NPASS Compound

Natural Product: NPC18699

Natural Product ID	NPC18699
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5,7-Dihydroxy-8-[2-(5-Hydroxy-7-Methoxy-4-Oxochromen-2-Yl)-5-Methoxyphenyl]-2-(4-Methoxyphenyl)Chromen-4-One
IUPAC Name	5,7-dihydroxy-8-[2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-5-methoxyphenyl]-2-(4-methoxyphenyl)chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL316312
PubChem CID	44327242
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

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 67 72 0 0 0 0 0 0 0 0999 V2000 -3.4052 -0.3194 5.1862 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2785 0.3762 3.9703 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0399 0.4977 3.3716 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9412 -0.0659 3.9780 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2860 0.0802 3.3405 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4199 0.7669 2.1339 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6796 1.3194 1.5462 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9096 1.1763 2.1798 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5246 2.0291 0.2877 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1505 3.2220 0.2071 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7142 3.7897 1.3538 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2529 3.8351 -1.0276 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3171 3.2435 -2.1341 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9946 2.0407 -2.0365 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1122 1.4113 -0.8316 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7445 0.2724 -0.6952 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3260 -0.3758 -1.6971 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2303 0.2252 -2.9282 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5716 1.4321 -3.1275 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4856 1.9750 -4.2396 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0125 -1.6442 -1.4594 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6232 -2.3375 -2.4615 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2721 -3.5517 -2.1906 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3218 -4.0873 -0.9306 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7019 -3.3853 0.0905 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0672 -2.1947 -0.1830 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9779 -5.2914 -0.7209 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0974 -5.9420 0.5195 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2315 3.8335 -3.3826 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7376 0.8756 1.5333 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7274 1.4482 2.2946 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9894 1.5773 1.7825 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9218 2.1073 2.4777 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2544 1.1326 0.5101 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2182 0.5632 -0.2131 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0227 0.4645 0.3307 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4832 0.1165 -1.4902 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7237 0.2076 -2.0819 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7491 0.7752 -1.3557 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5006 1.2270 -0.0765 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4997 1.8150 0.7174 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9278 -0.2648 -3.3826 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1946 -0.1802 -4.0100 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1112 -1.4053 5.0887 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7964 0.1433 6.0124 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4470 -0.3417 5.5533 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0507 -0.5977 4.9147 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1849 -0.3465 3.7790 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7467 1.6317 1.6724 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6573 4.1565 1.3409 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7922 4.7858 -1.0878 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6810 -0.2453 -3.7939 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6166 -1.9642 -3.4752 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7588 -4.1026 -2.9935 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7377 -3.8042 1.0887 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5821 -1.6411 0.6035 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2482 -5.2954 1.3803 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9846 -6.6341 0.4287 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1902 -6.5921 0.6353 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3703 3.3865 -4.0764 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5455 1.8073 3.3003 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6756 -0.3328 -2.0677 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7410 0.8660 -1.7833 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4297 2.8349 0.8519 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9040 -0.9456 -3.6071 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0550 -0.3653 -5.0962 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6878 0.8063 -3.8246 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 0 10 11 1 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 17 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 24 27 1 0 27 28 1 0 13 29 1 0 6 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 35 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 38 42 1 0 42 43 1 0 8 3 1 0 15 9 1 0 26 21 1 0 36 30 1 0 19 14 1 0 40 34 1 0 1 44 1 0 1 45 1 0 1 46 1 0 4 47 1 0 5 48 1 0 8 49 1 0 11 50 1 0 12 51 1 0 18 52 1 0 22 53 1 0 23 54 1 0 25 55 1 0 26 56 1 0 28 57 1 0 28 58 1 0 28 59 1 0 29 60 1 0 31 61 1 0 37 62 1 0 39 63 1 0 41 64 1 0 43 65 1 0 43 66 1 0 43 67 1 0 M END

Standard InCHIKey	LDDWBTHCKGZOCL-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C33H24O10/c1-39-17-6-4-16(5-7-17)27-14-26(38)32-24(36)13-23(35)30(33(32)43-27)21-10-18(40-2)8-9-20(21)28-15-25(37)31-22(34)11-19(41-3)12-29(31)42-28/h4-15,34-36H,1-3H3
SMILES	COc1ccc(c(c1)c1c(O)cc(c2c1oc(cc2=O)c1ccc(cc1)OC)O)c1cc(=O)c2c(o1)cc(cc2O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	580.14	Volume:	573.704 ? Van der Waals volume.
Dense:	1.011	LogP:	4.479 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.438 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.288 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	36.0
TPSA:	148.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.213	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.971	Fsp³:	0.091
MCE-18:	36.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.997	Fluc inhibitor:	0.418 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.874 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.997 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.331	Promiscuous compounds:	0.856

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.035	MDCK Permeability:	-4.776
Pgp-inhibitor:	0.844	Pgp-substrate:	0.528
PAMPA:	0.013 ? 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):	0.022
20% Bioavailability (F20%):	0.149	30% Bioavailability (F30%):	0.617
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.865
Plasma Protein Binding (PPB):	96.422%	Volume Distribution (VD):	-0.032
Fu:	2.467% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.986
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.993
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.979	CYP1A2-substrate:	0.444
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.996	CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.007
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.992 ? 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):

