NPASS Compound

Natural Product: NPC539496

Natural Product ID	NPC539496
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-[(2~{S},3~{S},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-[(2~{S},3~{S},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{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 73 77 0 0 0 0 0 0 0 0999 V2000 -7.1473 2.0024 -1.9855 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2671 0.5148 -2.0070 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0571 -0.1558 -2.0525 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2970 0.0351 -0.8887 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7798 1.3041 -0.8521 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4329 1.4128 -0.9797 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6103 0.7661 0.0947 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2411 0.9428 -0.2748 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5785 -0.1477 0.3250 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7658 0.0082 0.3550 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8502 -0.6090 -0.1317 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1281 -0.1012 0.1471 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2832 -0.6832 -0.3192 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1550 -1.8149 -1.0928 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9231 -2.3495 -1.3927 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8502 -3.5075 -2.1876 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7668 -1.7365 -0.9050 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5854 -2.3662 -1.2731 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3323 -2.3929 -1.5572 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2358 -3.4261 -2.2647 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5399 -1.8090 -1.2216 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5993 -0.6749 -0.4426 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8787 -0.0375 -0.0742 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8371 1.0907 0.7040 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9945 1.7398 1.0886 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2156 1.2349 0.6762 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3750 1.9018 1.0730 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2857 0.1154 -0.0976 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5160 -0.3677 -0.4954 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1019 -0.5140 -0.4672 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4625 -0.1792 -0.0373 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0839 -0.3427 1.7409 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0651 -0.7742 2.5902 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6311 0.9265 2.3224 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5914 1.8455 2.4818 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7109 1.4551 1.4160 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9405 1.3970 2.0334 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0712 -0.3364 0.3422 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3585 -1.2032 1.1853 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4259 -0.9342 0.0018 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1231 -1.0624 1.2044 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1435 0.0698 -0.8589 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4858 1.1459 -0.0367 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9284 2.4265 -1.0027 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4564 2.3554 -2.7853 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1582 2.4143 -2.2760 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8131 0.2317 -2.9404 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4633 -0.7203 -0.9958 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0427 1.0547 -1.9537 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1833 2.5086 -0.9548 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8444 -0.3061 0.1727 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8899 -1.0218 -0.2676 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2468 0.7905 0.7559 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7961 -4.3788 -1.6710 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1715 -2.2833 -2.1948 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4528 -2.2789 -1.5965 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8871 1.4775 1.0209 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9885 2.6246 1.6976 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0624 1.3865 1.6181 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1252 -0.8146 0.1529 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1720 -1.3963 -1.0780 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8637 -1.1179 1.7271 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5822 -0.0664 2.7527 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1008 0.6842 3.3140 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7139 2.2990 3.3632 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5422 2.5544 1.1938 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5525 2.1262 1.7802 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2983 0.5679 0.9408 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5428 -1.0190 2.1400 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3233 -1.9187 -0.4735 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6704 -0.6228 1.9577 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0910 -0.3942 -1.1913 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6462 0.8510 0.9074 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 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 15 17 2 0 17 18 1 0 14 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 26 28 1 0 28 29 1 0 28 30 2 0 22 31 1 0 9 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 4 38 1 0 38 39 1 0 38 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 42 2 1 0 36 7 1 0 17 11 1 0 30 23 1 0 31 13 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 6 4 48 1 6 6 49 1 0 6 50 1 0 7 51 1 1 9 52 1 6 12 53 1 0 16 54 1 0 18 55 1 0 21 56 1 0 24 57 1 0 25 58 1 0 27 59 1 0 29 60 1 0 30 61 1 0 32 62 1 6 33 63 1 0 34 64 1 1 35 65 1 0 36 66 1 6 37 67 1 0 38 68 1 1 39 69 1 0 40 70 1 6 41 71 1 0 42 72 1 6 43 73 1 0 M END

