NPASS Compound

Natural Product: NPC306863

Natural Product ID	NPC306863
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MYHQIVSWYXBWOC-VMPREFPWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10393930
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0002463] Diarylethers

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 5.3010 1.3293 3.3071 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1901 0.1878 2.3996 N 0 0 0 0 0 0 0 0 0 0 0 0 5.6405 -0.9566 3.1543 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4524 -2.2425 2.4642 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5482 -2.1722 1.3070 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5744 -3.2467 0.4039 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7236 -3.1859 -0.6730 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8742 -2.1177 -0.8673 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8810 -1.0926 0.0338 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7009 -1.1058 1.1115 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7685 -0.0296 2.1474 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0917 1.2358 1.7700 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6312 1.2048 1.6498 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9025 0.2538 2.2866 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4824 0.2562 2.1330 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1086 1.1859 1.3638 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3600 2.1436 0.7250 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0259 2.1514 0.8713 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4674 1.1811 1.2168 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1723 2.0791 0.4328 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6776 1.8490 -0.8062 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3559 2.8708 -1.4337 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9306 2.5465 -2.7891 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5840 1.1721 -2.5466 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5700 0.2073 -2.3794 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2704 -0.4368 -3.6072 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5097 0.5218 -1.4964 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2029 0.4083 -2.1836 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4258 -0.7953 -1.8329 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0427 -1.8825 -1.2627 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3398 -3.0411 -0.9136 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0134 -3.1001 -1.1487 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6197 -1.9970 -1.7272 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0624 -0.8667 -2.0659 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0103 -2.0764 -1.9691 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7476 -4.2169 -0.8190 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2221 -5.3734 -0.2281 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5515 4.1088 -0.8834 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0417 4.3646 0.3844 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3683 3.3504 1.0090 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8452 3.5923 2.2963 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1729 5.5625 1.0389 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8056 6.7156 0.6086 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6807 -4.2078 -1.6267 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5014 -5.3531 -1.5364 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4527 1.2725 4.0056 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2396 1.1893 3.8951 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3816 2.2879 2.7930 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0336 -0.9608 4.0977 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6999 -0.8054 3.5000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4517 -2.6269 2.1052 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0666 -3.0092 3.1746 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2275 -4.0899 0.5415 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2217 -0.2706 -0.1541 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3601 -0.3904 3.1128 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5769 1.5679 0.7944 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3762 2.0375 2.4920 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3773 -0.5010 2.9034 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0555 -0.4986 2.6363 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8594 2.8951 0.1046 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5643 2.9293 0.3441 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7625 3.2200 -3.0619 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1789 2.5306 -3.5703 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1741 1.2756 -1.6061 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3062 0.9452 -3.3385 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0312 0.2547 -4.4501 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2403 -0.9302 -3.9436 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5635 -1.2820 -3.5752 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5730 -0.1972 -0.6236 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3678 0.3253 -3.3041 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5813 1.3372 -2.1104 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1143 -1.9326 -1.0589 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8999 -3.8530 -0.4684 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4682 -0.0417 -2.5060 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0043 -6.1997 -0.9429 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6553 -5.1314 0.3966 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9988 -5.7692 0.4925 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0787 4.9101 -1.3690 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0855 4.2860 2.3214 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5385 6.9528 -0.4256 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9022 6.7335 0.7918 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3994 7.5568 1.2440 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5599 -5.0706 -1.4319 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3698 -5.9438 -2.4640 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1831 -5.9851 -0.6608 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 16 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 33 35 1 0 32 36 1 0 36 37 1 0 22 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 39 42 1 0 42 43 1 0 7 44 1 0 44 45 1 0 11 2 1 0 18 13 1 0 40 20 1 0 10 5 1 0 27 21 1 0 34 29 1 0 35 8 1 0 1 46 1 0 1 47 1 0 1 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 6 53 1 0 9 54 1 0 11 55 1 1 12 56 1 0 12 57 1 0 14 58 1 0 15 59 1 0 17 60 1 0 18 61 1 0 23 62 1 0 23 63 1 0 24 64 1 0 24 65 1 0 26 66 1 0 26 67 1 0 26 68 1 0 27 69 1 1 28 70 1 0 28 71 1 0 30 72 1 0 31 73 1 0 34 74 1 0 37 75 1 0 37 76 1 0 37 77 1 0 38 78 1 0 41 79 1 0 43 80 1 0 43 81 1 0 43 82 1 0 45 83 1 0 45 84 1 0 45 85 1 0 M END

