NPASS Compound

Natural Product: NPC135021

Natural Product ID	NPC135021
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BXWABJPTCUDBMM-UDGCLMCYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11331595
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 83 89 0 0 0 0 0 0 0 0999 V2000 4.0089 1.9396 1.9926 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7198 3.1175 1.7536 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3175 3.3405 0.5338 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1970 2.3763 -0.4418 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4857 1.2084 -0.1884 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8843 0.9716 1.0231 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1403 -0.2564 1.3129 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0855 -1.4465 1.5181 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2946 -2.5619 2.1463 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0495 -2.7871 1.3664 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3798 -3.9858 1.5396 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2180 -4.2016 0.8200 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2733 -3.2544 -0.0524 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3866 -2.0613 -0.2293 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1284 -1.0473 -1.1505 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9293 -0.4771 -2.0302 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5870 -1.2507 -2.9692 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5647 -0.7116 -3.7746 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8973 0.6143 -3.6489 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2306 1.3699 -2.7073 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2382 0.8631 -1.8761 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5649 1.6280 -0.9257 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8162 1.3775 -0.7730 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3892 2.1465 0.3626 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5749 2.8269 0.2130 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1491 3.5549 1.2404 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5264 3.6079 2.4512 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3199 2.9298 2.6427 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7748 2.2140 1.5992 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6849 2.9830 3.8748 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0541 4.3195 3.5132 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0790 -0.0808 -0.5704 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4257 -0.2917 -0.9591 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4630 -0.6567 -0.1481 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1930 -0.8258 1.0758 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8184 -0.8437 -0.6648 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1375 -0.6590 -1.9898 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3964 -0.8228 -2.4984 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4259 -1.1964 -1.6493 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1343 -1.3909 -0.3044 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8400 -1.2157 0.1837 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1491 -1.7647 0.5594 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6904 -1.3603 -2.1618 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7066 -0.6325 -3.8402 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8814 1.1530 -4.4608 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2206 -2.6036 -3.0697 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5448 -1.8320 0.4795 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2220 -0.6367 0.3111 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4191 -3.4702 -0.7604 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8958 -4.9212 2.4235 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1289 -1.0449 2.3243 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7970 2.5947 -1.6737 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0312 4.5224 0.2950 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5453 1.7968 2.9780 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8227 3.8822 2.5086 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3922 0.4602 -0.9439 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5769 -0.1804 2.2763 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4304 -1.7283 0.4984 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1109 -2.4180 3.2129 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9052 -3.5045 2.0244 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3076 -5.1421 0.9547 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7513 -1.6562 -1.9081 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0764 -1.3014 -4.5019 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4847 2.4186 -2.5963 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3764 1.7023 -1.7024 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1271 2.8308 -0.7225 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0888 4.0912 1.1117 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1564 1.6960 1.7623 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7773 2.1577 4.4885 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0751 4.4589 3.5691 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0868 -0.2690 0.5496 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3422 -0.3685 -2.6557 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6014 -1.3652 1.2299 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1015 -1.7992 0.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8723 -1.6765 -3.1033 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4213 -1.2832 -4.5439 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0122 2.1736 -4.4506 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7553 -2.9541 -3.8974 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2772 -3.6426 -0.2489 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9325 -5.9106 2.2404 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0131 -1.3104 1.9993 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7178 2.9829 -1.7890 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9428 4.4908 -0.1862 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 27 31 1 0 23 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 40 42 1 0 39 43 1 0 38 44 1 0 19 45 1 0 17 46 1 0 14 47 2 0 47 48 1 0 13 49 1 0 11 50 1 0 8 51 1 0 4 52 1 0 3 53 1 0 6 1 1 0 48 7 1 0 47 10 1 0 32 15 1 0 41 36 1 0 21 16 1 0 29 24 1 0 1 54 1 0 2 55 1 0 5 56 1 0 7 57 1 1 8 58 1 6 9 59 1 0 9 60 1 0 12 61 1 0 15 62 1 6 18 63 1 0 20 64 1 0 23 65 1 6 25 66 1 0 26 67 1 0 29 68 1 0 30 69 1 0 31 70 1 0 32 71 1 1 37 72 1 0 41 73 1 0 42 74 1 0 43 75 1 0 44 76 1 0 45 77 1 0 46 78 1 0 49 79 1 0 50 80 1 0 51 81 1 0 52 82 1 0 53 83 1 0 M END