Standard InCHIKey	CWIWYXBNBCTFOK-WZSWBFJISA-N
Standard InCHI	InChI=1S/C27H30O16/c1-8-18(31)22(35)24(37)26(40-8)39-7-16-20(33)23(36)25(38)27(43-16)42-15-6-14-17(21(34)19(15)32)12(30)5-13(41-14)9-2-3-10(28)11(29)4-9/h2-6,8,16,18,20,22-29,31-38H,7H2,1H3/t8-,16-,18+,20-,22+,23+,24-,25+,26-,27-/m1/s1
SMILES	C[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=CC4=C(C(O)=C3O)C(=O)C=C(C3=CC=C(O)C(O)=C3)O4)[C@@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.15	Volume:	552.318 ? Van der Waals volume.
Dense:	1.105	LogP:	-0.293 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.519 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.367 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	269.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.14	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.812	Fsp³:	0.444
MCE-18:	122.949 ? 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:	1
Colloidal aggregators:	0.616	Fluc inhibitor:	0.315 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.937 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.62 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.156	Promiscuous compounds:	0.583

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.442	MDCK Permeability:	-5.037
Pgp-inhibitor:	0.0	Pgp-substrate:	0.799
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):	0.161
20% Bioavailability (F20%):	0.839	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.297
Plasma Protein Binding (PPB):	82.303%	Volume Distribution (VD):	0.033
Fu:	14.234% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.99
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.722
BSEP inhibitor:	0.113

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:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.982
HLM stability:	0.033 ? 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):

1.276

Half-life (T1/2):

