NPASS Compound

Natural Product: NPC470449

Natural Product ID	NPC470449
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6-Methoxykaempferol-3-O-(4-O-Acetyl)-Alpha-L-Rhamnopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name	[(2S,3R,4S,5R,6R)-6-[[(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4,5-dihydroxy-2-methyloxan-3-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2037052
PubChem CID	57409960
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 81 85 0 0 0 0 0 0 0 0999 V2000 6.0403 1.4848 -0.3298 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2840 0.4565 0.4449 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2946 -0.4169 1.1778 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0111 -1.8541 0.7699 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5793 -2.1645 1.0694 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6586 -1.1523 0.3760 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4582 -0.3020 -0.3869 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8729 -0.5003 1.2917 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5256 -0.7030 1.2038 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9147 -0.2430 -0.0843 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9931 1.2727 -0.2127 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6819 1.5481 -1.6912 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4082 0.5955 -2.1318 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2257 0.0702 -0.9732 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4432 -0.5487 -0.0280 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1614 1.0039 -0.4681 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4944 0.6773 -0.4506 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0358 0.1600 0.6815 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3428 -0.1453 0.5910 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0607 0.0337 -0.4843 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5429 0.5594 -1.6452 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2099 0.8923 -1.6231 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7052 1.3747 -2.6609 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3262 0.7442 -2.7855 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6616 0.4054 -2.7976 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1879 -0.1223 -1.6381 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4093 -0.3021 -0.5159 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5341 -0.4646 -1.6489 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4517 0.5839 -3.9249 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1639 1.7878 -4.1657 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7242 1.2828 -3.9190 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4084 -0.0985 1.9472 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2034 0.3623 2.3746 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6548 0.0145 3.6191 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3177 -0.8213 4.4836 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5420 -1.3010 4.0741 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0676 -0.9535 2.8533 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7505 -1.1457 5.7038 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1027 -0.5046 -2.8322 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8331 1.1867 -2.3890 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2450 1.7469 0.1524 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2933 -3.4655 0.7292 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3145 -1.9743 -0.5860 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6199 -0.0298 0.8658 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4960 0.3732 1.8525 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0528 0.3789 3.0437 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8945 0.7838 1.5514 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4164 2.2556 -0.7965 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6666 1.0015 -1.0850 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7656 1.9511 0.3986 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6462 0.9531 1.2093 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1536 -0.3295 2.2743 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6945 -2.4829 1.3399 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4384 -2.0374 2.1681 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0563 -1.7603 -0.3293 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2237 -1.7625 1.3787 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0496 -0.1407 2.0590 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4460 -0.6906 -0.9176 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1941 1.6888 0.4289 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4331 2.6055 -1.8601 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0686 1.1445 -2.8119 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8440 -0.7714 -1.4234 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8537 -0.7170 0.3723 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9438 -1.1320 -2.2815 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1736 1.7321 -3.7035 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6258 2.6587 -3.7208 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2775 1.9984 -5.2453 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6715 2.2626 -4.1247 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6848 1.0359 1.7224 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7012 0.4310 3.8554 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0463 -1.9565 4.7704 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0435 -1.3795 2.6063 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0082 -1.9877 6.2258 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1271 -0.3773 -3.7985 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6137 1.2309 -3.3577 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7241 2.0477 -0.6669 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6346 -4.0546 1.4579 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7314 -2.6444 -1.0313 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3741 0.1032 0.8375 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9086 1.7995 1.0937 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5126 0.7926 2.4720 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 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 14 15 1 0 14 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 21 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 26 28 1 0 25 29 1 0 29 30 1 0 24 31 1 0 18 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 35 38 1 0 13 39 1 0 12 40 1 0 11 41 1 0 5 42 1 0 4 43 1 0 3 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 7 2 1 0 15 10 1 0 22 17 1 0 27 20 1 0 37 32 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 0 3 52 1 0 4 53 1 0 5 54 1 0 6 55 1 0 9 56 1 0 9 57 1 0 10 58 1 0 11 59 1 0 12 60 1 0 13 61 1 0 14 62 1 0 27 63 1 0 28 64 1 0 30 65 1 0 30 66 1 0 30 67 1 0 31 68 1 0 33 69 1 0 34 70 1 0 36 71 1 0 37 72 1 0 38 73 1 0 39 74 1 0 40 75 1 0 41 76 1 0 42 77 1 0 43 78 1 0 47 79 1 0 47 80 1 0 47 81 1 0 M END

