NPASS Compound

Natural Product: NPC592710

Natural Product ID	NPC592710
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Nitensoside A
IUPAC Name	5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic 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 75 79 0 0 0 0 0 0 0 0999 V2000 3.9040 4.3157 0.3944 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7427 3.5645 0.1689 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8170 2.2001 0.0367 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0393 1.5794 0.1274 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1598 0.1933 -0.0015 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0255 -0.5278 -0.2206 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8100 0.0995 -0.3098 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6956 -0.6914 -0.5336 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6435 1.4709 -0.1883 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 2.0762 -0.2824 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4752 2.3075 0.8015 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6111 1.5212 0.7196 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6733 2.1168 0.0801 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6033 1.1409 -0.5998 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1634 0.2432 0.2926 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0208 -0.6621 -0.3072 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2654 -0.5051 0.2507 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1501 -1.5265 0.0213 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6836 -1.4967 -1.4192 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6615 -2.8963 0.3397 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5311 -3.5599 1.2064 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2742 -2.7723 0.9564 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7338 -4.0315 1.1848 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4416 -2.0426 -0.1084 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5779 -2.8095 -1.2737 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2387 3.2266 -0.8319 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3065 3.7332 -1.5452 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7693 4.3491 0.1044 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3429 5.4513 -0.6043 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7382 3.7568 1.0076 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0915 4.0040 2.3532 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1589 -1.9057 -0.3473 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1668 -2.6273 -0.5485 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4340 -2.4474 -0.2418 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5508 -1.6748 -0.0196 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9029 -2.2168 0.0958 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9506 -1.3538 0.3190 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2612 -1.8269 0.4365 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5193 -3.1863 0.3279 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8193 -3.6581 0.4443 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4722 -4.0535 0.1043 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1856 -3.5520 -0.0072 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3363 -0.3795 0.0882 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5105 3.9539 1.2519 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6405 5.3843 0.6442 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5850 4.3681 -0.4721 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9473 2.1385 0.3009 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1141 -1.0039 0.2457 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0642 1.9427 1.7154 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2936 2.6056 0.8890 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3141 1.6956 -1.2041 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9665 0.5394 -1.3074 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0463 -0.4390 -1.3930 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0488 -1.3308 0.6539 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8054 -1.3921 -2.0672 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3085 -2.3607 -1.6334 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2848 -0.5510 -1.4778 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5043 -3.4892 -0.5999 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0217 -2.8498 1.7186 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2596 -2.1455 1.8550 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2441 -4.4517 1.9158 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3844 -2.0513 0.1653 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4891 -3.7627 -1.1135 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3980 2.9578 -1.4856 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8932 4.2371 -0.9015 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6460 4.6474 0.7074 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4697 6.3015 -0.1222 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2052 4.3173 0.8545 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3871 3.1427 2.7611 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5570 -3.5161 -0.3375 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7421 -0.2959 0.4026 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0731 -1.1556 0.6095 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5752 -3.0103 0.6078 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6875 -5.1072 0.0221 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4148 -4.2653 -0.1798 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 1 0 7 9 2 0 9 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 18 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 13 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 6 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 39 41 1 0 41 42 2 0 35 43 1 0 9 3 1 0 30 11 1 0 42 36 1 0 43 5 1 0 24 16 1 0 1 44 1 0 1 45 1 0 1 46 1 0 4 47 1 0 8 48 1 0 11 49 1 1 13 50 1 1 14 51 1 0 14 52 1 0 16 53 1 6 18 54 1 1 19 55 1 0 19 56 1 0 19 57 1 0 20 58 1 6 21 59 1 0 22 60 1 1 23 61 1 0 24 62 1 1 25 63 1 0 26 64 1 6 27 65 1 0 28 66 1 1 29 67 1 0 30 68 1 6 31 69 1 0 34 70 1 0 37 71 1 0 38 72 1 0 40 73 1 0 41 74 1 0 42 75 1 0 M END

