NPASS Compound

Natural Product: NPC276325

Natural Product ID	NPC276325
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XKBXVZQCIOLGJN-VQKKVCIBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11650625
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 85 91 0 0 0 0 0 0 0 0999 V2000 5.5413 -3.4412 4.4963 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8601 -4.0546 3.2421 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5704 -3.3700 2.0634 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8482 -3.8944 0.8225 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5516 -3.1943 -0.3601 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9726 -1.9601 -0.3053 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6929 -1.4334 0.9491 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9845 -2.1207 2.1069 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6489 -1.1803 -1.5207 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9158 -1.6273 -2.7903 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5815 -0.8315 -3.8851 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8233 -1.2355 -5.0381 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9884 0.3856 -3.6225 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6258 1.2358 -4.6450 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0324 2.4579 -4.4130 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7811 2.8685 -3.1199 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1358 2.0328 -2.0877 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8765 2.4291 -0.7257 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6737 2.0958 -0.1384 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3758 2.4588 1.1805 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3290 3.1607 1.8674 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5506 3.4979 1.2667 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8255 3.1324 -0.0305 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0646 3.4918 -0.5951 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0096 4.2253 0.1856 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0869 2.0835 1.7510 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2046 2.4367 3.0364 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4256 2.0868 3.5900 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7348 2.3881 4.7589 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3117 1.3875 2.8147 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5329 1.0381 3.3669 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4285 0.3446 2.6163 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1155 -0.0124 1.2953 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8986 0.3487 0.7791 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9586 1.0648 1.5352 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7970 1.4109 1.0442 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0815 -0.7047 0.6300 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9660 -1.1692 -0.6691 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1856 -2.6714 -0.7536 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5273 -3.0059 -0.1398 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4692 -1.8508 -0.4132 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0678 -1.0969 -1.6641 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0769 0.0433 -1.8307 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3712 -0.4045 -1.9497 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8312 -0.5092 -1.5563 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7788 -2.2795 -0.5789 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4212 -3.1168 1.2593 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1460 -3.0233 -2.0960 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8260 1.3992 4.6758 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7308 0.8096 -2.3310 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0825 -0.0092 -1.3755 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1733 4.1199 -2.8740 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8726 0.8350 -5.9429 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8707 -4.0446 5.3407 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0938 -2.4584 4.4815 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4782 -3.1770 4.4787 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3074 -4.8723 0.7336 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7863 -3.6440 -1.3211 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2340 -0.4539 0.9719 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7654 -1.7078 3.0939 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3847 -2.5973 -2.9379 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7456 3.1312 -5.2137 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 1.5415 -0.6542 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1809 3.4758 2.8751 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2915 4.0579 1.8418 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9237 4.4011 -0.3800 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5478 5.1256 0.6199 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2685 3.5669 1.0587 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4558 2.9903 3.7004 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3828 0.0754 3.0588 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6059 0.1016 -0.2306 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9555 -0.9930 -1.0637 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3872 -3.1714 -0.2063 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8804 -3.9655 -0.5159 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3716 -1.1171 0.4279 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1244 -1.8107 -2.5059 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7604 0.6763 -2.6933 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0042 0.6870 -0.9311 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8396 -0.0979 -2.7663 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3552 -1.7123 0.0023 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2889 -3.2112 1.6814 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3565 -3.9980 -2.1751 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5972 2.0394 4.8792 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1796 4.1577 -3.0241 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4463 1.4742 -6.5083 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 6 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 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 1 0 20 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 33 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 42 45 1 0 41 46 1 0 40 47 1 0 39 48 1 0 31 49 1 0 17 50 2 0 50 51 1 0 16 52 1 0 14 53 1 0 8 3 1 0 51 9 1 0 50 13 1 0 23 18 1 0 36 26 1 0 45 38 1 0 35 30 1 0 1 54 1 0 1 55 1 0 1 56 1 0 4 57 1 0 5 58 1 0 7 59 1 0 8 60 1 0 10 61 1 0 15 62 1 0 19 63 1 0 21 64 1 0 22 65 1 0 25 66 1 0 25 67 1 0 25 68 1 0 27 69 1 0 32 70 1 0 34 71 1 0 38 72 1 6 39 73 1 1 40 74 1 6 41 75 1 1 42 76 1 6 43 77 1 0 43 78 1 0 44 79 1 0 46 80 1 0 47 81 1 0 48 82 1 0 49 83 1 0 52 84 1 0 53 85 1 0 M END

