NPASS Compound

Natural Product: NPC483720

Natural Product ID	NPC483720
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MPHDAXXJNDNMGF-MRRHYTQVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44566890
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 79 84 0 0 0 0 0 0 0 0999 V2000 -4.3657 -2.8753 1.5864 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5249 -2.1388 0.5168 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4298 -0.6934 0.3652 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4888 -0.4749 -0.7442 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0244 0.7400 -1.5163 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7964 1.2093 -0.7657 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2556 2.0350 0.3846 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8397 1.9728 -1.6328 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4844 1.9984 -1.0123 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9959 0.6647 -0.5567 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8472 -0.2347 -1.7328 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9834 0.0206 0.4279 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4582 -1.2237 1.0195 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0116 -1.3612 1.2478 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8716 -0.5250 0.3829 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3176 -0.5516 0.7655 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6331 -0.1603 2.1544 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7704 -2.0042 0.5756 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2543 -2.1413 0.5613 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9314 -1.2987 -0.4644 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4971 0.1274 -0.3360 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2621 0.7721 0.7779 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9609 0.8269 -1.6267 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0325 0.2855 -0.2792 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6197 1.7239 -0.1799 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1543 1.7945 -0.5429 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2908 0.8500 0.2309 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0026 1.4326 1.5803 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3097 -1.3916 -0.2993 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2380 -0.1560 -0.3312 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3126 -1.5897 -1.6062 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8593 -2.6476 -0.8077 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7578 -3.8592 -1.1852 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1276 -2.3794 2.5164 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4543 -3.9504 1.6138 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7246 -0.1210 1.2670 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4889 -0.3880 -0.3322 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7306 0.5096 -2.5536 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8074 1.5256 -1.5698 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9230 3.1005 0.2224 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3786 2.1159 0.4491 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9072 1.7428 1.3694 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8522 1.6569 -2.6965 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2167 3.0333 -1.6450 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7697 2.3374 -1.8187 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4610 2.7911 -0.2549 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0122 -1.3090 -1.5005 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1001 -0.0732 -2.3082 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6535 0.0225 -2.4824 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1282 0.7625 1.2396 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9849 -1.3460 2.0143 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8550 -2.0833 0.4028 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2697 -2.4362 1.0230 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2142 -1.2656 2.3319 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8332 -0.9936 -0.6475 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8064 -0.1291 2.8681 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3895 -0.8633 2.6155 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1363 0.8471 2.2471 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3167 -2.3701 -0.3445 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3762 -2.5978 1.4324 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7078 -1.9964 1.5542 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4659 -3.2135 0.2925 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6910 -1.6400 -1.4912 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3583 0.1423 1.6849 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3238 0.8868 0.4037 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9401 1.8136 0.9988 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8937 0.3692 -2.0112 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2366 1.8891 -1.3745 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1500 0.8865 -2.3585 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6235 -0.0826 -1.2690 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1616 2.2769 -0.9928 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8421 2.2117 0.7654 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1106 1.5702 -1.6491 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7609 2.8249 -0.3778 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9472 1.9144 1.9550 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7473 2.2492 1.5723 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3783 0.6860 2.3123 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7918 -1.3019 -1.1775 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0805 -0.7519 -1.2546 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 1 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 6 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 20 29 1 0 12 30 1 0 4 31 1 0 31 32 1 0 32 33 2 0 32 2 1 0 30 3 1 0 30 6 1 0 27 10 1 0 27 15 1 0 24 16 1 0 1 34 1 0 1 35 1 0 3 36 1 1 4 37 1 1 5 38 1 0 5 39 1 0 7 40 1 0 7 41 1 0 7 42 1 0 8 43 1 0 8 44 1 0 9 45 1 0 9 46 1 0 11 47 1 0 11 48 1 0 11 49 1 0 12 50 1 1 13 51 1 0 13 52 1 0 14 53 1 0 14 54 1 0 15 55 1 6 17 56 1 0 17 57 1 0 17 58 1 0 18 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 20 63 1 6 22 64 1 0 22 65 1 0 22 66 1 0 23 67 1 0 23 68 1 0 23 69 1 0 24 70 1 6 25 71 1 0 25 72 1 0 26 73 1 0 26 74 1 0 28 75 1 0 28 76 1 0 28 77 1 0 29 78 1 0 30 79 1 6 M END

Standard InCHIKey	MPHDAXXJNDNMGF-MRRHYTQVSA-N
Standard InCHI	InChI=1S/C30H46O3/c1-17-23-19(33-25(17)32)16-27(4)14-15-29(6)18(24(23)27)8-9-21-28(5)12-11-22(31)26(2,3)20(28)10-13-30(21,29)7/h18-24,31H,1,8-16H2,2-7H3/t18-,19-,20+,21-,22+,23-,24+,27+,28+,29-,30-/m1/s1
SMILES	C=C1[C@@H]2[C@@H](C[C@]3(C)CC[C@]4(C)[C@H](CC[C@@H]5[C@@]6(C)CC[C@@H](C(C)(C)[C@@H]6CC[C@@]45C)O)[C@@H]23)OC1=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	454.34	Volume:	497.195 ? Van der Waals volume.
Dense:	0.914	LogP:	5.015 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.403 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.135 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	31.0
TPSA:	46.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.334	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.983	Fsp³:	0.9
MCE-18:	114.947 ? 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:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.93	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.299	Promiscuous compounds:	0.263

