NPASS Compound

Natural Product: NPC55539

Natural Product ID	NPC55539
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OOJYZGOXKZKJPE-JCRFDYJRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101642551
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

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 88 0 0 0 0 0 0 0 0999 V2000 -0.4370 1.4228 -1.2481 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1061 0.3413 -0.3722 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4835 -0.9719 -0.9106 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9716 -0.9162 -0.9698 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6479 -0.4043 0.2436 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9163 0.6436 1.0086 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4275 0.4681 1.0402 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1623 -0.8315 1.8120 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2894 -1.1704 1.7512 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0943 -0.1068 1.0587 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5761 0.2295 -0.3153 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3401 1.4508 -0.7519 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7750 1.0240 -0.9656 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4194 0.3333 0.1694 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1200 1.3729 1.0301 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4229 -0.6650 -0.4186 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2904 -1.9004 0.4498 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7630 -1.9248 0.6261 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5220 -0.5029 1.0292 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9964 -0.3913 2.3597 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8008 -0.1466 -0.4424 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8577 -0.6295 0.1998 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0238 0.1789 -0.0980 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2079 0.0432 0.3175 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6262 1.1850 -0.9583 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2389 1.0325 -1.2301 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9037 2.0113 -1.9230 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8731 0.1603 -0.1667 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9625 -0.5082 0.3910 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6996 0.5461 1.2273 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4211 1.4271 0.2337 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5400 0.6191 -0.3642 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1034 -0.8138 -0.4348 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8301 -1.4807 -1.5823 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5138 -2.8466 -1.6583 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7420 -0.9643 -0.6569 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6553 0.7345 0.4714 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8332 2.6267 0.7750 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5206 -0.0141 2.1698 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5634 1.3597 -1.1658 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2393 1.1800 -2.3196 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1782 2.4386 -0.9583 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1158 -1.0160 -1.9787 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0681 -1.8471 -0.4148 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2955 -0.3920 -1.9080 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3242 -1.9789 -1.1259 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9198 -1.2617 0.9270 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2607 0.5574 2.0834 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2230 1.6953 0.7313 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0092 1.2946 1.5995 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5141 -0.6040 2.8611 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8343 -1.6468 1.4650 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6618 -1.1924 2.8182 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4988 -2.1969 1.3683 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0022 0.8210 1.6717 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9046 -0.6012 -1.0071 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2901 2.1841 0.0978 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3922 1.8893 -1.2778 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7481 0.3249 -1.8508 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9861 2.4074 0.6317 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1587 1.1251 1.2613 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5953 1.4044 2.0265 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1500 -0.9646 -1.4500 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8020 -1.8069 1.4079 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6329 -2.7947 -0.1255 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3052 -2.1985 -0.3361 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5305 -2.6472 1.4301 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9635 -1.2610 2.8251 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8285 -1.4917 0.8389 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7525 1.9453 -0.8994 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0871 0.8537 -2.3269 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1396 2.9830 -1.9417 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6284 -1.3500 1.0449 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9007 1.1395 1.7261 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6799 1.6179 -0.5970 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7748 1.0214 -1.3732 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3518 -1.3951 0.4769 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5714 -1.0479 -2.5651 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9440 -1.4247 -1.4384 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8306 -3.3150 -0.8260 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8904 1.7105 0.4756 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4822 3.3815 0.2228 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4817 0.4376 3.0634 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 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 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 1 16 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 12 27 1 0 5 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 32 37 1 0 31 38 1 0 30 39 1 0 7 2 1 0 19 10 1 0 26 21 1 0 36 29 1 0 11 2 1 0 19 14 1 0 1 40 1 0 1 41 1 0 1 42 1 0 3 43 1 0 3 44 1 0 4 45 1 0 4 46 1 0 5 47 1 1 6 48 1 0 6 49 1 0 7 50 1 1 8 51 1 0 8 52 1 0 9 53 1 0 9 54 1 0 10 55 1 1 11 56 1 6 12 57 1 1 13 58 1 0 13 59 1 0 15 60 1 0 15 61 1 0 15 62 1 0 16 63 1 6 17 64 1 0 17 65 1 0 18 66 1 0 18 67 1 0 20 68 1 0 22 69 1 0 26 70 1 0 26 71 1 0 27 72 1 0 29 73 1 1 30 74 1 1 31 75 1 6 32 76 1 6 33 77 1 1 34 78 1 0 34 79 1 0 35 80 1 0 37 81 1 0 38 82 1 0 39 83 1 0 M END

