NPASS Compound

Natural Product: NPC520396

Natural Product ID	NPC520396
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	7-O-Methylrutin
IUPAC Name	2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{R},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 [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 76 80 0 0 0 0 0 0 0 0999 V2000 5.4076 4.2022 -5.5979 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1319 4.6390 -5.1524 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4583 3.9519 -4.1732 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2237 4.3801 -3.7551 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5667 3.6941 -2.7896 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3011 4.0675 -2.3094 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1367 2.5598 -2.2216 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4646 1.8863 -1.2547 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3179 2.2633 -0.8562 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0623 0.7103 -0.6653 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3569 0.1490 0.2452 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8793 -0.1940 1.4180 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1438 -1.3423 1.4200 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4809 -1.8048 2.4982 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9195 -2.2899 2.1595 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6511 -1.2544 1.6356 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9264 -1.7138 1.2911 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0448 -1.5497 -0.0610 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2626 -1.2479 -0.5813 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1280 -2.4572 -0.8622 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0694 -0.2107 0.1160 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4417 0.8404 -0.7410 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2886 0.3146 1.3022 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0836 1.1821 2.0445 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9122 -0.9181 2.1134 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0757 -1.6152 2.4075 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5344 -0.9722 3.7123 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2239 -1.5450 4.7693 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1981 0.4596 3.5117 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0668 1.3217 4.1937 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0214 0.8980 2.0747 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6551 2.1311 2.0458 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3036 0.3270 -1.1277 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0109 -0.8316 -0.6238 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3730 -0.9365 -0.9479 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1580 -1.9877 -0.5638 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6373 -3.0365 0.1903 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4378 -4.1019 0.5797 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3176 -2.9593 0.5185 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7660 -3.9871 1.2700 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5269 -1.8725 0.1116 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9069 1.0455 -2.0875 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3785 2.0951 -2.6144 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0143 2.8358 -3.6100 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0853 4.0859 -4.7521 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2815 3.2507 -6.2007 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7887 4.9422 -6.3099 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7520 5.2643 -4.1852 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4932 3.7228 -2.8351 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7206 -0.2503 2.1784 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0255 -2.7845 2.7904 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8792 -3.1057 1.4034 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4001 -2.7057 3.0617 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9901 -2.7969 1.5318 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0513 -0.8290 -1.6279 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7674 -2.6948 0.0097 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8546 -2.2212 -1.6919 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5493 -3.3261 -1.2051 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0321 -0.6545 0.4563 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1174 1.3634 -0.2351 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3885 0.8143 0.9023 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4939 1.8709 2.4241 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4917 -0.6006 3.0882 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0042 -2.5752 2.2673 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5896 -0.9993 4.1218 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0984 -2.4719 4.8330 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8128 0.6387 4.0040 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5924 0.7301 4.7998 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0006 0.9449 1.5825 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4327 2.5832 2.9119 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8193 -0.1229 -1.5405 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2007 -2.0576 -0.8238 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0347 -4.0166 1.4100 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2933 -3.7124 2.1322 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4996 -1.8894 0.3580 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9919 2.4772 -3.9219 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 5 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 1 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 19 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 14 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 10 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 37 39 1 0 39 40 1 0 39 41 2 0 33 42 1 0 42 43 1 0 43 44 2 0 44 3 1 0 43 7 1 0 31 12 1 0 41 34 1 0 25 17 1 0 1 45 1 0 1 46 1 0 1 47 1 0 4 48 1 0 6 49 1 0 12 50 1 1 14 51 1 1 15 52 1 0 15 53 1 0 17 54 1 6 19 55 1 6 20 56 1 0 20 57 1 0 20 58 1 0 21 59 1 1 22 60 1 0 23 61 1 6 24 62 1 0 25 63 1 1 26 64 1 0 27 65 1 1 28 66 1 0 29 67 1 1 30 68 1 0 31 69 1 6 32 70 1 0 35 71 1 0 36 72 1 0 38 73 1 0 40 74 1 0 41 75 1 0 44 76 1 0 M END

