NPASS Compound

Natural Product: NPC591853

Natural Product ID	NPC591853
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-2-phenyl-7-[(2~{S},3~{R},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	5-hydroxy-2-phenyl-7-[(2~{S},3~{R},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 70 74 0 0 0 0 0 0 0 0999 V2000 -5.9903 -0.3368 1.1136 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6062 0.1673 -0.2531 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2601 0.3911 -0.4073 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4795 -0.7409 -0.1383 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5983 -1.0103 1.1917 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4772 -0.9745 1.9594 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7478 0.3112 2.0620 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2688 0.8293 0.8693 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0596 1.4953 1.1933 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4319 2.1819 0.1097 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5906 1.9554 -0.5774 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8934 2.7877 -1.6581 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0190 2.6690 -2.4281 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3028 3.5053 -3.4981 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8966 1.6461 -2.0872 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0558 1.4415 -2.7971 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3627 2.1751 -3.7818 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8910 0.4079 -2.4121 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5777 -0.3942 -1.3533 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4487 -1.4805 -0.9430 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6339 -1.7915 -1.5639 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4196 -2.8564 -1.1078 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0416 -3.6242 -0.0337 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8556 -3.3131 0.5876 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0715 -2.2649 0.1469 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4581 -0.1638 -0.7012 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6444 0.8009 -1.0334 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4799 0.9673 -0.2813 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2350 2.3441 2.4310 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4913 1.8661 3.5216 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6461 2.6208 2.8119 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1853 3.7422 2.1644 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5537 1.4154 2.7087 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0933 1.0415 3.9340 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0045 -1.8845 -1.0091 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9512 -2.5275 -1.6643 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9813 -1.4161 -2.0439 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5401 -2.5793 -2.6163 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1283 -0.7100 -1.3493 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0312 -1.6266 -0.8551 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4531 0.2310 1.8905 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9083 -1.4251 1.2039 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0804 -0.0788 1.2519 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1085 1.1630 -0.3720 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4792 -0.5196 -0.5216 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7262 -1.7383 1.5931 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7455 -1.2995 2.9980 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8816 0.1360 2.7678 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6250 0.6790 1.4827 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1699 3.5764 -1.8841 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9544 4.2692 -3.2961 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8057 0.2856 -3.0128 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9710 -1.2091 -2.4186 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3554 -3.0680 -1.6331 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6766 -4.4259 0.2763 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5453 -3.9103 1.4357 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1316 -2.0161 0.6376 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3072 0.2822 0.5475 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2391 3.3375 2.1801 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2271 1.2829 3.1776 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6365 2.9055 3.9067 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4870 4.2888 1.7327 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4156 1.7231 2.0610 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9079 0.5255 3.7958 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5164 -2.6280 -0.3708 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2591 -3.4009 -2.0060 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5509 -0.8275 -2.8540 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9881 -3.1228 -1.9142 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6536 -0.1174 -2.1435 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9387 -1.2704 -0.7228 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 1 0 13 15 2 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 19 26 1 0 26 27 1 0 27 28 2 0 9 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 4 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 39 2 1 0 33 7 1 0 28 11 1 0 27 15 1 0 25 20 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 6 4 45 1 6 6 46 1 0 6 47 1 0 7 48 1 1 9 49 1 1 12 50 1 0 14 51 1 0 18 52 1 0 21 53 1 0 22 54 1 0 23 55 1 0 24 56 1 0 25 57 1 0 28 58 1 0 29 59 1 6 30 60 1 0 31 61 1 1 32 62 1 0 33 63 1 6 34 64 1 0 35 65 1 1 36 66 1 0 37 67 1 6 38 68 1 0 39 69 1 6 40 70 1 0 M END

Standard InCHIKey	QNFMEZGAYVOUCH-GDHGFZABSA-N
Standard InCHI	InChI=1S/C27H30O13/c1-11-20(30)22(32)24(34)26(37-11)36-10-18-21(31)23(33)25(35)27(40-18)38-13-7-14(28)19-15(29)9-16(39-17(19)8-13)12-5-3-2-4-6-12/h2-9,11,18,20-28,30-35H,10H2,1H3/t11-,18-,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1
SMILES	C[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=CC(O)=C4C(=O)C=C(C5=CC=CC=C5)OC4=C3)[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:	562.17	Volume:	525.947 ? Van der Waals volume.
Dense:	1.069	LogP:	0.919 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.301 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.555 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	208.74 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.196	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.522	Fsp³:	0.444
MCE-18:	112.41 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.622	Fluc inhibitor:	0.299 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.819 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.631 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.088	Promiscuous compounds:	0.262