Standard InCHIKey	OOJYZGOXKZKJPE-JCRFDYJRSA-N
Standard InCHI	InChI=1S/C29H44O10/c1-27-7-5-16(38-26-25(35)24(34)23(33)20(12-30)39-26)10-15(27)3-4-18-22(27)19(31)11-28(2)17(6-8-29(18,28)36)14-9-21(32)37-13-14/h9,15-20,22-26,30-31,33-36H,3-8,10-13H2,1-2H3/t15-,16+,17-,18-,19-,20-,22-,23-,24-,25-,26-,27+,28-,29+/m1/s1
SMILES	C[C@]12CC[C@@H](C[C@H]1CC[C@@H]1[C@@H]2[C@@H](C[C@]2(C)[C@H](CC[C@]12O)C1=CC(=O)OC1)O)O[C@H]1[C@@H]([C@@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	552.29	Volume:	541.431 ? Van der Waals volume.
Dense:	1.02	LogP:	0.191 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.077 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.428 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	32.0
TPSA:	166.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.212	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.208	Fsp³:	0.897
MCE-18:	113.455 ? 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:	0.702	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.118	Promiscuous compounds:	0.317

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.514	MDCK Permeability:	-5.299
Pgp-inhibitor:	0.0	Pgp-substrate:	0.961
PAMPA:	0.998 ? 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):	0.063
20% Bioavailability (F20%):	0.711	30% Bioavailability (F30%):	0.525
50% Bioavailability (F50%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011	MRP1:	0.842
Plasma Protein Binding (PPB):	62.089%	Volume Distribution (VD):	-0.472
Fu:	35.638% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.96
OATP1B3 inhibitor:	0.917	BCRP inhibitor:	0.011
BSEP inhibitor:	0.018

ADMET: Metabolism

CYP1A2-inhibitor:	0.008	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.113	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.008	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.602	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.596
HLM stability:	0.01 ? 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):

1.775

Half-life (T1/2):

