NPASS Compound

Natural Product: NPC35731

Natural Product ID	NPC35731
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Darendoside A
IUPAC Name	(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethoxy]-6-(hydroxymethyl)oxan-4-yl]oxy-6-methyloxane-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL462940
PubChem CID	21668724
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

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 65 67 0 0 0 0 0 0 0 0999 V2000 -7.1083 -0.3185 -0.6443 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7598 0.2339 -0.1988 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9420 0.8869 1.1276 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3552 0.0203 2.2322 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8804 -0.1418 1.8931 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6850 -0.5605 0.4587 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8736 -0.8246 -0.1932 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9129 0.3925 -0.1846 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6673 -0.1082 -0.6056 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6640 -0.0920 -2.0858 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3838 0.3339 -2.7175 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5179 0.5385 -4.1960 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9626 -0.6578 -4.7607 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0580 1.4833 -2.0655 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5860 0.9952 -0.8348 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5293 0.5629 0.0662 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0060 -0.1484 1.1348 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4308 1.9144 -0.2734 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7607 1.5616 -0.2239 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9972 0.3341 0.5953 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 -0.0107 0.6420 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2350 0.5214 1.6494 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5718 0.2130 1.7004 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1729 -0.6128 0.7769 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3926 -1.1387 -0.2253 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0518 -0.8384 -0.2889 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9622 -1.9710 -1.1689 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5118 -0.8795 0.8859 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3567 -0.3792 1.8757 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9825 -1.3630 -2.6202 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3597 -1.0643 2.7991 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0093 -1.1921 2.3207 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2308 2.0857 1.1481 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4500 -1.1025 0.0673 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9273 -0.8575 -1.6149 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8461 0.4731 -0.8090 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4972 1.0172 -0.9429 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0070 1.1242 1.3237 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4456 0.5862 3.1779 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4021 0.8498 2.0967 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0994 -1.5024 0.4744 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6441 -1.1929 -0.2869 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4714 0.5823 -2.4984 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3530 -0.5054 -2.5766 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1582 1.3974 -4.4645 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5049 0.7195 -4.5990 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1768 -1.2153 -5.0442 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1662 0.1085 -1.1419 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9331 1.5126 0.5289 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7010 -0.2510 1.8204 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4166 2.4061 0.0794 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0914 1.2991 -1.2723 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6408 0.5187 1.6450 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5126 -0.5527 0.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8114 1.1846 2.4122 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1504 0.6582 2.5198 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4163 -1.2500 -1.0821 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5594 -2.7377 -0.9662 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1513 0.6727 2.1099 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4049 -0.4385 1.4715 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3435 -0.9532 2.8213 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2363 -1.9610 -1.8669 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9209 -1.8712 2.7815 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6214 -1.2462 3.1104 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7179 2.7515 1.6712 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 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 11 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 25 27 1 0 24 28 1 0 28 29 1 0 10 30 1 0 5 31 1 0 4 32 1 0 3 33 1 0 7 2 1 0 16 9 1 0 26 21 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 6 3 38 1 1 4 39 1 1 5 40 1 6 6 41 1 1 9 42 1 6 10 43 1 1 11 44 1 6 12 45 1 0 12 46 1 0 13 47 1 0 15 48 1 6 16 49 1 1 17 50 1 0 19 51 1 0 19 52 1 0 20 53 1 0 20 54 1 0 22 55 1 0 23 56 1 0 26 57 1 0 27 58 1 0 29 59 1 0 29 60 1 0 29 61 1 0 30 62 1 0 31 63 1 0 32 64 1 0 33 65 1 0 M END