Standard InCHIKey	GQGGGIGWHXSINI-GPTBGJQJSA-N
Standard InCHI	InChI=1S/C30H34O17/c1-10-25(44-11(2)31)22(38)24(40)29(43-10)42-9-16-18(34)21(37)23(39)30(46-16)47-28-20(36)17-15(8-14(33)27(41-3)19(17)35)45-26(28)12-4-6-13(32)7-5-12/h4-8,10,16,18,21-25,29-30,32-35,37-40H,9H2,1-3H3/t10-,16+,18+,21-,22-,23+,24+,25-,29+,30-/m0/s1
SMILES	CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=C(C3=O)C(=C(C(=C4)O)OC)O)C5=CC=C(C=C5)O)O)O)O)O)O)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	666.18	Volume:	610.359 ? Van der Waals volume.
Dense:	1.091	LogP:	0.435 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.042 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.3 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	31.0
TPSA:	264.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.137	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.879	Fsp³:	0.467
MCE-18:	124.364 ? 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:	0.166	Fluc inhibitor:	0.032 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.832 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.904 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.074	Promiscuous compounds:	0.171

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.168	MDCK Permeability:	-5.272
Pgp-inhibitor:	0.0	Pgp-substrate:	0.965
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):	0.585
20% Bioavailability (F20%):	0.146	30% Bioavailability (F30%):	0.942
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.939
Plasma Protein Binding (PPB):	80.387%	Volume Distribution (VD):	-0.082
Fu:	19.99% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.005
OATP1B3 inhibitor:	0.892	BCRP inhibitor:	0.352
BSEP inhibitor:	0.178

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.039	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.448 ? 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):

1.665

Half-life (T1/2):

2.983

ADMET: Toxicity

hERG Blockers:	0.033	hERG Blockers (10um):	0.427
Human Hepatotoxicity (H-HT):	0.387	Drug-induced Liver Injury (DILI):	0.795
AMES Toxicity:	0.688	Rat Oral Acute Toxicity:	0.388
Maximum Recommended Daily Dose:	0.507	Skin Sensitization:	0.228
Carcinogencity:	0.126	Eye Corrosion:	0.0
Eye Irritation:	0.025	Respiratory Toxicity:	0.028
Drug-induced Neurotoxicity:	0.164	Ototoxicity:	0.935
Hematotoxicity:	0.019	Drug-induced Nephrotoxicity:	0.021
Genotoxicity:	0.823	RPMI-8226 Immunitoxicity:	0.066
A549 Cytotoxicity:	0.148	Hek293 Cytotoxicity:	0.843
BCF:	0.391 ? 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:	2.971 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.734 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.8 ? 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
NPO33486	paepalanthus geniculatus	Species	Eriocaulaceae	Eukaryota	Flowers	Santana do Riacho, State Minas Gerais, Brazil	n.a.	PMID[22506638]
NPO33486	paepalanthus geniculatus	Species	Eriocaulaceae	Eukaryota	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	1

Activity Type	# Activity
Non-molecular	1

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	0.968	mM	PMID[22506638]

