NPASS Compound

Natural Product: NPC562689

Natural Product ID	NPC562689
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Tamarixetin 3-robinobioside
IUPAC Name	5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)-3-[(2~{S},5~{R})-3,4,5-trihydroxy-6-[[(2~{R},4~{S},5~{R})-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 76 80 0 0 0 0 0 0 0 0999 V2000 -8.3413 3.0040 -1.9971 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3824 2.4566 -1.3327 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4679 1.5872 -0.9528 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3138 0.3793 -1.6381 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3722 -0.5077 -1.2387 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5270 -0.3010 -0.1716 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6006 -1.3322 0.2477 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5483 -1.1357 1.0619 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2029 0.1011 1.5908 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1974 0.8197 0.8596 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0347 0.6765 1.5718 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0352 0.8080 0.6349 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4247 0.7730 1.2781 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3236 0.8470 0.2456 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6677 0.8092 0.6717 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3190 1.8573 0.1133 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6732 1.7991 -0.0181 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4396 2.1535 1.2255 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2096 0.4963 -0.5911 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7153 0.3502 -1.8739 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6542 -0.6444 0.2698 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0819 -1.8458 -0.2684 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1670 -0.5451 0.1320 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4803 -1.5735 0.7155 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7961 2.0674 -0.1347 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9481 2.8128 -0.3848 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1655 2.9854 0.6310 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2812 4.1959 -0.0019 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5227 2.2584 0.7006 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1740 2.6018 -0.4680 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7497 -2.2500 1.3761 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7742 -2.0628 2.1378 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0108 -3.4965 0.8795 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2272 -4.5797 1.1820 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1300 -4.4652 2.0152 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5403 -5.8017 0.6449 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6309 -5.9584 -0.1937 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9315 -7.2037 -0.7274 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3976 -4.8556 -0.4789 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1201 -3.5940 0.0409 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8484 -2.5768 -0.2410 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6700 0.8738 0.5010 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6183 1.8168 0.1331 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7882 3.0242 0.7950 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3330 4.1459 -2.0211 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3805 2.7646 -1.5676 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4054 2.7554 -3.1143 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9788 0.2053 -2.4946 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2623 -1.4574 -1.7862 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0073 0.3586 -0.1159 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9378 -0.0565 -0.0701 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4974 -0.1512 1.8790 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5104 1.6273 1.9949 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6525 0.7755 1.7872 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9451 2.5622 -0.8033 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9137 3.1439 1.0720 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7349 2.2985 2.0977 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1890 1.3745 1.5022 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3066 0.5445 -0.5729 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5700 -0.6052 -2.1149 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9444 -0.4983 1.3304 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7405 -2.3189 0.3179 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9135 -0.5148 -0.9509 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6838 -1.8603 0.2017 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2588 1.8148 -1.0812 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1029 2.7616 -1.3677 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2038 3.1262 1.6553 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6068 4.0641 -0.9289 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0528 2.6913 1.5543 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7220 2.2411 -1.2504 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6552 -3.9161 1.6737 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9396 -6.6952 0.8611 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7927 -7.3067 -1.7388 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2388 -4.9866 -1.1318 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0831 1.1575 1.3750 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3929 3.1293 1.7037 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 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 17 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 12 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 8 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 34 36 1 0 36 37 2 0 37 38 1 0 37 39 1 0 39 40 2 0 40 41 1 0 6 42 1 0 42 43 2 0 43 44 1 0 43 3 1 0 41 7 1 0 29 10 1 0 40 33 1 0 23 15 1 0 1 45 1 0 1 46 1 0 1 47 1 0 4 48 1 0 5 49 1 0 10 50 1 6 12 51 1 0 13 52 1 0 13 53 1 0 15 54 1 1 17 55 1 0 18 56 1 0 18 57 1 0 18 58 1 0 19 59 1 6 20 60 1 0 21 61 1 1 22 62 1 0 23 63 1 0 24 64 1 0 25 65 1 6 26 66 1 0 27 67 1 0 28 68 1 0 29 69 1 0 30 70 1 0 35 71 1 0 36 72 1 0 38 73 1 0 39 74 1 0 42 75 1 0 44 76 1 0 M END