Standard InCHIKey	IAXGLXFIQSEJPB-MBHQVIDASA-N
Standard InCHI	InChI=1S/C28H32O15/c1-10-19(31)22(34)24(36)27(40-10)39-9-17-20(32)23(35)25(37)28(42-17)43-26-16(38-2)8-15-18(21(26)33)13(30)7-14(41-15)11-3-5-12(29)6-4-11/h3-8,10,17,19-20,22-25,27-29,31-37H,9H2,1-2H3/t10-,17+,19-,20+,22+,23-,24+,25+,27+,28-/m0/s1
SMILES	COC1=CC2=C(C(O)=C1O[C@@H]1O[C@H](CO[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]1O)C(=O)C=C(C1=CC=C(O)C=C1)O2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	608.17	Volume:	560.823 ? Van der Waals volume.
Dense:	1.084	LogP:	0.528 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.993 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.694 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	238.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.159	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.686	Fsp³:	0.464
MCE-18:	118.585 ? 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:	0.588	Fluc inhibitor:	0.27 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.844 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.7 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.058	Promiscuous compounds:	0.376

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.291	MDCK Permeability:	-5.311
Pgp-inhibitor:	0.0	Pgp-substrate:	0.767
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):	0.216
20% Bioavailability (F20%):	0.283	30% Bioavailability (F30%):	0.896
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.284
Plasma Protein Binding (PPB):	83.852%	Volume Distribution (VD):	-0.004
Fu:	13.835% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.14
BSEP inhibitor:	0.014

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.02
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.975
HLM stability:	0.026 ? 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):

1.862

Half-life (T1/2):

4.199

ADMET: Toxicity

hERG Blockers:	0.033	hERG Blockers (10um):	0.202
Human Hepatotoxicity (H-HT):	0.303	Drug-induced Liver Injury (DILI):	0.803
AMES Toxicity:	0.775	Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.041	Skin Sensitization:	0.922
Carcinogencity:	0.05	Eye Corrosion:	0.0
Eye Irritation:	0.123	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.933
Hematotoxicity:	0.076	Drug-induced Nephrotoxicity:	0.215
Genotoxicity:	0.588	RPMI-8226 Immunitoxicity:	0.125
A549 Cytotoxicity:	0.205	Hek293 Cytotoxicity:	0.497
BCF:	0.383 ? 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:	2.926 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.447 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.55 ? 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
NPO10824	Pterogyne nitens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159272]
NPO10824	Pterogyne nitens	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19159272]
NPO10824	Pterogyne nitens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10824	Pterogyne nitens	Species	Fabaceae	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