Standard InCHIKey	LVRWOUXRNRBDNV-GEBJFKNCSA-N
Standard InCHI	InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(41-9)40-8-16-19(33)22(36)24(38)28(43-16)44-26-20(34)17-14(31)6-11(39-2)7-15(17)42-25(26)10-3-4-12(29)13(30)5-10/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9-,16+,18-,19+,21+,22-,23+,24+,27+,28-/m0/s1
SMILES	COC1=CC(O)=C2C(=O)C(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)=C(C3=CC=C(O)C(O)=C3)OC2=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.17	Volume:	569.614 ? Van der Waals volume.
Dense:	1.096	LogP:	0.843 ? 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:	-2.367 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	258.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.137	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.751	Fsp³:	0.464
MCE-18:	122.073 ? 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:	0.623	Fluc inhibitor:	0.282 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.918 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.634 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.081	Promiscuous compounds:	0.492

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.332	MDCK Permeability:	-5.31
Pgp-inhibitor:	0.0	Pgp-substrate:	0.263
PAMPA:	0.993 ? 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):	0.566
20% Bioavailability (F20%):	0.182	30% Bioavailability (F30%):	0.984
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.026
Plasma Protein Binding (PPB):	82.019%	Volume Distribution (VD):	-0.111
Fu:	16.301% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.705
BSEP inhibitor:	0.011

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:	0.008
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.006
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.596
HLM stability:	0.633 ? 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):

1.97

Half-life (T1/2):