Standard InCHIKey	BXWABJPTCUDBMM-UDGCLMCYSA-N
Standard InCHI	InChI=1S/C37H30O16/c38-16-9-23(44)29-28(10-16)51-34(14-2-4-19(40)22(43)6-14)36(53-37(50)15-7-25(46)32(49)26(47)8-15)31(29)30-24(45)12-20(41)17-11-27(48)33(52-35(17)30)13-1-3-18(39)21(42)5-13/h1-10,12,27,31,33-34,36,38-49H,11H2/t27-,31-,33+,34+,36-/m0/s1
SMILES	c1cc(c(cc1[C@@H]1[C@H](Cc2c(cc(c([C@@H]3c4c(cc(cc4O[C@H](c4ccc(c(c4)O)O)[C@H]3OC(=O)c3cc(c(c(c3)O)O)O)O)O)c2O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	730.15	Volume:	687.073 ? Van der Waals volume.
Dense:	1.063	LogP:	1.554 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.618 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.054 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	41.0
TPSA:	287.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	12.0	Rings:	7.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.09	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.854	Fsp³:	0.162
MCE-18:	150.837 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.947	Fluc inhibitor:	0.197 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.483 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.622 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.591	Promiscuous compounds:	0.521

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.429	MDCK Permeability:	-4.802
Pgp-inhibitor:	0.0	Pgp-substrate:	0.046
PAMPA:	0.365 ? 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):	0.002
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.997
Plasma Protein Binding (PPB):	90.265%	Volume Distribution (VD):	-0.071
Fu:	11.815% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.447
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.012	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

5.246

Half-life (T1/2):

4.815

ADMET: Toxicity

hERG Blockers:	0.134	hERG Blockers (10um):	0.957
Human Hepatotoxicity (H-HT):	0.536	Drug-induced Liver Injury (DILI):	0.863
AMES Toxicity:	0.329	Rat Oral Acute Toxicity:	0.214
Maximum Recommended Daily Dose:	0.982	Skin Sensitization:	1.0
Carcinogencity:	0.016	Eye Corrosion:	0.0
Eye Irritation:	0.93	Respiratory Toxicity:	0.557
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.997
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.003
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.002
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.958
BCF:	0.981 ? 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:	3.703 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.923 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.34 ? 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
NPO40956	Woodfordia uniflora	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[32639158]

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

Activity Type	# Activity
MIC	3

Activity Type	# Activity
Organism	3

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
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	17100.0	nM	PMID[32639158]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	4200.0	nM	PMID[32639158]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	8500.0	nM	PMID[32639158]