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.416	MDCK Permeability:	-5.126
Pgp-inhibitor:	0.001	Pgp-substrate:	0.799
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):	0.182
20% Bioavailability (F20%):	0.057	30% Bioavailability (F30%):	0.939
50% Bioavailability (F50%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.177
Plasma Protein Binding (PPB):	90.821%	Volume Distribution (VD):	-0.176
Fu:	8.478% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.991
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.422
BSEP inhibitor:	0.543

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:	0.005
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.997
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.985
HLM stability:	0.024 ? 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):

1.063

Half-life (T1/2):

4.406

ADMET: Toxicity

hERG Blockers:	0.036	hERG Blockers (10um):	0.325
Human Hepatotoxicity (H-HT):	0.332	Drug-induced Liver Injury (DILI):	0.965
AMES Toxicity:	0.707	Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.041	Skin Sensitization:	0.713
Carcinogencity:	0.05	Eye Corrosion:	0.0
Eye Irritation:	0.332	Respiratory Toxicity:	0.009
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.856
Hematotoxicity:	0.052	Drug-induced Nephrotoxicity:	0.529
Genotoxicity:	0.212	RPMI-8226 Immunitoxicity:	0.152
A549 Cytotoxicity:	0.212	Hek293 Cytotoxicity:	0.229
BCF:	0.57 ? 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:	3.24 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.721 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.9 ? 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
NPO9023	Dolichandrone falcata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9023	Dolichandrone falcata	Species	Bignoniaceae	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 NPC591853 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	20405
0.1-0.2	25659
0.2-0.3	2832
0.3-0.4	590
0.4-0.5	234
0.5-0.6	89
0.6-0.7	32
0.7-0.8	0
0.8-0.85	1
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8861	High Similarity	NPC44931
0.875	High Similarity	NPC22062
0.875	High Similarity	NPC473634
0.875	High Similarity	NPC138811
0.8519	High Similarity	NPC210073
0.8118	Intermediate Similarity	NPC209296
0.7303	Intermediate Similarity	NPC473623
0.7253	Intermediate Similarity	NPC101636
0.7222	Intermediate Similarity	NPC488089
0.7159	Intermediate Similarity	NPC204693
0.7126	Intermediate Similarity	NPC67105
0.7126	Intermediate Similarity	NPC227508
0.7125	Intermediate Similarity	NPC331652
0.7021	Intermediate Similarity	NPC11468
0.6966	Remote Similarity	NPC186816
0.6829	Remote Similarity	NPC19709
0.6813	Remote Similarity	NPC65711
0.6707	Remote Similarity	NPC473043
0.6702	Remote Similarity	NPC298171
0.6633	Remote Similarity	NPC473644
0.6566	Remote Similarity	NPC311850
0.6522	Remote Similarity	NPC46202
0.6522	Remote Similarity	NPC64051
0.6458	Remote Similarity	NPC472994
0.6383	Remote Similarity	NPC229409
0.6373	Remote Similarity	NPC68592
0.6316	Remote Similarity	NPC270675
0.6316	Remote Similarity	NPC195685
0.6311	Remote Similarity	NPC298666
0.6304	Remote Similarity	NPC303913
0.6279	Remote Similarity	NPC181712
0.625	Remote Similarity	NPC475382
0.6235	Remote Similarity	NPC39360
0.6235	Remote Similarity	NPC29763
0.6235	Remote Similarity	NPC210003
0.6207	Remote Similarity	NPC27942
0.6196	Remote Similarity	NPC275454
0.617	Remote Similarity	NPC475366
0.6163	Remote Similarity	NPC95090
0.6163	Remote Similarity	NPC27408
0.6154	Remote Similarity	NPC198199
0.6129	Remote Similarity	NPC65003
0.6111	Remote Similarity	NPC190003
0.6058	Remote Similarity	NPC488086
