NPASS Compound

Natural Product: NPC469417

Natural Product ID	NPC469417
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Paeonidanin A
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1078412
PubChem CID	44253993
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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 82 0 0 0 0 0 0 0 0999 V2000 -0.6640 -4.2699 -1.4660 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7968 -3.2819 -1.2910 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8481 -3.4476 -2.3241 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6541 -2.1962 -2.3514 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8287 -2.2869 -2.6321 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9280 -0.9690 -2.0304 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4922 -1.1374 -2.5213 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2230 -1.8417 -1.2174 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3482 -1.1317 -0.6154 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0309 -2.1809 0.2051 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3519 -3.3796 -0.0354 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9025 -1.8349 1.5491 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0920 -1.6926 2.2191 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2414 0.2176 -0.0150 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5903 0.7423 0.0031 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8804 1.9983 0.5018 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9086 2.6913 0.9525 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2141 2.5587 0.5374 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4402 3.8175 1.0476 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7080 4.3876 1.0975 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7733 3.6561 0.6150 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5744 2.3736 0.0903 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2997 1.8584 0.0653 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0070 -1.9335 -0.7554 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8526 -0.9192 -0.5393 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2385 -0.9649 0.9352 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7737 0.3894 1.2966 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7013 0.7908 0.1675 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0967 -0.3771 -0.7075 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0214 -0.9812 -1.3312 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0230 0.1880 -1.7617 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1513 0.8253 -1.1974 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0853 0.2255 -0.4030 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9888 -0.9748 -0.1200 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2259 0.9882 0.1349 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4048 2.3286 -0.1346 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4733 3.0460 0.3686 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3961 2.4142 1.1662 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2365 1.0771 1.4477 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1670 0.3842 0.9366 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1142 1.7858 -0.6008 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4920 0.3388 2.4730 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1556 -1.3660 1.6690 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1508 -4.0012 -0.7823 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3045 -4.2344 -2.5078 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0982 -5.2771 -1.2321 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4441 -3.6564 -3.3418 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5239 -4.2837 -1.9999 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3887 -0.0160 -2.2456 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4718 -1.7664 -3.4271 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0102 -0.1626 -2.5629 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0953 -2.2457 -0.0314 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8374 -1.4169 3.2691 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6102 -2.6890 2.2221 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7547 -0.9302 1.8167 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9353 0.2320 1.0242 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7150 0.9117 -0.6977 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6376 4.4381 1.4413 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8685 5.3837 1.5039 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7666 4.0616 0.6363 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4410 1.8382 -0.2765 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1459 0.8732 -0.3376 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4919 0.1119 -0.7261 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0282 -1.7411 1.0432 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9640 1.1159 1.3532 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6357 1.2151 0.5869 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6749 -1.1195 -0.1236 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4400 1.0106 -2.2710 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3054 -0.5704 -2.5183 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6772 2.8246 -0.7631 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6054 4.0848 0.1555 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2555 2.9201 1.5917 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9628 0.5855 2.0736 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0475 -0.6678 1.1625 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5417 2.6624 -0.4849 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3382 -0.4905 2.9962 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1156 -0.9168 2.5416 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 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 9 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 8 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 28 41 1 0 27 42 1 0 26 43 1 0 8 2 1 0 11 2 1 0 9 6 1 0 23 18 1 0 30 25 1 0 40 35 1 0 1 44 1 0 1 45 1 0 1 46 1 0 3 47 1 0 3 48 1 0 6 49 1 0 7 50 1 0 7 51 1 0 10 52 1 0 13 53 1 0 13 54 1 0 13 55 1 0 14 56 1 0 14 57 1 0 19 58 1 0 20 59 1 0 21 60 1 0 22 61 1 0 23 62 1 0 25 63 1 0 26 64 1 0 27 65 1 0 28 66 1 0 29 67 1 0 31 68 1 0 31 69 1 0 36 70 1 0 37 71 1 0 38 72 1 0 39 73 1 0 40 74 1 0 41 75 1 0 42 76 1 0 43 77 1 0 M END

Standard InCHIKey	FHQISCVSTDQXSV-WNKDLFHOSA-N
Standard InCHI	InChI=1S/C31H34O12/c1-29-14-20(32)19-13-31(29,30(19,28(38-2)43-29)16-40-26(37)18-11-7-4-8-12-18)42-27-24(35)23(34)22(33)21(41-27)15-39-25(36)17-9-5-3-6-10-17/h3-12,19,21-24,27-28,33-35H,13-16H2,1-2H3/t19-,21-,22-,23+,24-,27+,28+,29+,30+,31-/m1/s1
SMILES	CC12CC(=O)C3CC1(C3(C(O2)OC)COC(=O)C4=CC=CC=C4)OC5C(C(C(C(O5)COC(=O)C6=CC=CC=C6)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	598.21	Volume:	575.148 ? Van der Waals volume.
Dense:	1.04	LogP:	1.839 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.134 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.31 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	32.0
TPSA:	167.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	3.0	Rings:	7.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.351	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.868	Fsp³:	0.516
MCE-18:	136.915 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.482	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.02 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.453 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.062	Promiscuous compounds:	0.0