4.493

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.267
Human Hepatotoxicity (H-HT):	0.317	Drug-induced Liver Injury (DILI):	0.908
AMES Toxicity:	0.821	Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.033	Skin Sensitization:	0.991
Carcinogencity:	0.027	Eye Corrosion:	0.0
Eye Irritation:	0.194	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.97
Hematotoxicity:	0.04	Drug-induced Nephrotoxicity:	0.139
Genotoxicity:	0.443	RPMI-8226 Immunitoxicity:	0.067
A549 Cytotoxicity:	0.572	Hek293 Cytotoxicity:	0.27
BCF:	0.556 ? 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:	3.226 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.782 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.983 ? 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
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17243726]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8945	Grevillea robusta	Species	Proteaceae	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 NPC520396 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	19966
0.1-0.2	25904
0.2-0.3	2971
0.3-0.4	492
0.4-0.5	261
0.5-0.6	107
0.6-0.7	51
0.7-0.8	1
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8554	High Similarity	NPC186816
0.8353	Intermediate Similarity	NPC470443
0.8333	Intermediate Similarity	NPC271692
0.8023	Intermediate Similarity	NPC126784
0.8023	Intermediate Similarity	NPC241423
0.8	Intermediate Similarity	NPC203259
0.8	Intermediate Similarity	NPC33054
0.8	Intermediate Similarity	NPC176740
0.8	Intermediate Similarity	NPC471725
0.8	Intermediate Similarity	NPC134532
0.8	Intermediate Similarity	NPC602582
0.7882	Intermediate Similarity	NPC67105
0.7791	Intermediate Similarity	NPC210073
0.7667	Intermediate Similarity	NPC473073
0.766	Intermediate Similarity	NPC480441
0.7439	Intermediate Similarity	NPC46420
0.7363	Intermediate Similarity	NPC142142
0.7317	Intermediate Similarity	NPC158674
0.7294	Intermediate Similarity	NPC605784
0.7273	Intermediate Similarity	NPC173582
0.7273	Intermediate Similarity	NPC265885
0.7273	Intermediate Similarity	NPC181465
0.7273	Intermediate Similarity	NPC215710
0.7273	Intermediate Similarity	NPC473438
0.7273	Intermediate Similarity	NPC253788
0.7174	Intermediate Similarity	NPC486577
0.7111	Intermediate Similarity	NPC473571
0.7111	Intermediate Similarity	NPC110941
0.7097	Intermediate Similarity	NPC476472
0.7097	Intermediate Similarity	NPC294815
0.7097	Intermediate Similarity	NPC16194
0.7079	Intermediate Similarity	NPC44931
0.7079	Intermediate Similarity	NPC39834
0.7079	Intermediate Similarity	NPC227508
0.7065	Intermediate Similarity	NPC473327
0.7033	Intermediate Similarity	NPC488073
0.7	Intermediate Similarity	NPC22062
0.7	Intermediate Similarity	NPC65563
0.7	Intermediate Similarity	NPC473634
0.7	Intermediate Similarity	NPC470949
0.7	Intermediate Similarity	NPC138811
0.7	Intermediate Similarity	NPC156869
0.6988	Remote Similarity	NPC249281
0.6939	Remote Similarity	NPC25523
0.6905	Remote Similarity	NPC136042
0.6889	Remote Similarity	NPC67326
0.6882	Remote Similarity	NPC209296
0.6875	Remote Similarity	NPC14187
0.686	Remote Similarity	NPC611303
0.6848	Remote Similarity	NPC488074
0.6824	Remote Similarity	NPC84362
0.6824	Remote Similarity	NPC27640
0.6818	Remote Similarity	NPC276377
0.6598	Remote Similarity	NPC470446
0.6556	Remote Similarity	NPC116864
0.6556	Remote Similarity	NPC244776
0.6552	Remote Similarity	NPC59534
0.6526	Remote Similarity	NPC122467
0.6517	Remote Similarity	NPC116458
0.6517	Remote Similarity	NPC246943
0.65	Remote Similarity	NPC292019
0.65	Remote Similarity	NPC202908
0.6495	Remote Similarity	NPC470445
0.6465	Remote Similarity	NPC121703
0.6452	Remote Similarity	NPC150164
0.6437	Remote Similarity	NPC305811
0.6395	Remote Similarity	NPC127546
0.6395	Remote Similarity	NPC57625
0.6395	Remote Similarity	NPC173637
0.6395	Remote Similarity	NPC317489
0.6395	Remote Similarity	NPC238376
0.6395	Remote Similarity	NPC223424
0.6395	Remote Similarity	NPC600591
0.6392	Remote Similarity	NPC89127
0.6374	Remote Similarity	NPC265115
0.6316	Remote Similarity	NPC240306
0.625	Remote Similarity	NPC65711
0.6237	Remote Similarity	NPC471079
0.6207	Remote Similarity	NPC19709
0.6186	Remote Similarity	NPC32641
0.6186	Remote Similarity	NPC256188
0.6186	Remote Similarity	NPC72016
0.6186	Remote Similarity	NPC606657
0.617	Remote Similarity	NPC275454
0.6136	Remote Similarity	NPC297987
0.6129	Remote Similarity	NPC251417
0.6105	Remote Similarity	NPC303913
