NPASS Compound

Natural Product: NPC114505

Natural Product ID	NPC114505
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(+)-Dihydrodehydrodiconiferyl Alcohol-9-O-Beta-D-Glucopyranoside
IUPAC Name	(2R,3R,4S,5S,6R)-2-[[(2S,3R)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL466931
PubChem CID	44577121
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran 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 71 74 0 0 0 0 0 0 0 0999 V2000 -2.7028 5.5826 0.2067 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5112 5.0458 -1.0872 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 3.8876 -1.2996 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1702 3.2265 -0.2486 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4133 2.0687 -0.4383 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2874 1.6297 -1.7214 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8766 2.2871 -2.8100 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6138 3.4223 -2.5858 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2269 4.1204 -3.6479 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1736 1.4422 0.7493 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4819 -0.0222 0.6409 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4486 -0.4979 1.6725 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6599 0.1394 1.5875 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3453 -0.0521 0.4052 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8199 1.1803 -0.2768 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9981 0.8516 -1.1698 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9548 -0.5710 -1.6944 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7912 -1.5490 -0.5367 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0997 -2.2657 -0.2837 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9970 -3.1514 0.7814 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4884 -0.8547 0.6391 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9868 -0.7540 -2.6674 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1934 0.9921 -0.4560 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8513 1.8997 -0.9531 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8868 -0.5865 0.9571 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4631 -1.8233 0.7126 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7699 -2.1025 1.1122 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3266 -3.4386 0.8220 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0201 -3.4842 -0.5320 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5405 -4.9028 -0.6989 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4193 -5.1734 0.3233 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4891 -1.1062 1.7667 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9363 0.1270 2.0191 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6352 0.3453 1.5986 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8870 1.4888 1.7416 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6687 1.0914 2.6666 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9749 0.9503 3.1182 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0308 4.7081 0.8422 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7978 5.9907 0.6536 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5255 6.2978 0.2378 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2886 3.5970 0.7419 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3059 0.7227 -1.9045 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7361 1.8857 -3.7909 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0771 5.1407 -3.6312 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0491 2.0154 1.1212 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7169 -0.3971 -0.3514 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6438 -1.5798 1.4532 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9845 -0.4266 2.6772 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7165 -0.6940 -0.2681 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1967 1.8725 0.5341 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0243 1.5323 -2.0205 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9390 -0.7804 -2.1545 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0003 -2.2896 -0.7080 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3691 -2.8692 -1.1950 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9287 -1.5315 -0.1588 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9030 -3.3092 1.1758 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3923 -1.5272 -2.4858 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3390 1.9316 -0.1873 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0464 1.9577 -1.9077 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8659 -2.5550 0.2055 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4962 -4.1766 0.7728 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0254 -3.8026 1.5934 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8475 -2.7613 -0.5144 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2661 -3.2654 -1.3250 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6486 -5.5717 -0.5915 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9974 -4.9932 -1.7011 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1727 -5.9776 0.8478 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5027 -1.3796 2.0553 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0353 0.1062 3.8054 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3270 1.9063 3.5504 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6277 0.7803 2.2151 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 8 9 1 0 5 10 1 0 10 11 1 0 11 12 1 0 12 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 18 21 1 0 17 22 1 0 16 23 1 0 15 24 1 0 11 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 27 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 33 36 1 0 36 37 1 0 8 3 1 0 35 10 1 0 21 14 1 0 34 25 1 0 1 38 1 0 1 39 1 0 1 40 1 0 4 41 1 0 6 42 1 0 7 43 1 0 9 44 1 0 10 45 1 1 11 46 1 6 12 47 1 0 12 48 1 0 14 49 1 6 15 50 1 1 16 51 1 6 17 52 1 6 18 53 1 6 19 54 1 0 19 55 1 0 20 56 1 0 22 57 1 0 23 58 1 0 24 59 1 0 26 60 1 0 28 61 1 0 28 62 1 0 29 63 1 0 29 64 1 0 30 65 1 0 30 66 1 0 31 67 1 0 32 68 1 0 37 69 1 0 37 70 1 0 37 71 1 0 M END