Standard InCHIKey	MYHQIVSWYXBWOC-VMPREFPWSA-N
Standard InCHI	InChI=1S/C37H40N2O6/c1-38-14-12-24-19-31(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-37-35-25(20-34(43-5)36(37)40)13-15-39(2)29(35)17-23-8-11-30(41-3)32(18-23)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3/t28-,29-/m0/s1
SMILES	CN1CCc2cc(c3cc2[C@@H]1Cc1ccc(cc1)Oc1c2c(CCN(C)[C@H]2Cc2ccc(c(c2)O3)OC)cc(c1O)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	608.29	Volume:	631.71 ? Van der Waals volume.
Dense:	0.963	LogP:	3.407 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.005 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.278 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	42.0
TPSA:	72.86 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	1.0	Rings:	8.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.271	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.746	Fsp³:	0.351
MCE-18:	129.48 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.996	Fluc inhibitor:	0.194 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.7 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.936 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.224

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.963	MDCK Permeability:	-4.776
Pgp-inhibitor:	0.753	Pgp-substrate:	0.615
PAMPA:	0.004 ? 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):	0.001
20% Bioavailability (F20%):	0.341	30% Bioavailability (F30%):	0.601
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.921	MRP1:	0.967
Plasma Protein Binding (PPB):	73.944%	Volume Distribution (VD):	-0.172
Fu:	27.152% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.979
OATP1B3 inhibitor:	0.972	BCRP inhibitor:	0.848
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.056
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	0.024
HLM stability:	0.43 ? 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):

5.81

Half-life (T1/2):