0.6082	Remote Similarity	NPC483414
0.6082	Remote Similarity	NPC483415
0.6064	Remote Similarity	NPC480466
0.6042	Remote Similarity	NPC204693
0.602	Remote Similarity	NPC483416
0.602	Remote Similarity	NPC35119
0.5963	Remote Similarity	NPC209550
0.5962	Remote Similarity	NPC303694
0.5938	Remote Similarity	NPC605592
0.5934	Remote Similarity	NPC488071
0.5922	Remote Similarity	NPC470451
0.5922	Remote Similarity	NPC189564
0.5918	Remote Similarity	NPC12013
0.5918	Remote Similarity	NPC11432
0.5918	Remote Similarity	NPC477613
0.5905	Remote Similarity	NPC277532
0.59	Remote Similarity	NPC471669
0.5859	Remote Similarity	NPC473623
0.5859	Remote Similarity	NPC229409
0.5843	Remote Similarity	NPC289667
0.5842	Remote Similarity	NPC101636
0.5842	Remote Similarity	NPC470449
0.5825	Remote Similarity	NPC89052
0.5825	Remote Similarity	NPC203145
0.5818	Remote Similarity	NPC241781
0.5816	Remote Similarity	NPC153755
0.58	Remote Similarity	NPC488089
0.5784	Remote Similarity	NPC135358
0.5769	Remote Similarity	NPC188871
0.5761	Remote Similarity	NPC175107
0.5743	Remote Similarity	NPC470447
0.573	Remote Similarity	NPC111929
0.573	Remote Similarity	NPC320283
0.573	Remote Similarity	NPC41121
0.5729	Remote Similarity	NPC187379
0.5714	Remote Similarity	NPC173837
0.5714	Remote Similarity	NPC349108
0.57	Remote Similarity	NPC37668
0.5686	Remote Similarity	NPC221342
0.5686	Remote Similarity	NPC476470
0.5684	Remote Similarity	NPC95866
0.5673	Remote Similarity	NPC11468
0.5667	Remote Similarity	NPC108831
0.5667	Remote Similarity	NPC182634
0.5657	Remote Similarity	NPC475366
0.5652	Remote Similarity	NPC42773
0.5652	Remote Similarity	NPC45522
0.5652	Remote Similarity	NPC599850
0.5638	Remote Similarity	NPC223747
0.5636	Remote Similarity	NPC156785
0.5636	Remote Similarity	NPC162394
0.5631	Remote Similarity	NPC223426
0.5631	Remote Similarity	NPC602448
0.5625	Remote Similarity	NPC254540
0.5604	Remote Similarity	NPC145038
0.5604	Remote Similarity	NPC56077
0.5604	Remote Similarity	NPC281131
0.5604	Remote Similarity	NPC253662
0.5604	Remote Similarity	NPC179950
0.5604	Remote Similarity	NPC277205
0.5604	Remote Similarity	NPC37919
0.5604	Remote Similarity	NPC88789
0.5604	Remote Similarity	NPC491374
0.5591	Remote Similarity	NPC219904
0.5579	Remote Similarity	NPC190003
0.5579	Remote Similarity	NPC355481
0.5577	Remote Similarity	NPC81042
0.5567	Remote Similarity	NPC609888
0.5556	Remote Similarity	NPC473043
0.5556	Remote Similarity	NPC135599
0.5556	Remote Similarity	NPC73855
0.5556	Remote Similarity	NPC331652
0.5556	Remote Similarity	NPC113968
0.5556	Remote Similarity	NPC328940
0.5556	Remote Similarity	NPC277174
0.5556	Remote Similarity	NPC606877
0.5536	Remote Similarity	NPC138990
0.5528	Remote Similarity	NPC482520
0.5528	Remote Similarity	NPC482519
0.55	Remote Similarity	NPC64425
0.5487	Remote Similarity	NPC175429
0.5474	Remote Similarity	NPC99957
0.5455	Remote Similarity	NPC473512
0.5455	Remote Similarity	NPC233994
0.5455	Remote Similarity	NPC155877
0.5446	Remote Similarity	NPC488078
0.5435	Remote Similarity	NPC265530
0.5435	Remote Similarity	NPC189142
0.5435	Remote Similarity	NPC77660
0.5429	Remote Similarity	NPC470455
0.54	Remote Similarity	NPC115674
0.5385	Remote Similarity	NPC298171
0.537	Remote Similarity	NPC473644
0.5354	Remote Similarity	NPC471748
0.5351	Remote Similarity	NPC192539
0.5347	Remote Similarity	NPC46202
0.5347	Remote Similarity	NPC64051
0.5333	Remote Similarity	NPC276222
0.5333	Remote Similarity	NPC274618
0.5333	Remote Similarity	NPC118284
0.5333	Remote Similarity	NPC608147
0.5321	Remote Similarity	NPC311850
0.531	Remote Similarity	NPC480444
0.5306	Remote Similarity	NPC480463
0.53	Remote Similarity	NPC479405
0.53	Remote Similarity	NPC129827
0.5299	Remote Similarity	NPC487499
0.5294	Remote Similarity	NPC211532
0.5294	Remote Similarity	NPC488364
0.5288	Remote Similarity	NPC473071
0.5288	Remote Similarity	NPC483412
0.528	Remote Similarity	NPC482521
0.5275	Remote Similarity	NPC67037

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC520396 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5245
0.1-0.2	3847
0.2-0.3	49
0.3-0.4	2
0.4-0.5	2
0.5-0.6	1
0.6-0.7	1
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8929	High Similarity	NPD7251	Phase 2
0.8	Intermediate Similarity	NPD6797	Phase 2
0.734	Intermediate Similarity	NPD7808	Phase 3
0.6882	Remote Similarity	NPD7054	Phase 4
0.5524	Remote Similarity	NPD7472	Pre-clinical

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