Standard InCHIKey	KEIZXGINFPDITQ-YTFRHVLBSA-N
Standard InCHI	InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(41-9)40-8-16-19(33)22(36)24(38)28(43-16)44-26-20(34)17-13(31)6-11(29)7-15(17)42-25(26)10-3-4-14(39-2)12(30)5-10/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9?,16?,18-,19-,21-,22?,23?,24?,27+,28-/m0/s1
SMILES	COC1=CC=C(C2=C(O[C@@H]3OC(CO[C@@H]4OC(C)[C@H](O)[C@H](O)C4O)[C@H](O)C(O)C3O)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.17	Volume:	569.614 ? Van der Waals volume.
Dense:	1.096	LogP:	0.47 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.107 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.65 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	258.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.147	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.758	Fsp³:	0.464
MCE-18:	122.073 ? 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:	0.617	Fluc inhibitor:	0.202 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.833 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.96 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.063	Promiscuous compounds:	0.308

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.312	MDCK Permeability:	-5.279
Pgp-inhibitor:	0.0	Pgp-substrate:	0.996
PAMPA:	1.0 ? 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):	0.749
20% Bioavailability (F20%):	0.525	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.513
Plasma Protein Binding (PPB):	85.956%	Volume Distribution (VD):	-0.091
Fu:	13.179% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.31
OATP1B3 inhibitor:	0.99	BCRP inhibitor:	0.93
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.557	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.997
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.79 ? 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):

1.047

Half-life (T1/2):