Standard InCHIKey	VTKHRLZMWODHJA-KUCLMONLSA-N
Standard InCHI	InChI=1S/C26H34O11/c1-33-18-10-14(5-6-17(18)29)24-16(12-35-26-23(32)22(31)21(30)20(11-28)36-26)15-8-13(4-3-7-27)9-19(34-2)25(15)37-24/h5-6,8-10,16,20-24,26-32H,3-4,7,11-12H2,1-2H3/t16-,20+,21+,22-,23+,24+,26+/m0/s1
SMILES	COc1cc(ccc1O)[C@@H]1[C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)c2cc(CCCO)cc(c2O1)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	522.21	Volume:	504.9 ? Van der Waals volume.
Dense:	1.034	LogP:	1.201 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.732 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.186 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	22.0
TPSA:	167.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.255	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.331	Fsp³:	0.538
MCE-18:	87.1 ? 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:	0.51	Fluc inhibitor:	0.119 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.027 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.572 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.053	Promiscuous compounds:	0.069

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.79	MDCK Permeability:	-5.131
Pgp-inhibitor:	0.024	Pgp-substrate:	0.714
PAMPA:	0.306 ? 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):	0.492
20% Bioavailability (F20%):	0.254	30% Bioavailability (F30%):	0.97
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	0.416
Plasma Protein Binding (PPB):	69.47%	Volume Distribution (VD):	-0.394
Fu:	29.09% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.168
BSEP inhibitor:	0.365

ADMET: Metabolism

CYP1A2-inhibitor:	0.609	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.995	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.951	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.004	CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.269	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.003 ? 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):

2.879

Half-life (T1/2):

2.723

ADMET: Toxicity

hERG Blockers:	0.062	hERG Blockers (10um):	0.122
Human Hepatotoxicity (H-HT):	0.726	Drug-induced Liver Injury (DILI):	0.386
AMES Toxicity:	0.679	Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.032	Skin Sensitization:	0.99
Carcinogencity:	0.148	Eye Corrosion:	0.0
Eye Irritation:	0.365	Respiratory Toxicity:	0.053
Drug-induced Neurotoxicity:	0.056	Ototoxicity:	0.973
Hematotoxicity:	0.355	Drug-induced Nephrotoxicity:	0.816
Genotoxicity:	0.026	RPMI-8226 Immunitoxicity:	0.123
A549 Cytotoxicity:	0.685	Hek293 Cytotoxicity:	0.423
BCF:	0.495 ? 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:	2.953 ? 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:	3.634 ? 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
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14600382]
NPO33006	neoalsomitra integrifoliola	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18396904]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20476749]
NPO32535	dracocephalum ruyschiana	Species	Lamiaceae	Eukaryota	aerial parts	Mongolian	n.a.	PMID[23356964]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23713285]
NPO32734	disporum viridescens	Species	Colchicaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24246008]
NPO32734	disporum viridescens	Species	Colchicaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25467159]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[26296476]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26305406]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[29116780]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32807141]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38821245]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	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	1
IC50	5
Activity	1

Activity Type	# Activity
Cell line	5
Others	1
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
NPT76	Cell line	C6	Rattus norvegicus	Activity	=	140.04	%	PMID[22934600]
NPT147	Cell line	SK-MEL-2	Homo sapiens	IC50	>	10000.0	nM	PMID[12502331]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[19015349]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	Open TG-GATES in vivo data: Hematology
NPT148	Cell line	HCT-15	Homo sapiens	IC50	>	10000.0	nM	PubChem BioAssay data set
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	31.1	%	PMID[18396904]
NPT1	Others	Radical scavenging activity	n.a.	IC50	=	284000.0	nM	PMID[12182864]

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 NPC114505 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	17778
0.1-0.2	26876
0.2-0.3	4348
0.3-0.4	725
0.4-0.5	106
0.5-0.6	9
0.6-0.7	4
0.7-0.8	0
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC213074
0.8816	High Similarity	NPC15956
0.8072	Intermediate Similarity	NPC479449
0.8052	Intermediate Similarity	NPC193473
0.8052	Intermediate Similarity	NPC600128
0.7791	Intermediate Similarity	NPC98624
0.75	Intermediate Similarity	NPC472710
0.75	Intermediate Similarity	NPC472709
0.7439	Intermediate Similarity	NPC224674
0.7439	Intermediate Similarity	NPC64475
0.6053	Remote Similarity	NPC29799
0.6053	Remote Similarity	NPC263367
0.6053	Remote Similarity	NPC54743
0.6047	Remote Similarity	NPC478701
0.5747	Remote Similarity	NPC217635
0.5581	Remote Similarity	NPC199539
0.55	Remote Similarity	NPC316539
0.5435	Remote Similarity	NPC302610
0.5385	Remote Similarity	NPC115203
0.5309	Remote Similarity	NPC278961
0.5309	Remote Similarity	NPC113680
0.5055	Remote Similarity	NPC79429
0.5053	Remote Similarity	NPC125495

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC114505 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4789
0.1-0.2	4236
0.2-0.3	118
0.3-0.4	7
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