1.436

Half-life (T1/2):

1.571

ADMET: Toxicity

hERG Blockers:	0.163	hERG Blockers (10um):	0.462
Human Hepatotoxicity (H-HT):	0.467	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.868	Rat Oral Acute Toxicity:	0.561
Maximum Recommended Daily Dose:	0.969	Skin Sensitization:	0.076
Carcinogencity:	0.936	Eye Corrosion:	0.001
Eye Irritation:	0.952	Respiratory Toxicity:	0.952
Drug-induced Neurotoxicity:	0.015	Ototoxicity:	0.079
Hematotoxicity:	0.155	Drug-induced Nephrotoxicity:	0.111
Genotoxicity:	0.995	RPMI-8226 Immunitoxicity:	0.22
A549 Cytotoxicity:	0.575	Hek293 Cytotoxicity:	0.902
BCF:	1.363 ? 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:	4.5 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.325 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.855 ? 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
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.plantsci.2006.08.002]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0168-9452(01)00432-0]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	n.a.	n.a.	PMID[12444707]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	Yunnang Province, China	2000-OCT	PMID[21138310]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	xylem	n.a.	PMID[21138310]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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
ED50	7
Inhibition	7

Activity Type	# Activity
Cell line	12
Non-molecular	2

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
NPT1178	Cell line	KB 3-1	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[18345642]
NPT1178	Cell line	KB 3-1	Homo sapiens	Inhibition	=	9.0	%	PMID[7328598]
NPT81	Cell line	A549	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[19919065]
NPT81	Cell line	A549	Homo sapiens	Inhibition	=	58.0	%	PMID[19919065]
NPT83	Cell line	MCF7	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[15974608]
NPT83	Cell line	MCF7	Homo sapiens	Inhibition	=	22.0	%	PMID[26110443]
NPT147	Cell line	SK-MEL-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[18640837]
NPT147	Cell line	SK-MEL-2	Homo sapiens	Inhibition	=	9.0	%	PubChem BioAssay data set
NPT307	Cell line	HOS	Homo sapiens	ED50	>	20.0	ug ml-1	DOI[10.1007/s00044-011-9937-1]
NPT307	Cell line	HOS	Homo sapiens	Inhibition	=	25.0	%	DOI[10.1007/s00044-011-9937-1]
NPT1535	Cell line	U-87 MG	Homo sapiens	ED50	>	20.0	ug ml-1	DOI[10.1007/s00044-011-9937-1]
NPT1535	Cell line	U-87 MG	Homo sapiens	Inhibition	=	17.0	%	DOI[10.1007/s00044-011-9903-y]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[12217376]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	44.0	%	PMID[12217376]

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 NPC18699 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	31317
0.1-0.2	16018
0.2-0.3	1835
0.3-0.4	489
0.4-0.5	151
0.5-0.6	33
0.6-0.7	8
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
0.9	High Similarity	NPC55443
0.7534	Intermediate Similarity	NPC14606
0.7432	Intermediate Similarity	NPC121649
0.6923	Remote Similarity	NPC29353
0.6795	Remote Similarity	NPC265624
0.6623	Remote Similarity	NPC194593
0.6282	Remote Similarity	NPC158027
0.6234	Remote Similarity	NPC248739
0.6154	Remote Similarity	NPC150908
0.6076	Remote Similarity	NPC303485
0.6056	Remote Similarity	NPC195202
0.5942	Remote Similarity	NPC127447
0.5857	Remote Similarity	NPC231772
0.5857	Remote Similarity	NPC234133
0.5833	Remote Similarity	NPC223579
0.5714	Remote Similarity	NPC52611
0.5663	Remote Similarity	NPC601565
0.5634	Remote Similarity	NPC33265
0.5634	Remote Similarity	NPC48479
0.5616	Remote Similarity	NPC124784
0.561	Remote Similarity	NPC159707
0.561	Remote Similarity	NPC186227
0.5556	Remote Similarity	NPC108406
0.5556	Remote Similarity	NPC603508
0.5541	Remote Similarity	NPC137062
0.5488	Remote Similarity	NPC71061
0.5476	Remote Similarity	NPC205026
0.5443	Remote Similarity	NPC254351
0.5405	Remote Similarity	NPC177298
0.5366	Remote Similarity	NPC601984
0.5333	Remote Similarity	NPC610914
0.5294	Remote Similarity	NPC95090
0.5294	Remote Similarity	NPC27408
0.5227	Remote Similarity	NPC80188
0.5205	Remote Similarity	NPC57030
0.5205	Remote Similarity	NPC145379
0.5135	Remote Similarity	NPC603662
0.5119	Remote Similarity	NPC600396
0.5068	Remote Similarity	NPC262094
0.5068	Remote Similarity	NPC156222
0.5068	Remote Similarity	NPC600177
0.5067	Remote Similarity	NPC328119
0.5057	Remote Similarity	NPC181712
0.5056	Remote Similarity	NPC608742

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC18699 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6080
0.1-0.2	3015
0.2-0.3	46
0.3-0.4	7
0.4-0.5	2
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