NPASS Compound

Natural Product: NPC470416

Natural Product ID	NPC470416
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-(6-E-Feruloyl)-Beta-D-Glucopyranoside
IUPAC Name	[(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]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2035003
PubChem CID	57408402
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003678] Flavonoid 3-O-p-coumaroyl 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 77 81 0 0 0 0 0 0 0 0999 V2000 9.0589 3.0979 -2.2157 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5062 1.8652 -1.6987 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6171 1.0372 -1.0345 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0790 -0.1664 -0.5366 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1723 -0.9730 0.1210 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8619 -0.5831 0.2690 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3815 0.6154 -0.2212 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2992 1.4149 -0.8781 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9988 1.0119 -0.0560 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5011 2.1416 -0.5058 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0829 2.4581 -0.2897 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5749 3.5298 -0.7066 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2404 1.5867 0.3853 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8693 1.8541 0.6149 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2871 0.6826 1.3791 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9685 0.4621 2.6935 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3677 -0.7000 3.3963 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8908 -1.2565 2.8236 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5665 -0.4806 1.7816 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0661 0.8433 1.6665 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0019 -0.3884 1.8771 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7780 -0.4476 0.7244 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3201 -1.5988 0.2757 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0291 -1.4954 -0.8599 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2166 -0.3911 -1.5222 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6903 0.8113 -1.1088 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9511 0.7779 0.0469 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4384 1.8316 0.4897 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8967 1.9882 -1.8250 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6398 2.0096 -2.9860 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1707 0.8075 -3.4066 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9654 -0.3541 -2.6973 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9246 0.8375 -4.5875 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8280 3.1997 -3.6784 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9409 4.0341 -3.3823 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3337 3.1611 -1.3459 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2129 -2.9270 0.8945 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7755 -3.1336 2.1430 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6589 -4.4467 2.6351 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9772 -5.5523 1.8899 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4275 -5.3213 0.6066 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5464 -4.0498 0.1109 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8580 -6.8478 2.3862 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6296 -2.5924 2.4276 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3564 -1.7095 3.4105 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3451 0.3744 2.5420 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4097 -0.5520 -0.6920 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9109 3.6701 -2.6385 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2852 2.8776 -2.9770 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5935 3.6754 -1.3703 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4669 -1.9197 0.5311 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1759 -1.2405 0.7908 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0244 2.3718 -1.2991 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3407 0.3281 0.4726 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0912 2.8619 -1.0354 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3702 1.8296 -0.3944 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7026 2.8090 1.1112 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4366 -0.2481 0.7709 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7766 1.3940 3.3035 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2369 -0.4461 4.4799 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6022 -1.3705 3.6955 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3655 -0.9034 0.7789 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3862 -1.2857 -3.0394 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4160 1.0756 -5.4284 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6852 3.9437 -4.1900 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4238 3.6688 -2.4401 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6312 5.0802 -3.1928 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7940 3.7901 -0.7222 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5362 -2.3134 2.7954 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3062 -4.5964 3.6367 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6830 -6.2029 0.0087 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9029 -3.8918 -0.8991 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7693 -7.6486 1.7772 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0081 -3.0333 3.0476 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9668 -1.6166 4.1801 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8016 1.1733 2.8416 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0863 -0.2984 0.0141 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 2 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 2 3 10 11 1 0 11 12 2 0 11 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 22 23 2 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 26 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 30 34 1 0 34 35 1 0 29 36 1 0 23 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 40 43 1 0 18 44 1 0 17 45 1 0 16 46 1 0 4 47 1 0 8 3 1 0 20 15 1 0 27 22 1 0 32 25 1 0 42 37 1 0 1 48 1 0 1 49 1 0 1 50 1 0 5 51 1 0 6 52 1 0 8 53 1 0 9 54 1 0 10 55 1 0 14 56 1 0 14 57 1 0 15 58 1 0 16 59 1 0 17 60 1 0 18 61 1 0 19 62 1 0 32 63 1 0 33 64 1 0 35 65 1 0 35 66 1 0 35 67 1 0 36 68 1 0 38 69 1 0 39 70 1 0 41 71 1 0 42 72 1 0 43 73 1 0 44 74 1 0 45 75 1 0 46 76 1 0 47 77 1 0 M END

Standard InCHIKey	GULOTKMXYIEWNB-HTCFYHAASA-N
Standard InCHI	InChI=1S/C32H30O15/c1-42-19-11-14(3-9-17(19)34)4-10-22(36)44-13-21-24(37)27(40)28(41)32(46-21)47-31-26(39)23-20(12-18(35)30(43-2)25(23)38)45-29(31)15-5-7-16(33)8-6-15/h3-12,21,24,27-28,32-35,37-38,40-41H,13H2,1-2H3/b10-4+/t21-,24-,27+,28-,32+/m1/s1
SMILES	COC1=C(C=CC(=C1)C=CC(=O)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