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 NPC135021 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	20015
0.1-0.2	26258
0.2-0.3	3224
0.3-0.4	210
0.4-0.5	57
0.5-0.6	62
0.6-0.7	27
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
0.7838	Intermediate Similarity	NPC98583
0.6933	Remote Similarity	NPC100251
0.65	Remote Similarity	NPC20050
0.6486	Remote Similarity	NPC58190
0.6486	Remote Similarity	NPC108811
0.6486	Remote Similarity	NPC170103
0.6486	Remote Similarity	NPC236202
0.6486	Remote Similarity	NPC262911
0.6486	Remote Similarity	NPC202742
0.6456	Remote Similarity	NPC302549
0.642	Remote Similarity	NPC306267
0.64	Remote Similarity	NPC246202
0.64	Remote Similarity	NPC224161
0.64	Remote Similarity	NPC46335
0.64	Remote Similarity	NPC279406
0.64	Remote Similarity	NPC486519
0.6329	Remote Similarity	NPC600630
0.6329	Remote Similarity	NPC607896
0.6329	Remote Similarity	NPC611369
0.6081	Remote Similarity	NPC38779
0.6081	Remote Similarity	NPC114179
0.6081	Remote Similarity	NPC68324
0.6081	Remote Similarity	NPC289322
0.6081	Remote Similarity	NPC160512
0.6049	Remote Similarity	NPC278548
0.6026	Remote Similarity	NPC313116
0.6026	Remote Similarity	NPC603340
0.6	Remote Similarity	NPC96576
0.5976	Remote Similarity	NPC44192
0.5875	Remote Similarity	NPC70409
0.5875	Remote Similarity	NPC204770
0.5875	Remote Similarity	NPC600551
0.5875	Remote Similarity	NPC601980
0.5875	Remote Similarity	NPC602065
0.5875	Remote Similarity	NPC611024
0.5854	Remote Similarity	NPC65333
0.5802	Remote Similarity	NPC601997
0.5802	Remote Similarity	NPC609211
0.5802	Remote Similarity	NPC610665
0.573	Remote Similarity	NPC106601
0.573	Remote Similarity	NPC151474
0.5667	Remote Similarity	NPC212614
0.5667	Remote Similarity	NPC205613
0.5618	Remote Similarity	NPC86630
0.5571	Remote Similarity	NPC261619
0.5571	Remote Similarity	NPC61477
0.5571	Remote Similarity	NPC78770
0.5571	Remote Similarity	NPC219876
0.5571	Remote Similarity	NPC126029
0.5571	Remote Similarity	NPC15658
0.5568	Remote Similarity	NPC147743
0.5568	Remote Similarity	NPC4809
0.5568	Remote Similarity	NPC73517
0.5542	Remote Similarity	NPC272552
0.5542	Remote Similarity	NPC226108
0.5542	Remote Similarity	NPC322899
0.55	Remote Similarity	NPC184245
0.55	Remote Similarity	NPC187801
0.55	Remote Similarity	NPC610920
0.5476	Remote Similarity	NPC46283
0.5476	Remote Similarity	NPC469944
0.5465	Remote Similarity	NPC478616
0.5465	Remote Similarity	NPC478339
0.5455	Remote Similarity	NPC156818
0.5443	Remote Similarity	NPC277331
0.5443	Remote Similarity	NPC100482
0.5422	Remote Similarity	NPC226809
0.5375	Remote Similarity	NPC294558
0.5375	Remote Similarity	NPC18185
0.5375	Remote Similarity	NPC263940
0.525	Remote Similarity	NPC9636
0.525	Remote Similarity	NPC601196
0.525	Remote Similarity	NPC601999
0.5238	Remote Similarity	NPC211561
0.52	Remote Similarity	NPC291948
0.52	Remote Similarity	NPC104983
0.52	Remote Similarity	NPC250436
0.52	Remote Similarity	NPC300845
0.52	Remote Similarity	NPC88803
0.5158	Remote Similarity	NPC159526
0.5122	Remote Similarity	NPC165483
0.5116	Remote Similarity	NPC134911
0.507	Remote Similarity	NPC268266
0.507	Remote Similarity	NPC42760
0.507	Remote Similarity	NPC220825
0.507	Remote Similarity	NPC268342
0.5063	Remote Similarity	NPC474656
0.506	Remote Similarity	NPC308402
0.5054	Remote Similarity	NPC78074
0.5052	Remote Similarity	NPC478617

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC135021 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4402
0.1-0.2	4697
0.2-0.3	42
0.3-0.4	5
0.4-0.5	1
0.5-0.6	3
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
0.5571	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5571	Remote Similarity	NPD1613	Phase 4
0.52	Remote Similarity	NPD4868	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