Remote Similarity	NPC203259
0.5149	Remote Similarity	NPC65563
0.5149	Remote Similarity	NPC33054
0.5149	Remote Similarity	NPC470949
0.5149	Remote Similarity	NPC176740
0.5149	Remote Similarity	NPC471725
0.5149	Remote Similarity	NPC134532
0.5149	Remote Similarity	NPC602582
0.51	Remote Similarity	NPC187379
0.51	Remote Similarity	NPC609888
0.5093	Remote Similarity	NPC11468
0.5049	Remote Similarity	NPC46202

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC569621 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5045
0.1-0.2	4047
0.2-0.3	46
0.3-0.4	6
0.4-0.5	1
0.5-0.6	2
0.6-0.7	2
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
0.6465	Remote Similarity	NPD7472	Pre-clinical
0.6186	Remote Similarity	NPD7054	Phase 4
0.5149	Remote Similarity	NPD6797	Phase 2
0.5093	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