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

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 NPC592710 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	18927
0.1-0.2	26767
0.2-0.3	3048
0.3-0.4	689
0.4-0.5	289
0.5-0.6	88
0.6-0.7	31
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8272	Intermediate Similarity	NPC172807
0.8214	Intermediate Similarity	NPC204693
0.7976	Intermediate Similarity	NPC44931
0.7326	Intermediate Similarity	NPC254540
0.7273	Intermediate Similarity	NPC22062
0.7273	Intermediate Similarity	NPC473634
0.7273	Intermediate Similarity	NPC138811
0.7195	Intermediate Similarity	NPC93337
0.7079	Intermediate Similarity	NPC210073
0.6818	Remote Similarity	NPC211594
0.6774	Remote Similarity	NPC483707
0.6774	Remote Similarity	NPC209296
0.6706	Remote Similarity	NPC105025
0.663	Remote Similarity	NPC473571
0.663	Remote Similarity	NPC110941
0.6591	Remote Similarity	NPC99957
0.6562	Remote Similarity	NPC101636
0.6522	Remote Similarity	NPC473512
0.6522	Remote Similarity	NPC129827
0.6452	Remote Similarity	NPC186816
0.6353	Remote Similarity	NPC331652
0.6322	Remote Similarity	NPC45638
0.6289	Remote Similarity	NPC473073
0.6237	Remote Similarity	NPC173582
0.6237	Remote Similarity	NPC265885
0.6237	Remote Similarity	NPC181465
0.6237	Remote Similarity	NPC215710
0.6237	Remote Similarity	NPC473438
0.6237	Remote Similarity	NPC253788
0.6211	Remote Similarity	NPC475366
0.617	Remote Similarity	NPC65563
0.617	Remote Similarity	NPC470949
0.6146	Remote Similarity	NPC470443
0.6092	Remote Similarity	NPC58053
0.6082	Remote Similarity	NPC473623
0.6064	Remote Similarity	NPC67105
0.6061	Remote Similarity	NPC298171
0.6042	Remote Similarity	NPC126784
0.6042	Remote Similarity	NPC241423
0.602	Remote Similarity	NPC488089
0.5889	Remote Similarity	NPC201292
0.5882	Remote Similarity	NPC11468
0.5876	Remote Similarity	NPC64051
0.5844	Remote Similarity	NPC120163
0.5833	Remote Similarity	NPC203259
0.5833	Remote Similarity	NPC33054
0.5833	Remote Similarity	NPC176740
0.5833	Remote Similarity	NPC471725
0.5833	Remote Similarity	NPC134532
0.5833	Remote Similarity	NPC602582
0.5824	Remote Similarity	NPC609451
0.58	Remote Similarity	NPC476472
0.58	Remote Similarity	NPC294815
0.58	Remote Similarity	NPC16194
0.5778	Remote Similarity	NPC186807
0.5741	Remote Similarity	NPC298666
0.5714	Remote Similarity	NPC27942
0.57	Remote Similarity	NPC142142
0.57	Remote Similarity	NPC270675
0.57	Remote Similarity	NPC195685
0.5699	Remote Similarity	NPC602805
0.567	Remote Similarity	NPC303913
0.5657	Remote Similarity	NPC65711
0.5625	Remote Similarity	NPC295613
0.5625	Remote Similarity	NPC187379
0.5625	Remote Similarity	NPC473657
0.5619	Remote Similarity	NPC472993
0.5604	Remote Similarity	NPC27640
0.56	Remote Similarity	NPC473327
0.5591	Remote Similarity	NPC605067
0.5567	Remote Similarity	NPC15358
0.5567	Remote Similarity	NPC227508
0.5566	Remote Similarity	NPC473644
0.5556	Remote Similarity	NPC39360
0.5556	Remote Similarity	NPC19709
0.5556	Remote Similarity	NPC29763
0.5556	Remote Similarity	NPC210003
0.5542	Remote Similarity	NPC469622
0.5534	Remote Similarity	NPC472994
0.5514	Remote Similarity	NPC311850
0.551	Remote Similarity	NPC233994
0.551	Remote Similarity	NPC65003
0.5495	Remote Similarity	NPC146792
0.5437	Remote Similarity	NPC470449
0.5435	Remote Similarity	NPC46420
0.5435	Remote Similarity	NPC24043
0.5426	Remote Similarity	NPC181616
0.5421	Remote Similarity	NPC25523
0.5408	Remote Similarity	NPC39834
0.54	Remote Similarity	NPC46202
0.54	Remote Similarity	NPC284277
0.54	Remote Similarity	NPC475497
0.5364	Remote Similarity	NPC68592
0.5347	Remote Similarity	NPC211532
0.5347	Remote Similarity	NPC488364
0.534	Remote Similarity	NPC470447
0.5306	Remote Similarity	NPC471079
0.5294	Remote Similarity	NPC229409
0.5275	Remote Similarity	NPC114740
0.5269	Remote Similarity	NPC610763
0.5258	Remote Similarity	NPC477848
0.5253	Remote Similarity	NPC47923
0.5248	Remote Similarity	NPC488073
0.5248	Remote Similarity	NPC488074
0.5217	Remote Similarity	NPC108831
0.5217	Remote Similarity	NPC182634
0.5196	Remote Similarity	NPC12013
0.5196	Remote Similarity	NPC11432
0.5196	Remote Similarity	NPC477613
0.5192	Remote Similarity	NPC475382
0.5179	Remote Similarity	NPC198199
0.5161	Remote Similarity	NPC259152
0.5109	Remote Similarity	NPC473043
0.5106	Remote Similarity	NPC181712
0.5104	Remote Similarity	NPC606560
0.5093	Remote Similarity	NPC189564
0.5089	Remote Similarity	NPC488086
0.5086	Remote Similarity	NPC262222
0.5054	Remote Similarity	NPC249281
0.5054	Remote Similarity	NPC83283
0.5053	Remote Similarity	NPC198324
0.5052	Remote Similarity	NPC607707
0.505	Remote Similarity	NPC475155
0.505	Remote Similarity	NPC156869
0.5048	Remote Similarity	NPC477629
0.5047	Remote Similarity	NPC470455
0.5045	Remote Similarity	NPC488087
0.5043	Remote Similarity	NPC120952

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC592710 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5131
0.1-0.2	3944
0.2-0.3	63
0.3-0.4	7
0.4-0.5	0
0.5-0.6	4
0.6-0.7	1
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
0.6774	Remote Similarity	NPD7054	Phase 4
0.5882	Remote Similarity	NPD7472	Pre-clinical
0.5833	Remote Similarity	NPD6797	Phase 2
0.5644	Remote Similarity	NPD7251	Phase 2
0.5283	Remote Similarity	NPD7808	Phase 3

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