3.012

ADMET: Toxicity

hERG Blockers:	0.027	hERG Blockers (10um):	0.323
Human Hepatotoxicity (H-HT):	0.546	Drug-induced Liver Injury (DILI):	0.96
AMES Toxicity:	0.944	Rat Oral Acute Toxicity:	0.219
Maximum Recommended Daily Dose:	0.48	Skin Sensitization:	0.986
Carcinogencity:	0.236	Eye Corrosion:	0.0
Eye Irritation:	0.142	Respiratory Toxicity:	0.104
Drug-induced Neurotoxicity:	0.032	Ototoxicity:	0.838
Hematotoxicity:	0.05	Drug-induced Nephrotoxicity:	0.127
Genotoxicity:	0.962	RPMI-8226 Immunitoxicity:	0.179
A549 Cytotoxicity:	0.727	Hek293 Cytotoxicity:	0.911
BCF:	0.401 ? 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:	3.005 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.653 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.714 ? 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
NPO51841	Bupleurum spinosum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC562689 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	15787
0.1-0.2	29708
0.2-0.3	3289
0.3-0.4	571
0.4-0.5	241
0.5-0.6	92
0.6-0.7	72
0.7-0.8	0
0.8-0.85	17
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473327
0.8409	Intermediate Similarity	NPC476472
0.8409	Intermediate Similarity	NPC294815
0.8409	Intermediate Similarity	NPC16194
0.8353	Intermediate Similarity	NPC203259
0.8353	Intermediate Similarity	NPC33054
0.8353	Intermediate Similarity	NPC176740
0.8353	Intermediate Similarity	NPC471725
0.8353	Intermediate Similarity	NPC134532
0.8353	Intermediate Similarity	NPC602582
0.8272	Intermediate Similarity	NPC219904
0.8235	Intermediate Similarity	NPC173582
0.8235	Intermediate Similarity	NPC265885
0.8235	Intermediate Similarity	NPC181465
0.8235	Intermediate Similarity	NPC215710
0.8235	Intermediate Similarity	NPC473438
0.8235	Intermediate Similarity	NPC253788
0.8023	Intermediate Similarity	NPC39834
0.7363	Intermediate Similarity	NPC126784
0.7363	Intermediate Similarity	NPC241423
0.7333	Intermediate Similarity	NPC156869
0.7326	Intermediate Similarity	NPC120099
0.7253	Intermediate Similarity	NPC473571
0.7253	Intermediate Similarity	NPC110941
0.7222	Intermediate Similarity	NPC67326
0.7174	Intermediate Similarity	NPC153755
0.7143	Intermediate Similarity	NPC173837
0.7113	Intermediate Similarity	NPC89052
0.7111	Intermediate Similarity	NPC471079
0.7111	Intermediate Similarity	NPC187379
0.7111	Intermediate Similarity	NPC609888
0.7079	Intermediate Similarity	NPC116864
0.7079	Intermediate Similarity	NPC244776
0.7059	Intermediate Similarity	NPC265530
0.7053	Intermediate Similarity	NPC89127
0.7021	Intermediate Similarity	NPC122467
0.6915	Remote Similarity	NPC12013
0.6915	Remote Similarity	NPC470443
0.6915	Remote Similarity	NPC11432
0.6915	Remote Similarity	NPC477613
0.6854	Remote Similarity	NPC223747
0.6818	Remote Similarity	NPC60735
0.6818	Remote Similarity	NPC26230
0.68	Remote Similarity	NPC292019
0.68	Remote Similarity	NPC202908
0.6774	Remote Similarity	NPC65563
0.6774	Remote Similarity	NPC470949
0.6744	Remote Similarity	NPC127546
0.6744	Remote Similarity	NPC57625
0.6744	Remote Similarity	NPC173637
0.6744	Remote Similarity	NPC317489
0.6744	Remote Similarity	NPC223424
0.6744	Remote Similarity	NPC600591
0.6742	Remote Similarity	NPC609478
0.6702	Remote Similarity	NPC186816
0.67	Remote Similarity	NPC189564
0.6667	Remote Similarity	NPC209296
0.6633	Remote Similarity	NPC221342
0.6633	Remote Similarity	NPC476470
0.6629	Remote Similarity	NPC611303
0.6628	Remote Similarity	NPC111929
0.6628	Remote Similarity	NPC320283
0.6628	Remote Similarity	NPC41121
0.66	Remote Similarity	NPC203145
0.6566	Remote Similarity	NPC602448
0.6481	Remote Similarity	NPC192539
0.6458	Remote Similarity	NPC488073
0.6458	Remote Similarity	NPC488074
0.6437	Remote Similarity	NPC135599
0.6437	Remote Similarity	NPC73855
0.6437	Remote Similarity	NPC113968
0.6437	Remote Similarity	NPC328940
0.6437	Remote Similarity	NPC277174
0.6437	Remote Similarity	NPC606877
0.6408	Remote Similarity	NPC303694
0.6389	Remote Similarity	NPC241781
0.6364	Remote Similarity	NPC471669
0.6355	Remote Similarity	NPC162394
0.6339	Remote Similarity	NPC473554
0.6333	Remote Similarity	NPC472459
0.6311	Remote Similarity	NPC477895
0.63	Remote Similarity	NPC470445
0.6264	Remote Similarity	NPC175107
0.625	Remote Similarity	NPC217520
0.625	Remote Similarity	NPC605592
0.6238	Remote Similarity	NPC470446
0.6238	Remote Similarity	NPC223426
0.6204	Remote Similarity	NPC156785
