NPASS Compound

Natural Product: NPC577567

Natural Product ID	NPC577567
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{S},3~{S},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-[5-hydroxy-2-[3-methoxy-4-[(2~{S},3~{S},4~{R},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-phenyl]-4-oxo-chromen-7-yl]oxy-tetrahydropyran-2-carboxylic acid
IUPAC Name	(2~{S},3~{S},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-[5-hydroxy-2-[3-methoxy-4-[(2~{S},3~{S},4~{R},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-phenyl]-4-oxo-chromen-7-yl]oxy-tetrahydropyran-2-carboxylic acid
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 74 78 0 0 0 0 0 0 0 0999 V2000 2.4927 2.2727 -0.7941 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5616 1.3693 -0.7288 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3060 0.0470 -0.3857 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9950 -0.3533 -0.1149 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6670 -1.6449 0.2313 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2804 -2.0074 0.5014 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1095 -3.2769 0.8609 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4472 -3.6060 1.1166 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8058 -4.7478 1.4411 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3989 -2.6160 1.0013 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7416 -2.8605 1.2366 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1674 -4.1371 1.6026 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6808 -1.8286 1.1090 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2578 -0.5805 0.7504 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1357 0.4571 0.6125 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5120 0.4109 0.7871 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1255 0.7636 -0.4365 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5116 0.7080 -0.3091 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1618 0.7714 -1.6276 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5014 0.8651 -2.6836 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5457 0.7264 -1.7127 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9931 1.8706 0.5464 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.7947 1.4092 1.5805 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7323 2.5040 1.1477 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9927 3.0278 0.0883 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9879 1.3929 1.8481 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8537 0.7795 2.7547 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8848 -0.3578 0.5163 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9534 -1.3636 0.6386 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6795 -1.1174 0.4115 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7043 -2.5353 0.2989 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0069 -2.1897 0.0418 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3456 -0.8671 -0.3129 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6555 -0.6049 -0.5511 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3950 0.4893 -0.9015 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0722 0.3926 -2.0821 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2808 0.9827 -2.2274 C 0 0 2 0 0 0 0 0 0 0 0 0 8.7630 0.7204 -3.6432 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3205 0.4559 -1.2504 C 0 0 2 0 0 0 0 0 0 0 0 0 10.0540 -0.5895 -1.7749 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6214 0.0888 0.0551 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4636 0.2144 1.1519 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3640 0.9199 0.1995 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8007 0.8034 1.4577 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6553 1.9022 -1.4202 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0380 2.4780 0.2196 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7880 3.2695 -1.1735 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1850 0.3620 -0.1728 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6143 -4.0699 0.9577 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4860 -4.2433 2.5556 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7071 -2.0482 1.2986 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9308 -0.5815 1.0423 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8290 -0.2720 0.1563 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0492 0.4614 -2.5564 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4970 2.6031 -0.1049 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3770 2.1221 1.9086 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0192 3.3149 1.8472 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5674 3.1289 -0.7126 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1593 1.8192 2.4261 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8523 -0.2053 2.6709 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5906 0.6489 0.2328 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5016 -3.5874 0.5721 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8212 -2.9318 0.1043 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7186 1.3839 -1.0165 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1861 2.0803 -2.1299 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3194 1.4632 -4.3537 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3405 -0.2713 -3.9668 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8658 0.6966 -3.7063 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0038 1.2855 -1.0237 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4468 -1.2666 -2.1906 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3282 -0.9729 -0.0270 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1865 0.8667 0.9187 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6554 1.9635 -0.0391 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2349 1.4413 2.0740 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 1 0 6 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 2 0 11 12 1 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 18 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 14 28 1 0 28 29 2 0 29 30 1 0 5 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 33 3 1 0 43 35 1 0 30 6 1 0 29 10 1 0 26 16 1 0 1 45 1 0 1 46 1 0 1 47 1 0 4 48 1 0 7 49 1 0 12 50 1 0 13 51 1 0 16 52 1 1 18 53 1 1 21 54 1 0 22 55 1 6 23 56 1 0 24 57 1 1 25 58 1 0 26 59 1 1 27 60 1 0 28 61 1 0 31 62 1 0 32 63 1 0 35 64 1 6 37 65 1 6 38 66 1 0 38 67 1 0 38 68 1 0 39 69 1 1 40 70 1 0 41 71 1 6 42 72 1 0 43 73 1 6 44 74 1 0 M END

Standard InCHIKey	ZENWXUBCITVBTM-DAVBIMNCSA-N
Standard InCHI	InChI=1S/C28H30O16/c1-9-19(31)20(32)23(35)27(40-9)43-14-4-3-10(5-16(14)39-2)15-8-13(30)18-12(29)6-11(7-17(18)42-15)41-28-24(36)21(33)22(34)25(44-28)26(37)38/h3-9,19-25,27-29,31-36H,1-2H3,(H,37,38)/t9-,19+,20-,21+,22+,23+,24-,25+,27+,28-/m1/s1
SMILES	COC1=CC(C2=CC(=O)C3=C(O)C=C(O[C@@H]4O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]4O)C=C3O2)=CC=C1O[C@@H]1O[C@H](C)[C@H](O)[C@@H](O)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	622.15	Volume:	566.977 ? Van der Waals volume.
Dense:	1.097	LogP:	0.856 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.411 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.499 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	31.0
TPSA:	255.27 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.152	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.698	Fsp³:	0.429
MCE-18:	122.5 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.483	Fluc inhibitor:	0.362 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.964 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.93 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.11	Promiscuous compounds:	0.399