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 NPC470449 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	14065
0.1-0.2	31734
0.2-0.3	3160
0.3-0.4	476
0.4-0.5	281
0.5-0.6	88
0.6-0.7	30
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8977	High Similarity	NPC470446
0.8182	Intermediate Similarity	NPC473571
0.8182	Intermediate Similarity	NPC110941
0.7872	Intermediate Similarity	NPC470455
0.7742	Intermediate Similarity	NPC470447
0.7347	Intermediate Similarity	NPC470451
0.7312	Intermediate Similarity	NPC126784
0.7312	Intermediate Similarity	NPC241423
0.7128	Intermediate Similarity	NPC488073
0.7128	Intermediate Similarity	NPC488074
0.6939	Remote Similarity	NPC36138
0.6939	Remote Similarity	NPC470445
0.6869	Remote Similarity	NPC470450
0.6742	Remote Similarity	NPC488080
0.6742	Remote Similarity	NPC169977
0.6667	Remote Similarity	NPC470416
0.6632	Remote Similarity	NPC173582
0.6632	Remote Similarity	NPC265885
0.6632	Remote Similarity	NPC181465
0.6632	Remote Similarity	NPC215710
0.6632	Remote Similarity	NPC473438
0.6632	Remote Similarity	NPC253788
0.6562	Remote Similarity	NPC65563
0.6562	Remote Similarity	NPC470949
0.6413	Remote Similarity	NPC159579
0.6354	Remote Similarity	NPC471079
0.6196	Remote Similarity	NPC305811
0.6176	Remote Similarity	NPC476472
0.6176	Remote Similarity	NPC294815
0.6176	Remote Similarity	NPC16194
0.6162	Remote Similarity	NPC186816
0.6139	Remote Similarity	NPC473327
0.61	Remote Similarity	NPC153755
0.6061	Remote Similarity	NPC203259
0.6061	Remote Similarity	NPC33054
0.6061	Remote Similarity	NPC176740
0.6061	Remote Similarity	NPC471725
0.6061	Remote Similarity	NPC134532
0.6061	Remote Similarity	NPC602582
0.6038	Remote Similarity	NPC189564
0.5979	Remote Similarity	NPC116864
0.5979	Remote Similarity	NPC244776
0.5957	Remote Similarity	NPC42773
0.5957	Remote Similarity	NPC45522
0.5938	Remote Similarity	NPC209023
0.5922	Remote Similarity	NPC488089
0.59	Remote Similarity	NPC156869
0.5882	Remote Similarity	NPC483415
0.5865	Remote Similarity	NPC471669
0.5833	Remote Similarity	NPC101026
0.5833	Remote Similarity	NPC488077
0.58	Remote Similarity	NPC67326
0.5728	Remote Similarity	NPC75574
0.5728	Remote Similarity	NPC470443
0.5714	Remote Similarity	NPC85751
0.5714	Remote Similarity	NPC19240
0.57	Remote Similarity	NPC609888
0.5686	Remote Similarity	NPC129264
0.5686	Remote Similarity	NPC470444
0.5648	Remote Similarity	NPC121703
0.5648	Remote Similarity	NPC203145
0.5644	Remote Similarity	NPC39834
0.5566	Remote Similarity	NPC473073
0.5556	Remote Similarity	NPC214621
0.5556	Remote Similarity	NPC34267
0.5545	Remote Similarity	NPC292019
0.5545	Remote Similarity	NPC202908
0.5545	Remote Similarity	NPC139320
0.5532	Remote Similarity	NPC111929
0.5532	Remote Similarity	NPC320283
0.5532	Remote Similarity	NPC41121
0.5524	Remote Similarity	NPC270448
0.5524	Remote Similarity	NPC104883
0.5524	Remote Similarity	NPC488679
0.5521	Remote Similarity	NPC46420
0.5521	Remote Similarity	NPC24043
0.5481	Remote Similarity	NPC470125
0.5429	Remote Similarity	NPC12013
0.5429	Remote Similarity	NPC11432
0.5429	Remote Similarity	NPC477613
0.5408	Remote Similarity	NPC182121
0.5405	Remote Similarity	NPC173837
0.5357	Remote Similarity	NPC217520
0.5354	Remote Similarity	NPC85707
0.5347	Remote Similarity	NPC172807
0.5345	Remote Similarity	NPC474522
0.5327	Remote Similarity	NPC142142
0.5321	Remote Similarity	NPC223426
0.5312	Remote Similarity	NPC77672
0.5312	Remote Similarity	NPC133671
0.5312	Remote Similarity	NPC135391
0.5312	Remote Similarity	NPC78263
0.5312	Remote Similarity	NPC250069
0.5278	Remote Similarity	NPC483413
0.5278	Remote Similarity	NPC483412
0.5278	Remote Similarity	NPC89127
0.5268	Remote Similarity	NPC477895
0.5246	Remote Similarity	NPC231787
0.5238	Remote Similarity	NPC266960
0.5229	Remote Similarity	NPC221342
0.5229	Remote Similarity	NPC476470
0.52	Remote Similarity	NPC259957
0.5182	Remote Similarity	NPC602448
0.5161	Remote Similarity	NPC72554
0.5155	Remote Similarity	NPC249281
0.5149	Remote Similarity	NPC223747
0.5135	Remote Similarity	NPC81042
0.513	Remote Similarity	NPC139571
0.5126	Remote Similarity	NPC241781
0.5102	Remote Similarity	NPC265530
0.51	Remote Similarity	NPC175107
0.51	Remote Similarity	NPC219904
0.51	Remote Similarity	NPC129217
0.5098	Remote Similarity	NPC276377
0.5093	Remote Similarity	NPC483416
0.5093	Remote Similarity	NPC37668
0.5091	Remote Similarity	NPC292929
0.5091	Remote Similarity	NPC101636
0.5089	Remote Similarity	NPC89052
0.5088	Remote Similarity	NPC25523
0.5085	Remote Similarity	NPC156785
0.5053	Remote Similarity	NPC54802
0.5053	Remote Similarity	NPC197304
0.5051	Remote Similarity	NPC27640
0.5049	Remote Similarity	NPC477848
0.5048	Remote Similarity	NPC44931
0.5048	Remote Similarity	NPC471748
0.5047	Remote Similarity	NPC296018

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470449 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4607
0.1-0.2	4484
0.2-0.3	47
0.3-0.4	7
0.4-0.5	3
0.5-0.6	1
0.6-0.7	1
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
0.6061	Remote Similarity	NPD6797	Phase 2
0.5278	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