5.662

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.453
Human Hepatotoxicity (H-HT):	0.157	Drug-induced Liver Injury (DILI):	0.496
AMES Toxicity:	0.486	Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.064	Skin Sensitization:	0.889
Carcinogencity:	0.025	Eye Corrosion:	0.0
Eye Irritation:	0.42	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.978
Hematotoxicity:	0.02	Drug-induced Nephrotoxicity:	0.165
Genotoxicity:	0.211	RPMI-8226 Immunitoxicity:	0.049
A549 Cytotoxicity:	0.231	Hek293 Cytotoxicity:	0.114
BCF:	0.571 ? 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:	3.2 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.976 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.148 ? 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
NPO27345	Crocus minimus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27345	Crocus minimus	Species	Iridaceae	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 NPC539496 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	21964
0.1-0.2	24339
0.2-0.3	2649
0.3-0.4	542
0.4-0.5	249
0.5-0.6	80
0.6-0.7	25
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	Natural Product ID
0.8	Intermediate Similarity	NPC210073
0.7528	Intermediate Similarity	NPC470443
0.7229	Intermediate Similarity	NPC58716
0.7079	Intermediate Similarity	NPC44931
0.6977	Remote Similarity	NPC181616
0.6882	Remote Similarity	NPC209296
0.6703	Remote Similarity	NPC67105
0.663	Remote Similarity	NPC22062
0.663	Remote Similarity	NPC473634
0.663	Remote Similarity	NPC138811
0.6559	Remote Similarity	NPC204693
0.6484	Remote Similarity	NPC254540
0.6452	Remote Similarity	NPC3583
0.6421	Remote Similarity	NPC65711
0.6395	Remote Similarity	NPC19709
0.6322	Remote Similarity	NPC146792
0.6277	Remote Similarity	NPC203259
0.6277	Remote Similarity	NPC33054
0.6277	Remote Similarity	NPC176740
0.6277	Remote Similarity	NPC471725
0.6277	Remote Similarity	NPC134532
0.6277	Remote Similarity	NPC602582
0.6224	Remote Similarity	NPC473073
0.6146	Remote Similarity	NPC126784
0.6146	Remote Similarity	NPC241423
0.6042	Remote Similarity	NPC186816
0.6023	Remote Similarity	NPC45618
0.6022	Remote Similarity	NPC477848
0.6	Remote Similarity	NPC227508
0.5938	Remote Similarity	NPC65563
0.5938	Remote Similarity	NPC470949
0.5889	Remote Similarity	NPC245014
0.5859	Remote Similarity	NPC229409
0.5842	Remote Similarity	NPC101636
0.5833	Remote Similarity	NPC173582
0.5833	Remote Similarity	NPC265885
0.5833	Remote Similarity	NPC181465
0.5833	Remote Similarity	NPC215710
0.5833	Remote Similarity	NPC473438
0.5833	Remote Similarity	NPC253788
0.5816	Remote Similarity	NPC475366
0.5745	Remote Similarity	NPC190003
0.5728	Remote Similarity	NPC603856
0.5684	Remote Similarity	NPC172807
0.567	Remote Similarity	NPC39834
0.566	Remote Similarity	NPC480441
0.5612	Remote Similarity	NPC473512
0.5604	Remote Similarity	NPC189142
0.5604	Remote Similarity	NPC77660
0.5588	Remote Similarity	NPC476472
0.5588	Remote Similarity	NPC294815
0.5588	Remote Similarity	NPC16194
0.5556	Remote Similarity	NPC473043
0.5556	Remote Similarity	NPC115674
0.5556	Remote Similarity	NPC331652
0.5556	Remote Similarity	NPC473571
0.5556	Remote Similarity	NPC110941
0.5545	Remote Similarity	NPC473623
0.5543	Remote Similarity	NPC45638
0.5534	Remote Similarity	NPC298171
0.5524	Remote Similarity	NPC11468
0.55	Remote Similarity	NPC162313
0.549	Remote Similarity	NPC488089
0.5484	Remote Similarity	NPC201292
0.5455	Remote Similarity	NPC129827
0.5455	Remote Similarity	NPC156869
0.5408	Remote Similarity	NPC187379
0.5405	Remote Similarity	NPC198199
0.5392	Remote Similarity	NPC122467
0.5392	Remote Similarity	NPC483707
0.5392	Remote Similarity	NPC473327
0.5368	Remote Similarity	NPC43211
0.5361	Remote Similarity	NPC211594
0.5354	Remote Similarity	NPC67326
0.5347	Remote Similarity	NPC488073
0.5326	Remote Similarity	NPC238376
0.5312	Remote Similarity	NPC99957
0.53	Remote Similarity	NPC218488
0.53	Remote Similarity	NPC303913
0.5288	Remote Similarity	NPC89127
0.5268	Remote Similarity	NPC298666
0.5263	Remote Similarity	NPC120952
0.5234	Remote Similarity	NPC599948
0.5229	Remote Similarity	NPC473644
0.5229	Remote Similarity	NPC25523
0.5213	Remote Similarity	NPC84265
0.5213	Remote Similarity	NPC271692
0.52	Remote Similarity	NPC275454
0.5196	Remote Similarity	NPC488074
0.5196	Remote Similarity	NPC64051
0.5192	Remote Similarity	NPC142142
0.5182	Remote Similarity	NPC311850
0.5149	Remote Similarity	NPC233994
0.5138	Remote Similarity	NPC292019
0.5138	Remote Similarity	NPC202908
0.5106	Remote Similarity	NPC168822
0.5104	Remote Similarity	NPC237435
0.51	Remote Similarity	NPC473657
0.5096	Remote Similarity	NPC150767
0.5094	Remote Similarity	NPC470445
0.5053	Remote Similarity	NPC27640
0.5051	Remote Similarity	NPC294629
0.5051	Remote Similarity	NPC116864
0.5051	Remote Similarity	NPC244776
0.5051	Remote Similarity	NPC131407
0.5048	Remote Similarity	NPC270675
0.5048	Remote Similarity	NPC195685
0.5047	Remote Similarity	NPC470446
0.5044	Remote Similarity	NPC68592

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC539496 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5611
0.1-0.2	3485
0.2-0.3	43
0.3-0.4	5
0.4-0.5	0
0.5-0.6	3
0.6-0.7	3
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
0.6882	Remote Similarity	NPD7054	Phase 4
0.6277	Remote Similarity	NPD6797	Phase 2
0.6224	Remote Similarity	NPD7251	Phase 2
0.598	Remote Similarity	NPD7472	Pre-clinical
0.5234	Remote Similarity	NPD7808	Phase 3
0.5104	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