0.6019	Remote Similarity	NPC262222
0.6019	Remote Similarity	NPC488087
0.5981	Remote Similarity	NPC120952
0.5977	Remote Similarity	NPC189142
0.5977	Remote Similarity	NPC77660
0.5914	Remote Similarity	NPC187379
0.5895	Remote Similarity	NPC115674
0.5882	Remote Similarity	NPC472993
0.5876	Remote Similarity	NPC483707
0.587	Remote Similarity	NPC211594
0.5865	Remote Similarity	NPC488083
0.5862	Remote Similarity	NPC261866
0.5825	Remote Similarity	NPC480441
0.5825	Remote Similarity	NPC25523
0.5789	Remote Similarity	NPC473512
0.5789	Remote Similarity	NPC129827
0.5714	Remote Similarity	NPC22832
0.5714	Remote Similarity	NPC243930
0.5714	Remote Similarity	NPC601144
0.5699	Remote Similarity	NPC172807
0.5684	Remote Similarity	NPC173582
0.5684	Remote Similarity	NPC265885
0.5684	Remote Similarity	NPC181465
0.5684	Remote Similarity	NPC215710
0.5684	Remote Similarity	NPC473438
0.5684	Remote Similarity	NPC253788
0.5682	Remote Similarity	NPC108831
0.5682	Remote Similarity	NPC238376
0.5682	Remote Similarity	NPC182634
0.5658	Remote Similarity	NPC127447
0.5657	Remote Similarity	NPC142142
0.5652	Remote Similarity	NPC311830
0.5652	Remote Similarity	NPC607707
0.5644	Remote Similarity	NPC135358
0.5625	Remote Similarity	NPC203259
0.5625	Remote Similarity	NPC33054
0.5625	Remote Similarity	NPC176740
0.5625	Remote Similarity	NPC471725
0.5625	Remote Similarity	NPC134532
0.5625	Remote Similarity	NPC602582
0.5612	Remote Similarity	NPC470443
0.56	Remote Similarity	NPC195257
0.5579	Remote Similarity	NPC295613
0.5579	Remote Similarity	NPC473657
0.5521	Remote Similarity	NPC39834
0.5506	Remote Similarity	NPC249281
0.5506	Remote Similarity	NPC45618
0.5474	Remote Similarity	NPC254540
0.5464	Remote Similarity	NPC479405
0.5464	Remote Similarity	NPC65563
0.5464	Remote Similarity	NPC470949
0.5446	Remote Similarity	NPC473073
0.5426	Remote Similarity	NPC276377
0.5408	Remote Similarity	NPC479404
0.5408	Remote Similarity	NPC473571
0.5408	Remote Similarity	NPC110941
0.54	Remote Similarity	NPC473327
0.5385	Remote Similarity	NPC46420
0.5385	Remote Similarity	NPC271692
0.5376	Remote Similarity	NPC181616
0.537	Remote Similarity	NPC488088
0.5354	Remote Similarity	NPC126784
0.5354	Remote Similarity	NPC241423
0.5319	Remote Similarity	NPC99957
0.5312	Remote Similarity	NPC8856
0.53	Remote Similarity	NPC479403
0.5294	Remote Similarity	NPC476472
0.5294	Remote Similarity	NPC294815
0.5294	Remote Similarity	NPC16194
0.5275	Remote Similarity	NPC158674
0.5269	Remote Similarity	NPC611303
0.5213	Remote Similarity	NPC80188
0.5204	Remote Similarity	NPC15358
0.52	Remote Similarity	NPC284277
0.52	Remote Similarity	NPC475497
0.5196	Remote Similarity	NPC479766
0.5192	Remote Similarity	NPC179862
0.5158	Remote Similarity	NPC116458
0.5158	Remote Similarity	NPC246943
0.5158	Remote Similarity	NPC220169
0.5158	Remote Similarity	NPC605784
0.5152	Remote Similarity	NPC150164
0.5146	Remote Similarity	NPC80068
0.5146	Remote Similarity	NPC479765
0.5146	Remote Similarity	NPC477629
0.5143	Remote Similarity	NPC14187
0.5106	Remote Similarity	NPC282169
0.5098	Remote Similarity	NPC32641
0.5098	Remote Similarity	NPC256188
0.5054	Remote Similarity	NPC472385
0.5053	Remote Similarity	NPC608742

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC591853 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4727
0.1-0.2	4333
0.2-0.3	77
0.3-0.4	7
0.4-0.5	1
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
0.8118	Intermediate Similarity	NPD7054	Phase 4
0.6421	Remote Similarity	NPD7251	Phase 2
0.6162	Remote Similarity	NPD7808	Phase 3
0.6	Remote Similarity	NPD7472	Pre-clinical
0.5625	Remote Similarity	NPD6797	Phase 2

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