NPASS Compound

Natural Product: NPC485882

Natural Product ID	NPC485882
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JPZKPTYPWSCQTN-LTFTTYLTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 93 98 0 0 0 0 0 0 0 0999 V2000 -6.0499 1.8633 3.1844 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1070 1.0722 1.8534 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2411 -0.3486 2.2036 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1634 -1.2403 1.6409 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9900 -0.9156 0.1778 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3243 -1.9792 -0.6026 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0406 -1.6501 -1.2634 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1760 -0.8331 -0.3841 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8401 -1.6234 0.8368 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9176 0.4437 -0.0626 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2665 1.5898 0.1006 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8042 1.7978 0.0031 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1581 0.4821 -0.1406 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3520 0.5494 -0.3368 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7236 1.1515 -1.6550 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9114 1.4477 0.7424 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4017 1.4769 0.7540 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0738 0.1360 0.7083 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2855 -0.9992 0.1902 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4771 -2.1802 1.1632 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9657 -1.4909 -1.0992 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8535 -0.8227 -0.1068 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3634 -1.6583 -1.2861 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1008 -1.6364 -1.4885 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8553 -0.4409 -1.0853 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3290 0.3539 -2.3123 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3437 0.2196 0.0404 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5584 0.0851 0.6472 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5446 -0.1321 1.9076 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8264 0.1778 -0.0698 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0375 0.0448 0.5263 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1881 0.1484 -0.2352 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1647 0.3841 -1.5933 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9262 0.5191 -2.1973 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7674 0.4142 -1.4273 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6359 0.5138 -2.5460 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.3834 0.4475 0.0734 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9221 1.4659 1.0150 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3594 2.7341 0.2804 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4035 -0.8449 -0.3658 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7832 0.1865 -0.9307 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2428 -1.9291 -0.2229 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9683 2.9349 3.0043 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1157 1.4930 3.6903 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9023 1.5505 3.8068 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0771 1.4747 1.4209 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2114 -0.7359 1.7826 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3348 -0.4982 3.2968 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4512 -2.3085 1.7103 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2791 -1.0920 2.2619 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2642 -2.8838 0.0780 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9741 -2.3986 -1.4387 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2532 -1.2140 -2.2561 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5303 -2.6232 -1.4901 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5904 -2.4201 1.0953 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8744 -0.9076 1.6969 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8902 -2.1319 0.8712 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9360 2.4476 0.3240 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5297 2.5478 -0.7627 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4891 2.2446 0.9710 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2450 0.0082 0.8852 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8162 1.3439 -1.6819 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2744 2.1879 -1.6695 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4955 0.5518 -2.5317 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5051 1.2185 1.7428 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5866 2.4933 0.4570 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8285 2.0899 -0.0862 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6941 2.0770 1.6695 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3827 -0.0572 1.7834 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5401 -2.7998 1.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5540 -1.8056 2.2088 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3516 -2.7753 0.9170 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7029 -2.5336 -1.3111 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8640 -0.7947 -1.9254 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0649 -1.5057 -0.8340 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2902 -1.2549 0.7509 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9431 -1.4125 -2.2220 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6754 -2.7059 -1.0495 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5684 -2.5627 -1.0666 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2601 -1.7829 -2.6038 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1383 -0.2953 -3.2129 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3874 0.6247 -2.2724 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7785 1.2750 -2.4748 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0599 -0.1405 1.5950 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1505 0.0451 0.2250 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8956 0.7035 -3.2569 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8240 0.5266 -1.9428 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7485 0.7846 -0.9571 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1669 1.8372 1.7465 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0323 2.6573 -0.7970 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4679 2.7759 0.2314 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9695 3.6512 0.7408 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0073 -2.0724 -0.9010 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 1 0 6 7 1 0 7 8 1 0 8 9 1 1 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 18 27 1 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 33 36 1 0 10 37 1 0 37 38 1 0 38 39 1 0 5 40 1 6 40 41 2 0 40 42 1 0 38 2 1 0 37 5 1 0 25 8 1 0 35 30 1 0 25 13 1 0 22 14 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 6 3 47 1 0 3 48 1 0 4 49 1 0 4 50 1 0 6 51 1 0 6 52 1 0 7 53 1 0 7 54 1 0 9 55 1 0 9 56 1 0 9 57 1 0 11 58 1 0 12 59 1 0 12 60 1 0 13 61 1 1 15 62 1 0 15 63 1 0 15 64 1 0 16 65 1 0 16 66 1 0 17 67 1 0 17 68 1 0 18 69 1 1 20 70 1 0 20 71 1 0 20 72 1 0 21 73 1 0 21 74 1 0 21 75 1 0 22 76 1 1 23 77 1 0 23 78 1 0 24 79 1 0 24 80 1 0 26 81 1 0 26 82 1 0 26 83 1 0 31 84 1 0 32 85 1 0 34 86 1 0 35 87 1 0 37 88 1 6 38 89 1 1 39 90 1 0 39 91 1 0 39 92 1 0 42 93 1 0 M END