Calculated Properties

Physi-Chem Properties

Molecular Weight:	654.16	Volume:	616.825 ? Van der Waals volume.
Dense:	1.061	LogP:	1.458 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.714 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.22 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	32.0
TPSA:	235.04 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.101	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.321	Fsp³:	0.25
MCE-18:	110.5 ? 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:	0.709	Fluc inhibitor:	0.402 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.95 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.996 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.038	Promiscuous compounds:	0.676

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.115	MDCK Permeability:	-5.26
Pgp-inhibitor:	0.002	Pgp-substrate:	0.154
PAMPA:	0.976 ? 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):	0.313
20% Bioavailability (F20%):	0.771	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.596
Plasma Protein Binding (PPB):	84.079%	Volume Distribution (VD):	-0.135
Fu:	12.552% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.915
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.53
BSEP inhibitor:	0.802

ADMET: Metabolism

CYP1A2-inhibitor:	0.014	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.023	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.026	CYP2D6-substrate:	0.821
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.279
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.911 ? 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):

2.298

Half-life (T1/2):

2.457

ADMET: Toxicity

hERG Blockers:	0.085	hERG Blockers (10um):	0.621
Human Hepatotoxicity (H-HT):	0.405	Drug-induced Liver Injury (DILI):	0.614
AMES Toxicity:	0.702	Rat Oral Acute Toxicity:	0.281
Maximum Recommended Daily Dose:	0.813	Skin Sensitization:	0.954
Carcinogencity:	0.237	Eye Corrosion:	0.0
Eye Irritation:	0.118	Respiratory Toxicity:	0.126
Drug-induced Neurotoxicity:	0.14	Ototoxicity:	0.752
Hematotoxicity:	0.015	Drug-induced Nephrotoxicity:	0.112
Genotoxicity:	0.622	RPMI-8226 Immunitoxicity:	0.124
A549 Cytotoxicity:	0.576	Hek293 Cytotoxicity:	0.938
BCF:	0.68 ? 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:	3.423 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.693 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.139 ? 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	=	0.984	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 NPC470416 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	16735
0.1-0.2	28328
0.2-0.3	3627
0.3-0.4	744
0.4-0.5	284
0.5-0.6	94
0.6-0.7	30
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9101	High Similarity	NPC36138
0.7604	Intermediate Similarity	NPC85751
0.7604	Intermediate Similarity	NPC19240
0.7426	Intermediate Similarity	NPC217520
0.7374	Intermediate Similarity	NPC214621
0.7374	Intermediate Similarity	NPC34267
0.7273	Intermediate Similarity	NPC470450
0.7264	Intermediate Similarity	NPC488079
0.7264	Intermediate Similarity	NPC488078
0.7115	Intermediate Similarity	NPC139571
0.71	Intermediate Similarity	NPC223426
0.699	Remote Similarity	NPC480796
0.699	Remote Similarity	NPC477895
0.6907	Remote Similarity	NPC473571
0.6907	Remote Similarity	NPC110941
0.6863	Remote Similarity	NPC81042
0.6847	Remote Similarity	NPC25946
0.6827	Remote Similarity	NPC472993
0.6822	Remote Similarity	NPC474093
0.6822	Remote Similarity	NPC104910
0.6733	Remote Similarity	NPC470447
0.6667	Remote Similarity	NPC470449
0.6538	Remote Similarity	NPC470455
0.6452	Remote Similarity	NPC488080
0.6452	Remote Similarity	NPC169977
0.6348	Remote Similarity	NPC21359
0.6348	Remote Similarity	NPC460984
0.6337	Remote Similarity	NPC488074
0.6195	Remote Similarity	NPC470720
0.6176	Remote Similarity	NPC470125
0.6176	Remote Similarity	NPC488073
0.6176	Remote Similarity	NPC126784