2.767

ADMET: Toxicity

hERG Blockers:	0.147	hERG Blockers (10um):	0.408
Human Hepatotoxicity (H-HT):	0.774	Drug-induced Liver Injury (DILI):	0.29
AMES Toxicity:	0.881	Rat Oral Acute Toxicity:	0.935
Maximum Recommended Daily Dose:	0.999	Skin Sensitization:	1.0
Carcinogencity:	0.702	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.946
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.961
Hematotoxicity:	0.761	Drug-induced Nephrotoxicity:	0.933
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.801
A549 Cytotoxicity:	0.899	Hek293 Cytotoxicity:	0.977
BCF:	0.587 ? 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:	3.18 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.535 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.856 ? 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
NPO28744	Murraya crenulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28744	Murraya crenulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28744	Murraya crenulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28744	Murraya crenulata	Species	Rutaceae	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 NPC55539 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	13926
0.1-0.2	29457
0.2-0.3	5127
0.3-0.4	1100
0.4-0.5	97
0.5-0.6	90
0.6-0.7	46
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
0.8289	Intermediate Similarity	NPC5311
0.7595	Intermediate Similarity	NPC77299
0.7595	Intermediate Similarity	NPC480906
0.759	Intermediate Similarity	NPC30483
0.759	Intermediate Similarity	NPC470897
0.75	Intermediate Similarity	NPC236973
0.75	Intermediate Similarity	NPC480914
0.7342	Intermediate Similarity	NPC99620
0.7294	Intermediate Similarity	NPC292467
0.7241	Intermediate Similarity	NPC486143
0.7241	Intermediate Similarity	NPC486142
0.7241	Intermediate Similarity	NPC486149
0.7143	Intermediate Similarity	NPC480907
0.7073	Intermediate Similarity	NPC76572
0.7073	Intermediate Similarity	NPC193382
0.7011	Intermediate Similarity	NPC240070
0.6932	Remote Similarity	NPC264336
0.6897	Remote Similarity	NPC32177
0.6897	Remote Similarity	NPC469756
0.6897	Remote Similarity	NPC275901
0.6889	Remote Similarity	NPC486146
0.6818	Remote Similarity	NPC188234
0.6818	Remote Similarity	NPC480910
0.6818	Remote Similarity	NPC480909
0.6774	Remote Similarity	NPC486144
0.6774	Remote Similarity	NPC486145
0.6774	Remote Similarity	NPC486147
0.6774	Remote Similarity	NPC486148
0.6747	Remote Similarity	NPC469750
0.6667	Remote Similarity	NPC59288
0.6667	Remote Similarity	NPC486135
0.6667	Remote Similarity	NPC486137
0.6632	Remote Similarity	NPC74259
0.6627	Remote Similarity	NPC84987
0.6596	Remote Similarity	NPC475590
0.6593	Remote Similarity	NPC232785
0.6593	Remote Similarity	NPC486139
0.6562	Remote Similarity	NPC474908
0.6484	Remote Similarity	NPC125077
0.6484	Remote Similarity	NPC208193
0.6458	Remote Similarity	NPC120390
0.6458	Remote Similarity	NPC475419
0.6392	Remote Similarity	NPC486134
0.6392	Remote Similarity	NPC486141
0.6344	Remote Similarity	NPC329986
0.6344	Remote Similarity	NPC140092
0.6333	Remote Similarity	NPC40749
0.6322	Remote Similarity	NPC471353
0.6277	Remote Similarity	NPC486138
0.6277	Remote Similarity	NPC276838
0.625	Remote Similarity	NPC486136
0.6235	Remote Similarity	NPC196429
0.6207	Remote Similarity	NPC83287
0.62	Remote Similarity	NPC474423
0.6196	Remote Similarity	NPC231518
0.6196	Remote Similarity	NPC488944
0.6118	Remote Similarity	NPC471633
0.6104	Remote Similarity	NPC160583
0.6087	Remote Similarity	NPC486130
0.6061	Remote Similarity	NPC117445
0.6061	Remote Similarity	NPC308262
0.6022	Remote Similarity	NPC486127
0.5977	Remote Similarity	NPC157376
0.5977	Remote Similarity	NPC142066
0.5977	Remote Similarity	NPC603972
