NPASS Compound

Natural Product: NPC475066

Natural Product ID	NPC475066
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	1-O-Deacetylohchinolide B
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL495473
PubChem CID	11421886
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

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 84 89 0 0 0 0 0 0 0 0999 V2000 -0.6803 5.5681 -2.0475 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9414 4.5659 -0.9768 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4156 3.3522 -0.9955 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7128 2.4265 0.0809 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4666 2.7676 1.0335 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2494 1.1526 0.1988 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4886 0.2172 1.1892 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8880 0.0517 1.8732 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3844 1.2616 2.3149 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6605 1.4776 1.7485 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1111 0.0840 1.2627 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7594 -0.2753 0.7250 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5880 -1.5262 0.0191 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1405 -1.8174 -0.1997 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8642 -1.1570 0.7033 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1090 -1.9798 1.9469 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1568 -1.0853 -0.0910 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3002 -0.6236 0.3979 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5738 -0.1004 1.7468 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3903 -0.6761 -0.6419 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7889 -1.2799 -1.8396 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3621 -1.4710 -1.5391 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0150 -2.7867 -1.8366 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9282 -3.5873 -1.5192 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5498 -4.5104 -2.2337 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1891 -3.2939 -0.2303 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5769 -1.3814 -0.1240 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8492 -0.8790 0.0296 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6413 -1.8810 0.5452 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8928 -2.9352 0.6973 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6499 -2.6851 0.3106 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3715 -2.7167 0.5701 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3321 -1.2768 -1.3205 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3265 -0.1795 -1.2362 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9885 0.1236 0.0535 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5112 1.4474 -0.0235 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8600 1.7407 0.0195 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6921 0.7789 0.1344 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3054 3.1483 -0.0677 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3926 -0.8811 -2.3086 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6041 -0.6217 2.4461 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4586 3.0320 -2.1486 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4062 5.6628 -2.2477 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2653 5.2940 -2.9378 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0411 6.5463 -1.6710 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5835 4.8107 -0.1367 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1390 0.5000 2.0050 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8886 -0.7261 2.6237 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3842 1.8341 2.5047 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5519 2.1718 0.9053 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5604 0.5674 -0.0243 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0792 -1.3965 -1.2198 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0224 -1.3722 2.9020 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0285 -2.5839 1.9235 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2847 -2.7201 2.1243 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1706 -0.6343 2.5918 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6988 -0.1550 1.9529 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4382 1.0254 1.7990 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6965 0.3842 -0.9075 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9026 -0.6088 -2.7429 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3005 -2.2378 -2.1501 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7472 -0.7716 -2.1801 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6295 -3.9742 -0.0563 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9786 -3.5866 0.5128 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2002 0.1157 -0.2016 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6896 -1.7661 0.7674 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8769 -3.4369 0.3601 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4261 -2.3280 0.6957 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9615 -3.1732 1.4503 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5418 -3.4357 -0.2906 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7835 -2.1850 -1.7261 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9036 0.7928 -1.6305 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1459 -0.4122 -1.9806 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9037 -0.5318 0.1497 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9791 3.6462 0.8728 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8018 3.6506 -0.9266 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3896 3.2534 -0.1224 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7927 -0.2206 -2.9291 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6474 -1.0276 2.2852 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7490 0.0453 3.3522 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9221 -1.4263 2.8511 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0213 3.3084 -3.1099 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4341 3.5701 -1.9616 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7373 1.9431 -2.1435 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 4 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 0 15 16 1 1 15 17 1 0 17 18 2 0 18 19 1 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 20 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 13 32 1 1 13 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 33 40 1 0 11 41 1 1 3 42 1 0 15 7 1 0 22 17 1 0 31 27 2 0 12 8 1 0 26 14 1 0 35 11 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 7 47 1 1 8 48 1 1 10 49 1 0 10 50 1 0 12 51 1 6 14 52 1 6 16 53 1 0 16 54 1 0 16 55 1 0 19 56 1 0 19 57 1 0 19 58 1 0 20 59 1 6 21 60 1 0 21 61 1 0 22 62 1 6 26 63 1 0 26 64 1 0 28 65 1 0 29 66 1 0 31 67 1 0 32 68 1 0 32 69 1 0 32 70 1 0 33 71 1 6 34 72 1 0 34 73 1 0 35 74 1 1 39 75 1 0 39 76 1 0 39 77 1 0 40 78 1 0 41 79 1 0 41 80 1 0 41 81 1 0 42 82 1 0 42 83 1 0 42 84 1 0 M END