3.322

ADMET: Toxicity

hERG Blockers:	0.81	hERG Blockers (10um):	0.812
Human Hepatotoxicity (H-HT):	0.56	Drug-induced Liver Injury (DILI):	0.009
AMES Toxicity:	0.668	Rat Oral Acute Toxicity:	0.626
Maximum Recommended Daily Dose:	0.954	Skin Sensitization:	0.663
Carcinogencity:	0.794	Eye Corrosion:	0.0
Eye Irritation:	0.01	Respiratory Toxicity:	0.785
Drug-induced Neurotoxicity:	0.827	Ototoxicity:	0.505
Hematotoxicity:	0.079	Drug-induced Nephrotoxicity:	0.261
Genotoxicity:	0.304	RPMI-8226 Immunitoxicity:	0.076
A549 Cytotoxicity:	0.147	Hek293 Cytotoxicity:	0.628
BCF:	1.891 ? 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:	4.405 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.748 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.131 ? 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
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19719093]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22512738]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13978	Cissampelos pareira	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13978	Cissampelos pareira	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13978	Cissampelos pareira	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13978	Cissampelos pareira	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13978	Cissampelos pareira	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13978	Cissampelos pareira	Species	Menispermaceae	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 NPC306863 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	28970
0.1-0.2	19507
0.2-0.3	1107
0.3-0.4	132
0.4-0.5	30
0.5-0.6	47
0.6-0.7	27
0.7-0.8	3
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC279228
0.9552	High Similarity	NPC290582
0.9552	High Similarity	NPC217748
0.9552	High Similarity	NPC182052
0.9552	High Similarity	NPC271013
0.9552	High Similarity	NPC42663
0.9552	High Similarity	NPC15414
0.8378	Intermediate Similarity	NPC290005
0.8133	Intermediate Similarity	NPC181796
0.8133	Intermediate Similarity	NPC54654
0.8133	Intermediate Similarity	NPC7715
0.8133	Intermediate Similarity	NPC328155
0.8133	Intermediate Similarity	NPC222661
0.8133	Intermediate Similarity	NPC285931
0.7763	Intermediate Similarity	NPC229373
0.7746	Intermediate Similarity	NPC76682
0.7746	Intermediate Similarity	NPC10908
0.7746	Intermediate Similarity	NPC63646
0.7746	Intermediate Similarity	NPC317145
0.7746	Intermediate Similarity	NPC198498
0.7746	Intermediate Similarity	NPC115284
0.7733	Intermediate Similarity	NPC311973
0.7727	Intermediate Similarity	NPC104196
0.75	Intermediate Similarity	NPC239824
0.7403	Intermediate Similarity	NPC116465
0.7397	Intermediate Similarity	NPC276890
0.7297	Intermediate Similarity	NPC603603
0.7237	Intermediate Similarity	NPC73492
0.7237	Intermediate Similarity	NPC299990
0.7206	Intermediate Similarity	NPC247639
0.7206	Intermediate Similarity	NPC25084
0.72	Intermediate Similarity	NPC12424
0.72	Intermediate Similarity	NPC129518
0.72	Intermediate Similarity	NPC251580
0.7179	Intermediate Similarity	NPC254441
0.7105	Intermediate Similarity	NPC603853
0.7024	Intermediate Similarity	NPC11296
0.7024	Intermediate Similarity	NPC274661
0.7013	Intermediate Similarity	NPC480587
0.6962	Remote Similarity	NPC185639
0.6962	Remote Similarity	NPC251735
0.6962	Remote Similarity	NPC49075
0.6962	Remote Similarity	NPC599951
0.6951	Remote Similarity	NPC275680
0.6951	Remote Similarity	NPC22115
0.6824	Remote Similarity	NPC82457
0.675	Remote Similarity	NPC223690
0.675	Remote Similarity	NPC9532
0.6548	Remote Similarity	NPC24260
0.6548	Remote Similarity	NPC8836
0.6429	Remote Similarity	NPC212237
0.642	Remote Similarity	NPC286119
0.641	Remote Similarity	NPC227060
0.6353	Remote Similarity	NPC611658
0.6265	Remote Similarity	NPC274716
0.6265	Remote Similarity	NPC167116
0.6265	Remote Similarity	NPC609821
0.6184	Remote Similarity	NPC30779
0.6136	Remote Similarity	NPC480586
0.6136	Remote Similarity	NPC480590
0.6087	Remote Similarity	NPC175890
0.6076	Remote Similarity	NPC41376
0.6053	Remote Similarity	NPC317272
0.6053	Remote Similarity	NPC268503
0.6026	Remote Similarity	NPC256012
0.6026	Remote Similarity	NPC610965
0.5949	Remote Similarity	NPC480592
0.593	Remote Similarity	NPC16357
0.593	Remote Similarity	NPC302245
0.593	Remote Similarity	NPC195538
0.5926	Remote Similarity	NPC240841
0.5862	Remote Similarity	NPC243454
0.5833	Remote Similarity	NPC317439
0.5732	Remote Similarity	NPC610959
0.5714	Remote Similarity	NPC608819
0.5682	Remote Similarity	NPC475479
0.5682	Remote Similarity	NPC323537
0.5647	Remote Similarity	NPC475393
0.5638	Remote Similarity	NPC48490
0.5618	Remote Similarity	NPC485712
0.5532	Remote Similarity	NPC41122
0.5532	Remote Similarity	NPC318805
0.5495	Remote Similarity	NPC10871
0.5495	Remote Similarity	NPC239584
0.5476	Remote Similarity	NPC480591
0.5465	Remote Similarity	NPC600872
0.5429	Remote Similarity	NPC213206
0.5429	Remote Similarity	NPC188163
0.5429	Remote Similarity	NPC328750
0.5405	Remote Similarity	NPC135538
0.5405	Remote Similarity	NPC24233
0.5376	Remote Similarity	NPC206900
0.5376	Remote Similarity	NPC281581
0.5333	Remote Similarity	NPC139783
0.5333	Remote Similarity	NPC65312
0.5333	Remote Similarity	NPC601489
0.5333	Remote Similarity	NPC604804
0.5333	Remote Similarity	NPC611798
0.5319	Remote Similarity	NPC485711
0.5287	Remote Similarity	NPC600054
0.5287	Remote Similarity	NPC601504
0.5286	Remote Similarity	NPC314682
0.5275	Remote Similarity	NPC249996
0.5213	Remote Similarity	NPC254581
0.5205	Remote Similarity	NPC185838
0.5109	Remote Similarity	NPC605743
0.5102	Remote Similarity	NPC201508
0.5098	Remote Similarity	NPC82056
0.5067	Remote Similarity	NPC147390
0.5067	Remote Similarity	NPC428
0.5056	Remote Similarity	NPC601503
0.5053	Remote Similarity	NPC473589
0.5052	Remote Similarity	NPC475597

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC306863 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4611
0.1-0.2	4423
0.2-0.3	101
0.3-0.4	8
0.4-0.5	1
0.5-0.6	2
0.6-0.7	1
0.7-0.8	3
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
0.7746	Intermediate Similarity	NPD8099	Discontinued
0.7333	Intermediate Similarity	NPD8156	Discontinued
0.7013	Intermediate Similarity	NPD8095	Phase 1
0.6087	Remote Similarity	NPD8054	Phase 4
0.5429	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.5155	Remote Similarity	NPD8053	Approved

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