0.5955	Remote Similarity	NPC179412
0.5955	Remote Similarity	NPC471356
0.593	Remote Similarity	NPC99728
0.593	Remote Similarity	NPC87250
0.593	Remote Similarity	NPC244402
0.593	Remote Similarity	NPC50305
0.5914	Remote Similarity	NPC32793
0.5914	Remote Similarity	NPC116075
0.5909	Remote Similarity	NPC199428
0.5909	Remote Similarity	NPC109448
0.5909	Remote Similarity	NPC310341
0.5851	Remote Similarity	NPC475629
0.5842	Remote Similarity	NPC486150
0.5824	Remote Similarity	NPC72260
0.5816	Remote Similarity	NPC479360
0.5816	Remote Similarity	NPC479359
0.5816	Remote Similarity	NPC488943
0.5816	Remote Similarity	NPC488942
0.5795	Remote Similarity	NPC17896
0.5795	Remote Similarity	NPC469755
0.5795	Remote Similarity	NPC284406
0.5795	Remote Similarity	NPC197707
0.5795	Remote Similarity	NPC251866
0.5795	Remote Similarity	NPC480915
0.5745	Remote Similarity	NPC475556
0.5745	Remote Similarity	NPC311706
0.573	Remote Similarity	NPC84949
0.573	Remote Similarity	NPC480562
0.573	Remote Similarity	NPC74945
0.573	Remote Similarity	NPC31354
0.573	Remote Similarity	NPC69576
0.5729	Remote Similarity	NPC469749
0.5714	Remote Similarity	NPC475219
0.5714	Remote Similarity	NPC486132
0.5714	Remote Similarity	NPC486131
0.5684	Remote Similarity	NPC488941
0.5684	Remote Similarity	NPC488940
0.5657	Remote Similarity	NPC486128
0.5657	Remote Similarity	NPC488938
0.5657	Remote Similarity	NPC488937
0.5604	Remote Similarity	NPC305574
0.5579	Remote Similarity	NPC479353
0.5579	Remote Similarity	NPC479354
0.5556	Remote Similarity	NPC476221
0.5556	Remote Similarity	NPC477709
0.551	Remote Similarity	NPC146857
0.551	Remote Similarity	NPC247190
0.5506	Remote Similarity	NPC309034
0.5481	Remote Similarity	NPC488945
0.5481	Remote Similarity	NPC488946
0.5474	Remote Similarity	NPC27363
0.5472	Remote Similarity	NPC286809
0.5455	Remote Similarity	NPC158344
0.5437	Remote Similarity	NPC486140
0.5435	Remote Similarity	NPC483822
0.5435	Remote Similarity	NPC484202
0.5435	Remote Similarity	NPC93883
0.5385	Remote Similarity	NPC243196
0.5385	Remote Similarity	NPC486133
0.5361	Remote Similarity	NPC610296
0.5354	Remote Similarity	NPC488939
0.5333	Remote Similarity	NPC219085
0.5326	Remote Similarity	NPC146456
0.5326	Remote Similarity	NPC77319
0.5326	Remote Similarity	NPC250556
0.5326	Remote Similarity	NPC471351
0.5326	Remote Similarity	NPC471355
0.5283	Remote Similarity	NPC488947
0.5263	Remote Similarity	NPC173555
0.5248	Remote Similarity	NPC479357
0.5238	Remote Similarity	NPC329784
0.5213	Remote Similarity	NPC471354
0.5213	Remote Similarity	NPC27507
0.5152	Remote Similarity	NPC55532
0.5143	Remote Similarity	NPC329675
0.5143	Remote Similarity	NPC194716
0.5138	Remote Similarity	NPC486152
0.5106	Remote Similarity	NPC9499
0.5106	Remote Similarity	NPC471360
0.5106	Remote Similarity	NPC469751
0.5106	Remote Similarity	NPC471361
0.5106	Remote Similarity	NPC86159
0.5106	Remote Similarity	NPC469752
0.5106	Remote Similarity	NPC469754
0.5106	Remote Similarity	NPC70542
0.5055	Remote Similarity	NPC473852
0.5054	Remote Similarity	NPC480908

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC55539 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5713
0.1-0.2	3293
0.2-0.3	123
0.3-0.4	6
0.4-0.5	5
0.5-0.6	7
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
0.6207	Remote Similarity	NPD7327	Approved
0.6207	Remote Similarity	NPD7328	Phase 4
0.6196	Remote Similarity	NPD8033	Approved
0.5824	Remote Similarity	NPD8294	Phase 4
0.5795	Remote Similarity	NPD7319	Approved
0.5326	Remote Similarity	NPD7507	Pre-clinical
0.5306	Remote Similarity	NPD8377	Phase 4
0.5263	Remote Similarity	NPD8296	Phase 4
0.5161	Remote Similarity	NPD8335	Phase 4
0.5106	Remote Similarity	NPD8380	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