0.6176	Remote Similarity	NPC241423
0.6176	Remote Similarity	NPC153755
0.6095	Remote Similarity	NPC80068
0.6075	Remote Similarity	NPC96605
0.6075	Remote Similarity	NPC280642
0.6038	Remote Similarity	NPC470445
0.6019	Remote Similarity	NPC599948
0.6	Remote Similarity	NPC270675
0.6	Remote Similarity	NPC195685
0.5981	Remote Similarity	NPC470446
0.5981	Remote Similarity	NPC218161
0.5966	Remote Similarity	NPC473554
0.5965	Remote Similarity	NPC470717
0.5943	Remote Similarity	NPC477629
0.5922	Remote Similarity	NPC129264
0.5918	Remote Similarity	NPC101026
0.5918	Remote Similarity	NPC488077
0.5905	Remote Similarity	NPC476620
0.5877	Remote Similarity	NPC470713
0.5876	Remote Similarity	NPC471405
0.584	Remote Similarity	NPC475179
0.5818	Remote Similarity	NPC470451
0.5773	Remote Similarity	NPC305811
0.5763	Remote Similarity	NPC480472
0.5743	Remote Similarity	NPC116864
0.5743	Remote Similarity	NPC244776
0.5727	Remote Similarity	NPC121703
0.5714	Remote Similarity	NPC42773
0.5714	Remote Similarity	NPC45522
0.5688	Remote Similarity	NPC472994
0.5636	Remote Similarity	NPC603856
0.5631	Remote Similarity	NPC471079
0.5631	Remote Similarity	NPC609888
0.5607	Remote Similarity	NPC270448
0.5607	Remote Similarity	NPC104883
0.5607	Remote Similarity	NPC488679
0.5577	Remote Similarity	NPC173582
0.5577	Remote Similarity	NPC265885
0.5577	Remote Similarity	NPC181465
0.5577	Remote Similarity	NPC215710
0.5577	Remote Similarity	NPC473438
0.5577	Remote Similarity	NPC253788
0.5537	Remote Similarity	NPC480470
0.5524	Remote Similarity	NPC65563
0.5524	Remote Similarity	NPC470949
0.5517	Remote Similarity	NPC295625
0.5505	Remote Similarity	NPC476472
0.5505	Remote Similarity	NPC294815
0.5505	Remote Similarity	NPC16194
0.5469	Remote Similarity	NPC487501
0.5455	Remote Similarity	NPC291296
0.5455	Remote Similarity	NPC10205
0.5446	Remote Similarity	NPC476869
0.5321	Remote Similarity	NPC473327
0.53	Remote Similarity	NPC24043
0.5294	Remote Similarity	NPC470719
0.5294	Remote Similarity	NPC474522
0.5288	Remote Similarity	NPC476865
0.5238	Remote Similarity	NPC479767
0.5207	Remote Similarity	NPC241781
0.5185	Remote Similarity	NPC470444
0.5185	Remote Similarity	NPC186816
0.5182	Remote Similarity	NPC37668
0.5172	Remote Similarity	NPC470712
0.5172	Remote Similarity	NPC164704
0.5167	Remote Similarity	NPC156785
0.5155	Remote Similarity	NPC291153
0.5152	Remote Similarity	NPC111929
0.5152	Remote Similarity	NPC320283
0.5152	Remote Similarity	NPC41121
0.5149	Remote Similarity	NPC46420
0.5143	Remote Similarity	NPC172807
0.514	Remote Similarity	NPC11411
0.514	Remote Similarity	NPC67326
0.514	Remote Similarity	NPC300262
0.5138	Remote Similarity	NPC296018
0.5135	Remote Similarity	NPC205824
0.51	Remote Similarity	NPC77672
0.51	Remote Similarity	NPC133671
0.51	Remote Similarity	NPC135391
0.51	Remote Similarity	NPC78263
0.51	Remote Similarity	NPC250069
0.5096	Remote Similarity	NPC223747
0.5096	Remote Similarity	NPC488082
0.5096	Remote Similarity	NPC476868
0.5093	Remote Similarity	NPC203259
0.5093	Remote Similarity	NPC133984
0.5093	Remote Similarity	NPC33054
0.5093	Remote Similarity	NPC176740
0.5093	Remote Similarity	NPC471725
0.5093	Remote Similarity	NPC134532
0.5093	Remote Similarity	NPC156869
0.5093	Remote Similarity	NPC602582
0.5088	Remote Similarity	NPC478277
0.5088	Remote Similarity	NPC478276
0.5088	Remote Similarity	NPC478275
0.5088	Remote Similarity	NPC92815
0.5085	Remote Similarity	NPC470718
0.5049	Remote Similarity	NPC175107
0.5048	Remote Similarity	NPC203050
0.5048	Remote Similarity	NPC225434
0.5042	Remote Similarity	NPC484988
0.5041	Remote Similarity	NPC162394

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470416 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4074
0.1-0.2	4997
0.2-0.3	66
0.3-0.4	9
0.4-0.5	3
0.5-0.6	1
0.6-0.7	0
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
0.5093	Remote Similarity	NPD6797	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