Standard InCHIKey	MMRYSDPTALIPSP-MGXJDOAZSA-N
Standard InCHI	InChI=1S/C21H32O12/c1-9-14(24)16(26)17(27)21(31-9)33-19-15(25)13(8-22)32-20(18(19)28)30-6-5-10-3-4-12(29-2)11(23)7-10/h3-4,7,9,13-28H,5-6,8H2,1-2H3/t9-,13+,14-,15+,16+,17+,18+,19-,20+,21-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1[C@@H]([C@@H](CO)O[C@H]([C@@H]1O)OCCc1ccc(c(c1)O)OC)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	476.19	Volume:	443.676 ? Van der Waals volume.
Dense:	1.073	LogP:	-1.071 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.043 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-0.999 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	18.0
TPSA:	187.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	7.0	Rings:	3.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.211	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.342	Fsp³:	0.714
MCE-18:	78.222 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.447	Fluc inhibitor:	0.082 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.136 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.113 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.13	Promiscuous compounds:	0.214

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.313	MDCK Permeability:	-5.192
Pgp-inhibitor:	0.003	Pgp-substrate:	0.979
PAMPA:	0.999 ? 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):	0.763
20% Bioavailability (F20%):	0.112	30% Bioavailability (F30%):	0.848
50% Bioavailability (F50%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.043
Plasma Protein Binding (PPB):	63.661%	Volume Distribution (VD):	-0.468
Fu:	36.475% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.988	BCRP inhibitor:	0.029
BSEP inhibitor:	0.008

ADMET: Metabolism

CYP1A2-inhibitor:	0.033	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.143	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.145	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.659	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.994
HLM stability:	0.419 ? 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):

1.759

Half-life (T1/2):

3.298

ADMET: Toxicity

hERG Blockers:	0.031	hERG Blockers (10um):	0.138
Human Hepatotoxicity (H-HT):	0.401	Drug-induced Liver Injury (DILI):	0.549
AMES Toxicity:	0.916	Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.005	Skin Sensitization:	0.997
Carcinogencity:	0.038	Eye Corrosion:	0.0
Eye Irritation:	0.061	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.988
Hematotoxicity:	0.375	Drug-induced Nephrotoxicity:	0.65
Genotoxicity:	0.02	RPMI-8226 Immunitoxicity:	0.155
A549 Cytotoxicity:	0.415	Hek293 Cytotoxicity:	0.3
BCF:	0.322 ? 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:	2.595 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.078 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.271 ? 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
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	flowering whole plant	n.a.	n.a.	PMID[10425119]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575955]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	stems	Yunnan Province, China	2004	PMID[17253844]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	purchased from Kyoungdong Oriental Herbal Market, Seoul, Korea	2006-APR	PMID[18052323]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	n.a.	n.a.	PMID[27310249]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	stem bark	Medicinal Plant Garden, College of Pharmacy, Ewha Womans University	2013-DEC	PMID[28787158]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599262]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748375]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18039	Herba dendrobii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18039	Herba dendrobii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17539	Ajuga decumbens	Species	Lamiaceae	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
Activity	4

Activity Type	# Activity
Cell line	4
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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[9748375]
NPT80	Cell line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[9748375]
NPT2	Others	Unspecified	n.a.	Inhibition	=	22.6	%	PMID[9748375]
NPT2	Others	Unspecified	n.a.	Inhibition	=	53.8	%	PMID[9748375]
NPT2	Others	Unspecified	n.a.	Inhibition	=	81.6	%	PMID[9748375]
NPT2	Others	Unspecified	n.a.	Inhibition	=	100.0	%	PMID[9748375]

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 NPC35731 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	13188
0.1-0.2	30364
0.2-0.3	5645
0.3-0.4	581
0.4-0.5	62
0.5-0.6	10
0.6-0.7	4
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
0.6667	Remote Similarity	NPC600370
0.64	Remote Similarity	NPC55608
0.6163	Remote Similarity	NPC252292
0.6023	Remote Similarity	NPC34927
0.5745	Remote Similarity	NPC470933
0.5595	Remote Similarity	NPC64141
0.5543	Remote Similarity	NPC259347
0.5441	Remote Similarity	NPC610709
0.5357	Remote Similarity	NPC235294
0.5326	Remote Similarity	NPC100998
0.5306	Remote Similarity	NPC306890
0.5233	Remote Similarity	NPC205195
0.5165	Remote Similarity	NPC34587
0.5067	Remote Similarity	NPC100558

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC35731 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3576
0.1-0.2	5361
0.2-0.3	206
0.3-0.4	6
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