Standard InCHIKey	JPZKPTYPWSCQTN-LTFTTYLTSA-N
Standard InCHI	InChI=1S/C37H51ClO4/c1-22-14-19-37(32(40)41)21-20-35(6)26(30(37)23(22)2)12-13-28-34(5)17-16-29(33(3,4)27(34)15-18-36(28,35)7)42-31(39)24-8-10-25(38)11-9-24/h8-12,22-23,27-30H,13-21H2,1-7H3,(H,40,41)/t22-,23+,27+,28-,29+,30+,34+,35-,36-,37+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)OC(=O)c3ccc(cc3)Cl)[C@@H]2[C@H]1C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.35	Volume:	631.722 ? Van der Waals volume.
Dense:	0.941	LogP:	7.278 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.059 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.221 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	34.0
TPSA:	63.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.279	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.718	Fsp³:	0.73
MCE-18:	159.5 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.966	Fluc inhibitor:	0.18 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.046 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.22	Promiscuous compounds:	0.127

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.451	MDCK Permeability:	-5.026
Pgp-inhibitor:	0.983	Pgp-substrate:	0.001
PAMPA:	0.936 ? 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%):	0.052	30% Bioavailability (F30%):	0.041
50% Bioavailability (F50%):	0.646

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.483	MRP1:	0.993
Plasma Protein Binding (PPB):	99.113%	Volume Distribution (VD):	-0.211
Fu:	0.524% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.877	BCRP inhibitor:	0.013
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.135	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.995
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.813
HLM stability:	0.001 ? 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):

1.755

Half-life (T1/2):

0.898

ADMET: Toxicity

hERG Blockers:	0.085	hERG Blockers (10um):	0.204
Human Hepatotoxicity (H-HT):	0.38	Drug-induced Liver Injury (DILI):	0.949
AMES Toxicity:	0.108	Rat Oral Acute Toxicity:	0.281
Maximum Recommended Daily Dose:	0.409	Skin Sensitization:	0.953
Carcinogencity:	0.929	Eye Corrosion:	0.008
Eye Irritation:	0.401	Respiratory Toxicity:	0.694
Drug-induced Neurotoxicity:	0.207	Ototoxicity:	0.417
Hematotoxicity:	0.263	Drug-induced Nephrotoxicity:	0.961
Genotoxicity:	0.793	RPMI-8226 Immunitoxicity:	0.021
A549 Cytotoxicity:	0.431	Hek293 Cytotoxicity:	0.477
BCF:	1.627 ? 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:	4.669 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.744 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.379 ? 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
NPO40939	Syzygium corticosum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30057155]

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
IC50	4

Activity Type	# Activity
Cell line	3
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT721	Individual protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	>	10000.0	nM	PMID[30057155]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[30057155]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[30057155]

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 NPC485882 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	14477
0.1-0.2	31871
0.2-0.3	2874
0.3-0.4	459
0.4-0.5	139
0.5-0.6	31
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8533	High Similarity	NPC485585
0.7333	Intermediate Similarity	NPC485589
0.6962	Remote Similarity	NPC485586
0.6962	Remote Similarity	NPC485588
0.686	Remote Similarity	NPC485587
0.6782	Remote Similarity	NPC173569
0.6071	Remote Similarity	NPC230151
0.5823	Remote Similarity	NPC274050
0.5823	Remote Similarity	NPC162632
0.5732	Remote Similarity	NPC173089
0.5679	Remote Similarity	NPC51700
0.5679	Remote Similarity	NPC88716
0.5679	Remote Similarity	NPC68160
0.5663	Remote Similarity	NPC113989
0.5612	Remote Similarity	NPC304110
0.5612	Remote Similarity	NPC27518
0.5612	Remote Similarity	NPC611516
0.5543	Remote Similarity	NPC177246
0.5542	Remote Similarity	NPC120840
0.5435	Remote Similarity	NPC57362
0.5422	Remote Similarity	NPC61543
0.5422	Remote Similarity	NPC293048
0.5422	Remote Similarity	NPC225585
0.54	Remote Similarity	NPC178093
0.5357	Remote Similarity	NPC477288
0.5354	Remote Similarity	NPC172311
0.5294	Remote Similarity	NPC479745
0.5238	Remote Similarity	NPC118033
0.5238	Remote Similarity	NPC71074
0.5238	Remote Similarity	NPC605937
0.52	Remote Similarity	NPC479744
0.5181	Remote Similarity	NPC477289
0.5176	Remote Similarity	NPC87095
0.5176	Remote Similarity	NPC32407
0.5176	Remote Similarity	NPC263548
0.5176	Remote Similarity	NPC606320
0.5057	Remote Similarity	NPC477290
0.5051	Remote Similarity	NPC473481

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC485882 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3085
0.1-0.2	5914
0.2-0.3	142
0.3-0.4	8
0.4-0.5	1
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