0.62	Remote Similarity	NPC470447
0.62	Remote Similarity	NPC85751
0.62	Remote Similarity	NPC473073
0.62	Remote Similarity	NPC19240
0.6186	Remote Similarity	NPC129264
0.6176	Remote Similarity	NPC81042
0.617	Remote Similarity	NPC95866
0.6162	Remote Similarity	NPC37668
0.6139	Remote Similarity	NPC470449
0.6132	Remote Similarity	NPC139571
0.6111	Remote Similarity	NPC64305
0.6064	Remote Similarity	NPC203050
0.6064	Remote Similarity	NPC225434
0.6064	Remote Similarity	NPC476215
0.6055	Remote Similarity	NPC474522
0.604	Remote Similarity	NPC220173
0.6019	Remote Similarity	NPC214621
0.6019	Remote Similarity	NPC34267
0.6	Remote Similarity	NPC270448
0.6	Remote Similarity	NPC606657
0.5978	Remote Similarity	NPC325555
0.5978	Remote Similarity	NPC226304
0.5966	Remote Similarity	NPC487500
0.5965	Remote Similarity	NPC487499
0.596	Remote Similarity	NPC470125
0.5957	Remote Similarity	NPC209023
0.5941	Remote Similarity	NPC142142
0.5934	Remote Similarity	NPC145038
0.5934	Remote Similarity	NPC56077
0.5934	Remote Similarity	NPC281131
0.5934	Remote Similarity	NPC253662
0.5934	Remote Similarity	NPC179950
0.5934	Remote Similarity	NPC88789
0.5934	Remote Similarity	NPC491374
0.5918	Remote Similarity	NPC22062
0.5918	Remote Similarity	NPC473634
0.5918	Remote Similarity	NPC155877
0.5918	Remote Similarity	NPC138811
0.5917	Remote Similarity	NPC487501
0.587	Remote Similarity	NPC305811
0.5856	Remote Similarity	NPC480444
0.5825	Remote Similarity	NPC292929
0.5825	Remote Similarity	NPC287889
0.5824	Remote Similarity	NPC77672
0.5824	Remote Similarity	NPC133671
0.5824	Remote Similarity	NPC135391
0.5824	Remote Similarity	NPC78263
0.5824	Remote Similarity	NPC250069
0.5818	Remote Similarity	NPC480445
0.5816	Remote Similarity	NPC163242
0.5816	Remote Similarity	NPC272068
0.5802	Remote Similarity	NPC82325
0.5773	Remote Similarity	NPC251417
0.5763	Remote Similarity	NPC487502
0.5755	Remote Similarity	NPC470451
0.5728	Remote Similarity	NPC76831
0.5714	Remote Similarity	NPC470455
0.5701	Remote Similarity	NPC48984
0.57	Remote Similarity	NPC204693
0.5699	Remote Similarity	NPC46420
0.5699	Remote Similarity	NPC271692
0.5667	Remote Similarity	NPC276222
0.5667	Remote Similarity	NPC274618
0.5667	Remote Similarity	NPC118284
0.5667	Remote Similarity	NPC608147
0.5657	Remote Similarity	NPC471748
0.5657	Remote Similarity	NPC67105
0.5652	Remote Similarity	NPC19388
0.5652	Remote Similarity	NPC240431
0.5652	Remote Similarity	NPC55786
0.5648	Remote Similarity	NPC480441
0.5648	Remote Similarity	NPC25523
0.5644	Remote Similarity	NPC154741
0.5641	Remote Similarity	NPC275977
0.5638	Remote Similarity	NPC21100
0.5625	Remote Similarity	NPC488740
0.5625	Remote Similarity	NPC488736
0.5625	Remote Similarity	NPC488733
0.5604	Remote Similarity	NPC67037
0.5604	Remote Similarity	NPC255615
0.5586	Remote Similarity	NPC488734
0.5586	Remote Similarity	NPC488735
0.5586	Remote Similarity	NPC488739
0.5586	Remote Similarity	NPC488732
0.5586	Remote Similarity	NPC488738
0.5579	Remote Similarity	NPC159579
0.5556	Remote Similarity	NPC219043
0.5556	Remote Similarity	NPC54802
0.5556	Remote Similarity	NPC197304
0.5556	Remote Similarity	NPC29958
0.5556	Remote Similarity	NPC139320
0.5546	Remote Similarity	NPC72554
0.5526	Remote Similarity	NPC488737
0.55	Remote Similarity	NPC44931
0.55	Remote Similarity	NPC227508
0.5495	Remote Similarity	NPC288084
0.549	Remote Similarity	NPC296018
0.5474	Remote Similarity	NPC216496
0.547	Remote Similarity	NPC21359
0.547	Remote Similarity	NPC460984
0.5446	Remote Similarity	NPC210073
0.5426	Remote Similarity	NPC158674
0.5417	Remote Similarity	NPC191306
0.5417	Remote Similarity	NPC30011
0.5417	Remote Similarity	NPC182121
0.5405	Remote Similarity	NPC470718
0.5392	Remote Similarity	NPC255157
0.5392	Remote Similarity	NPC259896
0.5385	Remote Similarity	NPC25946
0.5378	Remote Similarity	NPC231787
0.5377	Remote Similarity	NPC36138
0.537	Remote Similarity	NPC121703

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC562689 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4750
0.1-0.2	4338
0.2-0.3	50
0.3-0.4	5
0.4-0.5	2
0.5-0.6	1
0.6-0.7	3
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8353	Intermediate Similarity	NPD6797	Phase 2
0.6667	Remote Similarity	NPD7054	Phase 4
0.6364	Remote Similarity	NPD7251	Phase 2
0.6275	Remote Similarity	NPD7808	Phase 3
0.5962	Remote Similarity	NPD7472	Pre-clinical

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