Standard InCHIKey	XKBXVZQCIOLGJN-VQKKVCIBSA-N
Standard InCHI	InChI=1S/C38H32O15/c1-48-18-6-3-16(4-7-18)27-14-25(44)33-23(42)12-22(41)31(37(33)52-27)20-9-17(5-8-26(20)49-2)28-13-24(43)32-21(40)10-19(11-29(32)51-28)50-38-36(47)35(46)34(45)30(15-39)53-38/h3-14,30,34-36,38-42,45-47H,15H2,1-2H3/t30-,34-,35+,36-,38-/m1/s1
SMILES	COc1ccc(cc1)c1cc(=O)c2c(cc(c(c3cc(ccc3OC)c3cc(=O)c4c(cc(cc4o3)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O)c2o1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	728.17	Volume:	695.579 ? Van der Waals volume.
Dense:	1.047	LogP:	2.976 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.114 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.514 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	42.0
TPSA:	238.95 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.119	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.497	Fsp³:	0.211
MCE-18:	141.565 ? 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:	0.724	Fluc inhibitor:	0.294 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.99 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.999 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.093	Promiscuous compounds:	0.782

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.077	MDCK Permeability:	-5.336
Pgp-inhibitor:	0.003	Pgp-substrate:	0.784
PAMPA:	0.934 ? 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):	0.543
20% Bioavailability (F20%):	0.197	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.679
Plasma Protein Binding (PPB):	97.11%	Volume Distribution (VD):	-0.096
Fu:	2.999% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.885
BSEP inhibitor:	0.206

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.105	CYP2D6-substrate:	0.039
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.075 ? 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):

1.46

Half-life (T1/2):