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.798	MDCK Permeability:	-5.124
Pgp-inhibitor:	0.46	Pgp-substrate:	0.273
PAMPA:	0.817 ? 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):	0.005
20% Bioavailability (F20%):	0.006	30% Bioavailability (F30%):	0.075
50% Bioavailability (F50%):	0.71

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.318	MRP1:	0.991
Plasma Protein Binding (PPB):	76.308%	Volume Distribution (VD):	-0.75
Fu:	36.134% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.036
OATP1B3 inhibitor:	0.978	BCRP inhibitor:	0.002
BSEP inhibitor:	0.986

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.025
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	1.0 ? 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):

3.578

Half-life (T1/2):

1.184

ADMET: Toxicity

hERG Blockers:	0.155	hERG Blockers (10um):	0.732
Human Hepatotoxicity (H-HT):	0.05	Drug-induced Liver Injury (DILI):	0.491
AMES Toxicity:	0.403	Rat Oral Acute Toxicity:	0.147
Maximum Recommended Daily Dose:	0.446	Skin Sensitization:	0.237
Carcinogencity:	0.554	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.011
Drug-induced Neurotoxicity:	0.816	Ototoxicity:	0.808
Hematotoxicity:	0.005	Drug-induced Nephrotoxicity:	0.08
Genotoxicity:	0.19	RPMI-8226 Immunitoxicity:	0.1
A549 Cytotoxicity:	0.036	Hek293 Cytotoxicity:	0.75
BCF:	0.542 ? 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:	3.536 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.439 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.489 ? 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
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11339628]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17260795]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	Daejeon, Korea	2007-Jan	PMID[19670875]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	roots	n.a.	n.a.	PMID[19691309]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[20822014]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22547314]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	root bark	Bozhou, Anhui Province, China	2010-AUG	PMID[24377852]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	flower	n.a.	PMID[24504864]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	Flowers	LuoYang, HeNan, China	n.a.	PMID[24621197]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	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

Activity Type	# Activity
Inhibition	4
IC50	2

Activity Type	# Activity
Cell line	6

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
NPT848	Cell line	N9	Homo sapiens	Inhibition	=	86.6	%	PMID[20937542]
NPT848	Cell line	N9	Homo sapiens	Inhibition	=	74.9	%	PMID[18070958]
NPT848	Cell line	N9	Homo sapiens	Inhibition	=	59.1	%	PubChem BioAssay data set
NPT848	Cell line	N9	Homo sapiens	Inhibition	=	57.2	%	PMID[19748781]
NPT848	Cell line	N9	Homo sapiens	IC50	=	36200.0	nM	PMID[25014640]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[15217275]

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 NPC469417 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	10291
0.1-0.2	35537
0.2-0.3	3794
0.3-0.4	178
0.4-0.5	18
0.5-0.6	19
0.6-0.7	13
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9189	High Similarity	NPC469419
0.8831	High Similarity	NPC469418
0.8571	High Similarity	NPC469420
0.7532	Intermediate Similarity	NPC469448
0.7111	Intermediate Similarity	NPC469421
0.7037	Intermediate Similarity	NPC469422
0.6914	Remote Similarity	NPC34066
0.6914	Remote Similarity	NPC190862
0.6552	Remote Similarity	NPC469396
0.6552	Remote Similarity	NPC469458
0.6552	Remote Similarity	NPC149002
0.6463	Remote Similarity	NPC469399
0.6375	Remote Similarity	NPC478832
0.6344	Remote Similarity	NPC188217
0.6333	Remote Similarity	NPC260300
0.6222	Remote Similarity	NPC80360
0.6092	Remote Similarity	NPC88176
0.6049	Remote Similarity	NPC478831
0.6	Remote Similarity	NPC469398
0.593	Remote Similarity	NPC222102
0.5745	Remote Similarity	NPC148185
0.5698	Remote Similarity	NPC303429
0.5698	Remote Similarity	NPC56594
0.5638	Remote Similarity	NPC195114
0.5567	Remote Similarity	NPC478828
0.5545	Remote Similarity	NPC469397
0.54	Remote Similarity	NPC478829
0.5347	Remote Similarity	NPC478826
0.5347	Remote Similarity	NPC478827
0.5287	Remote Similarity	NPC133430
0.5281	Remote Similarity	NPC469477
0.5269	Remote Similarity	NPC469415
0.5217	Remote Similarity	NPC117943
0.5116	Remote Similarity	NPC478830
0.5104	Remote Similarity	NPC469438
0.5098	Remote Similarity	NPC477617
0.5067	Remote Similarity	NPC114096
0.5056	Remote Similarity	NPC469456

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC469417 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3220
0.1-0.2	5770
0.2-0.3	159
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
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
		NPD

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