Standard InCHIKey	LHFRBMWFNLUYCY-ABMVXICKSA-N
Standard InCHI	InChI=1S/C33H42O9/c1-8-16(2)30(37)42-29-27-28-31(5,15-39-27)24(40-18(4)34)13-23(35)32(28,6)22-12-25(36)41-21-11-20(19-9-10-38-14-19)17(3)26(21)33(22,29)7/h8-10,14,20-24,27-29,35H,11-13,15H2,1-7H3/b16-8+/t20-,21+,22-,23+,24-,27-,28+,29-,31-,32+,33-/m1/s1
SMILES	C/C=C(/C(=O)O[C@@H]1[C@@H]2OC[C@]3([C@H]2[C@]([C@@H]2[C@]1(C)C1=C(C)[C@@H](C[C@@H]1OC(=O)C2)c1ccoc1)(C)[C@H](C[C@H]3OC(=O)C)O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	582.28	Volume:	588.642 ? Van der Waals volume.
Dense:	0.989	LogP:	2.745 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.804 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.441 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	33.0
TPSA:	121.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.234	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.634	Fsp³:	0.667
MCE-18:	148.909 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.963	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.033 ? 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:	0.024	Promiscuous compounds:	0.421

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.188	MDCK Permeability:	-4.828
Pgp-inhibitor:	0.223	Pgp-substrate:	0.786
PAMPA:	0.926 ? 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):	0.0
20% Bioavailability (F20%):	0.948	30% Bioavailability (F30%):	0.933
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044	MRP1:	1.0
Plasma Protein Binding (PPB):	90.506%	Volume Distribution (VD):	-0.315
Fu:	8.777% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.702	BCRP inhibitor:	0.038
BSEP inhibitor:	0.939

ADMET: Metabolism

CYP1A2-inhibitor:	0.032	CYP1A2-substrate:	0.569
CYP2C19-inhibitor:	0.63	CYP2C19-substrate:	0.027
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.356
CYP3A4-inhibitor:	0.992	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.983 ? 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):

8.992

Half-life (T1/2):

1.236

ADMET: Toxicity

hERG Blockers:	0.054	hERG Blockers (10um):	0.143
Human Hepatotoxicity (H-HT):	0.7	Drug-induced Liver Injury (DILI):	0.984
AMES Toxicity:	0.817	Rat Oral Acute Toxicity:	0.836
Maximum Recommended Daily Dose:	0.989	Skin Sensitization:	0.997
Carcinogencity:	0.895	Eye Corrosion:	0.0
Eye Irritation:	0.118	Respiratory Toxicity:	0.517
Drug-induced Neurotoxicity:	0.554	Ototoxicity:	0.719
Hematotoxicity:	0.623	Drug-induced Nephrotoxicity:	0.98
Genotoxicity:	0.995	RPMI-8226 Immunitoxicity:	0.252
A549 Cytotoxicity:	0.857	Hek293 Cytotoxicity:	0.404
BCF:	0.695 ? 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:	3.515 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.41 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.76 ? 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
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[15387656]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	ripe fruit	n.a.	PMID[16205005]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[33253570]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36362399]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[3701342]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932	Melia azedarach	Species	Meliaceae	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

Activity Type	# Activity
Activity	1
IC50	1

Activity Type	# Activity
Organism	1
Non-molecular	1

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	100.0	nM	PMID[15387656]
NPT140	Organism	Artemia	Artemia	Activity	=	100.0	%	PMID[23398362]

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 NPC475066 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	10207
0.1-0.2	36685
0.2-0.3	2809
0.3-0.4	111
0.4-0.5	19
0.5-0.6	16
0.6-0.7	7
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
0.7882	Intermediate Similarity	NPC118086
0.7654	Intermediate Similarity	NPC182427
0.7561	Intermediate Similarity	NPC29695
0.6739	Remote Similarity	NPC126984
0.6667	Remote Similarity	NPC214495
0.6667	Remote Similarity	NPC470119
0.6629	Remote Similarity	NPC308205
0.6489	Remote Similarity	NPC27541
0.6129	Remote Similarity	NPC475226
0.6022	Remote Similarity	NPC62692
0.5638	Remote Similarity	NPC322546
0.5604	Remote Similarity	NPC604850
0.5579	Remote Similarity	NPC610307
0.5567	Remote Similarity	NPC608851
0.5347	Remote Similarity	NPC61967
0.5326	Remote Similarity	NPC469380
0.53	Remote Similarity	NPC307781
0.53	Remote Similarity	NPC472670
0.53	Remote Similarity	NPC264690
0.53	Remote Similarity	NPC601577
0.5253	Remote Similarity	NPC472671
0.5217	Remote Similarity	NPC291150
0.5213	Remote Similarity	NPC469382
0.5052	Remote Similarity	NPC469379
0.5052	Remote Similarity	NPC75856
0.5051	Remote Similarity	NPC488535

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475066 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3462
0.1-0.2	5654
0.2-0.3	34
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
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
		NPD

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