4.181

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.104
Human Hepatotoxicity (H-HT):	0.667	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.969	Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.482	Skin Sensitization:	0.932
Carcinogencity:	0.686	Eye Corrosion:	0.0
Eye Irritation:	0.228	Respiratory Toxicity:	0.139
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.693
Hematotoxicity:	0.151	Drug-induced Nephrotoxicity:	0.36
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.242
A549 Cytotoxicity:	0.641	Hek293 Cytotoxicity:	0.83
BCF:	0.969 ? 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:	3.954 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.021 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.565 ? 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
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	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 NPC276325 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	24162
0.1-0.2	22285
0.2-0.3	2354
0.3-0.4	701
0.4-0.5	232
0.5-0.6	87
0.6-0.7	29
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
0.7927	Intermediate Similarity	NPC95090
0.7927	Intermediate Similarity	NPC27408
0.747	Intermediate Similarity	NPC14606
0.6966	Remote Similarity	NPC22832
0.6966	Remote Similarity	NPC243930
0.6818	Remote Similarity	NPC181712
0.6818	Remote Similarity	NPC265624
0.6782	Remote Similarity	NPC39360
0.6782	Remote Similarity	NPC29763
0.6782	Remote Similarity	NPC210003
0.6703	Remote Similarity	NPC607707
0.6591	Remote Similarity	NPC261866
0.6591	Remote Similarity	NPC143851
0.6522	Remote Similarity	NPC311830
0.6517	Remote Similarity	NPC189142
0.6517	Remote Similarity	NPC77660
0.6444	Remote Similarity	NPC186807
0.6437	Remote Similarity	NPC150908
0.6404	Remote Similarity	NPC58053
0.6289	Remote Similarity	NPC22062
0.6289	Remote Similarity	NPC473634
0.6289	Remote Similarity	NPC138811
0.6237	Remote Similarity	NPC80188
0.6237	Remote Similarity	NPC601144
0.6222	Remote Similarity	NPC121649
0.6078	Remote Similarity	NPC475382
0.604	Remote Similarity	NPC473623
0.6022	Remote Similarity	NPC27942
0.6	Remote Similarity	NPC88023
0.6	Remote Similarity	NPC46202
0.6	Remote Similarity	NPC220169
0.6	Remote Similarity	NPC309025
0.598	Remote Similarity	NPC488089
0.5955	Remote Similarity	NPC248739
0.5926	Remote Similarity	NPC311850
0.5872	Remote Similarity	NPC488083
0.587	Remote Similarity	NPC289667
0.5824	Remote Similarity	NPC71061
0.5806	Remote Similarity	NPC18699
0.5789	Remote Similarity	NPC191306
0.5766	Remote Similarity	NPC68592
0.5761	Remote Similarity	NPC331652
0.5729	Remote Similarity	NPC486578
0.5657	Remote Similarity	NPC8856
0.5638	Remote Similarity	NPC93337
0.5638	Remote Similarity	NPC323593
0.5638	Remote Similarity	NPC203500
0.5625	Remote Similarity	NPC285197
0.5625	Remote Similarity	NPC609451
0.5591	Remote Similarity	NPC194593
0.5591	Remote Similarity	NPC186227
0.5579	Remote Similarity	NPC84362
0.5579	Remote Similarity	NPC105025
0.5577	Remote Similarity	NPC209296
0.5567	Remote Similarity	NPC605067
0.5567	Remote Similarity	NPC608742
0.5532	Remote Similarity	NPC19709
0.5521	Remote Similarity	NPC472459
0.549	Remote Similarity	NPC65003
0.5474	Remote Similarity	NPC277205
0.5474	Remote Similarity	NPC37919
0.547	Remote Similarity	NPC262222
0.5464	Remote Similarity	NPC307938
0.5455	Remote Similarity	NPC190003
0.5426	Remote Similarity	NPC159707
0.5426	Remote Similarity	NPC473043
0.5417	Remote Similarity	NPC45638
0.5417	Remote Similarity	NPC610763
0.5413	Remote Similarity	NPC11468
0.5408	Remote Similarity	NPC601710
0.5392	Remote Similarity	NPC44931
0.5368	Remote Similarity	NPC45618
0.5361	Remote Similarity	NPC201292
0.5327	Remote Similarity	NPC195257
0.5319	Remote Similarity	NPC303485
0.5319	Remote Similarity	NPC158027
0.5312	Remote Similarity	NPC205026
0.5312	Remote Similarity	NPC297987
0.5312	Remote Similarity	NPC146792
0.5312	Remote Similarity	NPC136042
0.5312	Remote Similarity	NPC234739
0.5306	Remote Similarity	NPC55443
0.5304	Remote Similarity	NPC198199
0.5301	Remote Similarity	NPC29353
0.53	Remote Similarity	NPC601586
0.5294	Remote Similarity	NPC603300
0.5288	Remote Similarity	NPC115674
0.5283	Remote Similarity	NPC124155
0.5268	Remote Similarity	NPC473644
0.5258	Remote Similarity	NPC73511
0.5248	Remote Similarity	NPC211594
0.5238	Remote Similarity	NPC64051
0.5229	Remote Similarity	NPC135358
0.5204	Remote Similarity	NPC182045
0.5204	Remote Similarity	NPC60966
0.52	Remote Similarity	NPC602805
0.5196	Remote Similarity	NPC251417
0.5192	Remote Similarity	NPC210073
0.5175	Remote Similarity	NPC488087
0.5172	Remote Similarity	NPC298666
0.5169	Remote Similarity	NPC120952
0.5155	Remote Similarity	NPC64305
0.5155	Remote Similarity	NPC168822
0.5143	Remote Similarity	NPC204693
0.514	Remote Similarity	NPC229409
0.5109	Remote Similarity	NPC191154
0.5102	Remote Similarity	NPC58716
0.51	Remote Similarity	NPC284960
0.5093	Remote Similarity	NPC479766
0.5093	Remote Similarity	NPC270675
0.5093	Remote Similarity	NPC195685
0.5054	Remote Similarity	NPC134819
0.5052	Remote Similarity	NPC83283
0.5052	Remote Similarity	NPC215203
0.505	Remote Similarity	NPC116458
0.505	Remote Similarity	NPC246943
0.505	Remote Similarity	NPC605784
0.5047	Remote Similarity	NPC65711
0.5044	Remote Similarity	NPC472993

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC276325 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5808
0.1-0.2	3286
0.2-0.3	40
0.3-0.4	10
0.4-0.5	5
0.5-0.6	1
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
0.5577	Remote Similarity	NPD7054	Phase 4

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