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.276	MDCK Permeability:	-5.318
Pgp-inhibitor:	0.0	Pgp-substrate:	0.984
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):	0.979
20% Bioavailability (F20%):	0.287	30% Bioavailability (F30%):	0.916
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.954
Plasma Protein Binding (PPB):	79.146%	Volume Distribution (VD):	-0.201
Fu:	18.312% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.475
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.224
BSEP inhibitor:	0.0

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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.08
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.004
HLM stability:	0.0 ? 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):

1.056

Half-life (T1/2):

5.283

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.021
Human Hepatotoxicity (H-HT):	0.71	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.967	Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.013	Skin Sensitization:	0.999
Carcinogencity:	0.072	Eye Corrosion:	0.0
Eye Irritation:	0.147	Respiratory Toxicity:	0.019
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.956
Hematotoxicity:	0.447	Drug-induced Nephrotoxicity:	0.934
Genotoxicity:	0.974	RPMI-8226 Immunitoxicity:	0.19
A549 Cytotoxicity:	0.384	Hek293 Cytotoxicity:	0.172
BCF:	0.225 ? 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:	2.959 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.349 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.534 ? 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
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33264011]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	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

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 NPC577567 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	16620
0.1-0.2	30002
0.2-0.3	2457
0.3-0.4	529
0.4-0.5	182
0.5-0.6	54
0.6-0.7	13
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
0.7586	Intermediate Similarity	NPC608742
0.6923	Remote Similarity	NPC607707
0.6889	Remote Similarity	NPC282169
0.6889	Remote Similarity	NPC20505
0.6813	Remote Similarity	NPC243930
0.6517	Remote Similarity	NPC473043
0.6444	Remote Similarity	NPC19709
0.6333	Remote Similarity	NPC331652
0.62	Remote Similarity	NPC46202
0.6022	Remote Similarity	NPC95090
0.6022	Remote Similarity	NPC27408
0.6	Remote Similarity	NPC22062
0.6	Remote Similarity	NPC473634
0.6	Remote Similarity	NPC138811
0.5957	Remote Similarity	NPC181712
0.5849	Remote Similarity	NPC253685
0.5833	Remote Similarity	NPC609451
0.5773	Remote Similarity	NPC22832
0.5769	Remote Similarity	NPC209296
0.5769	Remote Similarity	NPC229409
0.5728	Remote Similarity	NPC64051
0.5714	Remote Similarity	NPC88023
0.5714	Remote Similarity	NPC311830
0.5612	Remote Similarity	NPC601144
0.56	Remote Similarity	NPC600989
0.5567	Remote Similarity	NPC27942
0.5534	Remote Similarity	NPC210073
0.5521	Remote Similarity	NPC189142
0.5521	Remote Similarity	NPC77660
0.5514	Remote Similarity	NPC475382
0.551	Remote Similarity	NPC237435
0.551	Remote Similarity	NPC611303
0.55	Remote Similarity	NPC190003
0.5465	Remote Similarity	NPC195202
0.5455	Remote Similarity	NPC43211
0.5437	Remote Similarity	NPC44931
0.5417	Remote Similarity	NPC261866
0.5417	Remote Similarity	NPC39360
0.5417	Remote Similarity	NPC29763
0.5417	Remote Similarity	NPC210003
0.5417	Remote Similarity	NPC238376
0.54	Remote Similarity	NPC309025
0.537	Remote Similarity	NPC195257
0.537	Remote Similarity	NPC479765
0.5327	Remote Similarity	NPC473623
0.5306	Remote Similarity	NPC271692
0.5283	Remote Similarity	NPC475366
0.5278	Remote Similarity	NPC479766
0.5278	Remote Similarity	NPC488089
0.5258	Remote Similarity	NPC108831
0.5258	Remote Similarity	NPC182634
0.5204	Remote Similarity	NPC158674
0.5189	Remote Similarity	NPC204693
0.5189	Remote Similarity	NPC115674
0.5179	Remote Similarity	NPC11468
0.5152	Remote Similarity	NPC186807
0.5152	Remote Similarity	NPC46420
0.5149	Remote Similarity	NPC115760
0.5149	Remote Similarity	NPC610187
0.5146	Remote Similarity	NPC211594
0.5102	Remote Similarity	NPC58053
0.5102	Remote Similarity	NPC249281
0.51	Remote Similarity	NPC182045
0.51	Remote Similarity	NPC101191
0.5094	Remote Similarity	NPC65003
0.505	Remote Similarity	NPC135277
0.505	Remote Similarity	NPC210094
0.5045	Remote Similarity	NPC101636

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC577567 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3739
0.1-0.2	5314
0.2-0.3	87
0.3-0.4	2
0.4-0.5	6
0.5-0.6	2
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
0.5769	Remote Similarity	NPD7054	Phase 4
0.551	Remote Similarity	NPD4338	Clinical (unspecified phase)

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