NPASS Compound

Natural Product: NPC294722

Natural Product ID	NPC294722
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cypellocarpa C
IUPAC Name	[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(5-hydroxy-2-methyl-4-oxochromen-7-yl)oxyoxan-2-yl]methyl (4R)-4-(2-hydroxypropan-2-yl)cyclohexene-1-carboxylate
Synonyms	Cypellocarpa C; Cypellocarpin C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL247486
PubChem CID	10625791
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

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 69 72 0 0 0 0 0 0 0 0999 V2000 10.1968 0.4312 0.9912 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0141 -0.2894 0.4147 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2434 -1.5102 -0.1992 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1799 -2.2051 -0.7425 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3457 -3.3177 -1.3090 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9152 -1.6402 -0.6465 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8078 -2.2737 -1.1642 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5572 -1.7019 -1.0621 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3528 -0.4679 -0.4372 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4797 0.1408 0.0704 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7528 -0.4215 -0.0229 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8096 0.1780 0.4684 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0784 0.0124 -0.3878 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6378 1.2207 0.1854 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0040 2.0449 -0.9085 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8889 2.9056 -0.4254 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1052 2.1639 0.3997 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4627 0.9118 0.9794 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0090 -0.3181 0.1993 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3772 -0.3166 -0.0606 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3677 -0.3096 0.8772 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0652 -0.3057 2.0933 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7779 -0.3063 0.4781 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1347 -0.3106 -0.7944 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5538 -0.3069 -1.1302 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4405 -1.1161 -0.2441 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0069 -1.1638 1.1875 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8230 -0.2977 1.4993 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8801 -0.6207 -0.3979 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8272 -1.4097 0.4827 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9854 0.8517 -0.1515 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2579 -0.8706 -1.7163 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8048 0.9112 1.2225 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 2.9788 1.4106 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2980 3.4961 -1.5618 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0139 2.9177 -1.3813 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0126 -3.5023 -1.7863 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0440 -0.2458 1.0881 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9164 0.9372 1.9423 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4167 1.2665 0.2750 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2360 -1.9345 -0.2642 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7064 -2.2130 -1.4727 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3819 1.0786 0.5548 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5044 1.7915 0.6326 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7603 1.4049 -1.7623 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2987 3.7491 0.1720 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9343 1.8502 -0.3010 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0278 0.7829 1.9932 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5144 -0.3842 -0.7857 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1982 -1.2439 0.8106 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3788 -0.3167 -1.5837 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9058 0.7652 -1.0761 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6792 -0.5910 -2.1949 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4451 -2.1570 -0.6299 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7854 -2.1975 1.5236 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8556 -0.8042 1.8087 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1120 0.7711 1.7071 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3845 -0.6642 2.4535 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8425 -1.4196 0.0449 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5142 -2.4681 0.5774 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8801 -0.8977 1.4691 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2039 1.2405 0.5320 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9129 1.3901 -1.1175 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9983 1.0451 0.3074 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7093 -1.7286 -1.8399 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3209 2.7189 2.3041 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8262 4.2571 -1.8783 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8317 2.3618 -1.4535 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6164 -4.3275 -1.3455 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 4 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 9 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 21 22 2 0 21 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 29 30 1 0 29 31 1 0 29 32 1 0 18 33 1 0 17 34 1 0 16 35 1 0 15 36 1 0 7 37 1 0 12 2 1 0 33 14 1 0 11 6 1 0 28 23 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 8 42 1 0 10 43 1 0 14 44 1 1 15 45 1 6 16 46 1 1 17 47 1 6 18 48 1 1 19 49 1 0 19 50 1 0 24 51 1 0 25 52 1 0 25 53 1 0 26 54 1 6 27 55 1 0 27 56 1 0 28 57 1 0 28 58 1 0 30 59 1 0 30 60 1 0 30 61 1 0 31 62 1 0 31 63 1 0 31 64 1 0 32 65 1 0 34 66 1 0 35 67 1 0 36 68 1 0 37 69 1 0 M END

Standard InCHIKey	OUBDJJFZUQGQLU-ZHFYLPRNSA-N
Standard InCHI	InChI=1S/C26H32O11/c1-12-8-16(27)20-17(28)9-15(10-18(20)35-12)36-25-23(31)22(30)21(29)19(37-25)11-34-24(32)13-4-6-14(7-5-13)26(2,3)33/h4,8-10,14,19,21-23,25,28-31,33H,5-7,11H2,1-3H3/t14-,19+,21+,22-,23+,25+/m0/s1
SMILES	Cc1cc(=O)c2c(cc(cc2o1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)C2=CC[C@@H](CC2)C(C)(C)O)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	520.19	Volume:	502.264 ? Van der Waals volume.
Dense:	1.036	LogP:	1.784 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.109 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.693 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	25.0
TPSA:	176.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.344	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.499	Fsp³:	0.538
MCE-18:	100.05 ? 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:	0.645	Fluc inhibitor:	0.198 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.233 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.58 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.026	Promiscuous compounds:	0.086

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.853	MDCK Permeability:	-5.103
Pgp-inhibitor:	0.234	Pgp-substrate:	0.062
PAMPA:	0.721 ? 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):	0.041
20% Bioavailability (F20%):	0.31	30% Bioavailability (F30%):	0.987
50% Bioavailability (F50%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013	MRP1:	0.377
Plasma Protein Binding (PPB):	82.866%	Volume Distribution (VD):	-0.378
Fu:	12.717% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.974

ADMET: Metabolism

CYP1A2-inhibitor:	0.185	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.09	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.912	CYP3A4-substrate:	0.03
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.22
HLM stability:	0.032 ? 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):

2.088

Half-life (T1/2):

2.571

ADMET: Toxicity

hERG Blockers:	0.036	hERG Blockers (10um):	0.199
Human Hepatotoxicity (H-HT):	0.532	Drug-induced Liver Injury (DILI):	0.974
AMES Toxicity:	0.888	Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.221	Skin Sensitization:	0.978
Carcinogencity:	0.52	Eye Corrosion:	0.0
Eye Irritation:	0.37	Respiratory Toxicity:	0.054
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.832
Hematotoxicity:	0.186	Drug-induced Nephrotoxicity:	0.534
Genotoxicity:	0.846	RPMI-8226 Immunitoxicity:	0.133
A549 Cytotoxicity:	0.316	Hek293 Cytotoxicity:	0.308
BCF:	0.587 ? 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:	3.317 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.882 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.127 ? 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
NPO20620	Eucalyptus cypellocarpa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000030]
NPO9838	Eucalyptus maideni	Species	Myrtaceae	Eukaryota	fresh leaves	n.a.	n.a.	PMID[19778089]
NPO9838	Eucalyptus maideni	Species	Myrtaceae	Eukaryota	fresh fruits	n.a.	n.a.	PMID[20092288]
NPO9838	Eucalyptus maideni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20620	Eucalyptus cypellocarpa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20620	Eucalyptus cypellocarpa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9838	Eucalyptus maideni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20620	Eucalyptus cypellocarpa	Species	Myrtaceae	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
Ratio	3
Activity	6
MNCC	1

Activity Type	# Activity
Cell line	5
Organism	1
Others	4

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
NPT492	Cell line	Caco-2	Homo sapiens	Ratio	=	2.74	n.a.	PubChem BioAssay data set
NPT492	Cell line	Caco-2	Homo sapiens	Ratio	=	1.8	n.a.	PubChem BioAssay data set
NPT492	Cell line	Caco-2	Homo sapiens	Ratio	=	1.81	n.a.	PMID[21105712]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[21741130]
NPT189	Cell line	Vero	Chlorocebus aethiops	MNCC	>	0.38	mM	PMID[19778089]
NPT2	Others	Unspecified	n.a.	Activity	=	19.5	%	DrugMatrix in vivo data: Pathology
NPT2	Others	Unspecified	n.a.	Activity	=	45.2	%	DrugMatrix in vivo data: Pathology
NPT2	Others	Unspecified	n.a.	Activity	=	78.6	%	PMID[1517742]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PMID[7911157]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	30.0	%	PMID[24359277]

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference
Homo sapiens	n.a.	Drug uptake	=	52.45	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	54.61	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	52.74	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	52.82	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	53.14	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	56.83	%	PMID[17118653]
Homo sapiens	n.a.	Papp	=	1.79	10^-6 cm/s	PMID[17118653]
Homo sapiens	n.a.	Papp	=	8.97	10^-7 cm/s	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	0.89	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	0.81	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	0.69	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	0.83	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	1.42	%	PMID[17118653]
Homo sapiens	n.a.	Papp	=	2.46	10^-6 cm/s	PMID[17118653]
Homo sapiens	n.a.	Papp	=	2.71	10^-6 cm/s	PMID[17118653]
Homo sapiens	n.a.	Papp	=	3.32	10^-6 cm/s	PMID[17118653]
Homo sapiens	n.a.	Papp	=	2.66	10^-6 cm/s	PMID[17118653]
Homo sapiens	n.a.	Papp	=	4.82	10^-6 cm/s	PMID[17118653]
Homo sapiens	n.a.	Papp	=	5.99	10^-6 cm/s	PMID[17118653]
Homo sapiens	n.a.	Papp	=	7.4	10^-6 cm/s	PMID[17118653]

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 NPC294722 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	6815
0.1-0.2	38306
0.2-0.3	4062
0.3-0.4	565
0.4-0.5	98
0.5-0.6	10
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	Natural Product ID
0.5862	Remote Similarity	NPC191154
0.5657	Remote Similarity	NPC475979
0.5306	Remote Similarity	NPC181616
0.5283	Remote Similarity	NPC270675
0.5283	Remote Similarity	NPC195685
0.5253	Remote Similarity	NPC99957
0.5248	Remote Similarity	NPC41009
0.5189	Remote Similarity	NPC473623
0.5138	Remote Similarity	NPC472994
0.5109	Remote Similarity	NPC134819

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC294722 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2975
0.1-0.2	6082
0.2-0.3	83
0.3-0.4	7
0.4-0.5	3
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