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.503	MDCK Permeability:	-5.107
Pgp-inhibitor:	0.148	Pgp-substrate:	0.019
PAMPA:	0.752 ? 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):	0.013
20% Bioavailability (F20%):	0.935	30% Bioavailability (F30%):	0.876
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.203	MRP1:	0.79
Plasma Protein Binding (PPB):	98.072%	Volume Distribution (VD):	0.004
Fu:	2.26% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.063
BSEP inhibitor:	0.961

ADMET: Metabolism

CYP1A2-inhibitor:	0.021	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.985	CYP2C19-substrate:	0.16
CYP2C9-inhibitor:	0.029	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.028
CYP3A4-inhibitor:	0.559	CYP3A4-substrate:	0.982
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.965
HLM stability:	0.93 ? 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):

10.964

Half-life (T1/2):

0.706

ADMET: Toxicity

hERG Blockers:	0.047	hERG Blockers (10um):	0.203
Human Hepatotoxicity (H-HT):	0.786	Drug-induced Liver Injury (DILI):	0.844
AMES Toxicity:	0.876	Rat Oral Acute Toxicity:	0.561
Maximum Recommended Daily Dose:	0.841	Skin Sensitization:	0.999
Carcinogencity:	0.956	Eye Corrosion:	0.115
Eye Irritation:	0.685	Respiratory Toxicity:	0.854
Drug-induced Neurotoxicity:	0.387	Ototoxicity:	0.468
Hematotoxicity:	0.892	Drug-induced Nephrotoxicity:	0.958
Genotoxicity:	0.896	RPMI-8226 Immunitoxicity:	0.16
A549 Cytotoxicity:	0.831	Hek293 Cytotoxicity:	0.658
BCF:	2.35 ? 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:	4.458 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.495 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.189 ? 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
NPO23500	Lophopetalum wallichii	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8759161]
NPO23500	Lophopetalum wallichii	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO23500	Lophopetalum wallichii	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO23500	Lophopetalum wallichii	Species	n.a.	n.a.	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
IC50	1
EC50	11

Activity Type	# Activity
Cell line	8
Others	1
Non-molecular	3

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
NPT2049	Cell line	HT	Homo sapiens	EC50	=	9.6	ug.mL-1	PMID[8759161]
NPT1034	Cell line	Lu1	Homo sapiens	EC50	=	8.9	ug.mL-1	PMID[8759161]
NPT147	Cell line	SK-MEL-2	Homo sapiens	EC50	>	20.0	ug.mL-1	PMID[8759161]
NPT91	Cell line	KB	Homo sapiens	EC50	>	20.0	ug.mL-1	PMID[8759161]
NPT762	Cell line	A-431	Homo sapiens	EC50	=	6.8	ug.mL-1	PMID[8759161]
NPT858	Cell line	LNCaP	Homo sapiens	EC50	=	14.5	ug.mL-1	PMID[8759161]
NPT133	Cell line	ZR-75-1	Homo sapiens	EC50	=	3.0	ug.mL-1	PMID[8759161]
NPT1851	Cell line	Col2	Homo sapiens	EC50	=	12.1	ug.mL-1	PMID[8759161]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	10.2	ug.mL-1	PMID[8759161]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	>	20.0	ug.mL-1	PMID[8759161]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	9.1	ug.mL-1	PMID[8759161]
NPT2	Others	Unspecified	n.a.	IC50	>	100.0	ug.mL-1	PMID[8759161]

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 NPC483720 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	19759
0.1-0.2	23333
0.2-0.3	6026
0.3-0.4	612
0.4-0.5	86
0.5-0.6	36
0.6-0.7	5
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
0.7097	Intermediate Similarity	NPC475700
0.6032	Remote Similarity	NPC269396
0.6029	Remote Similarity	NPC221421
0.6	Remote Similarity	NPC192638
0.6	Remote Similarity	NPC25511
0.6	Remote Similarity	NPC600137
0.5902	Remote Similarity	NPC97534
0.5902	Remote Similarity	NPC195155
0.5882	Remote Similarity	NPC280877
0.5846	Remote Similarity	NPC12774
0.5821	Remote Similarity	NPC607755
0.5806	Remote Similarity	NPC144075
0.5806	Remote Similarity	NPC301226
0.5781	Remote Similarity	NPC74595
0.5781	Remote Similarity	NPC264665
0.5714	Remote Similarity	NPC248830
0.5714	Remote Similarity	NPC231256
0.5714	Remote Similarity	NPC212241
0.5714	Remote Similarity	NPC178383
0.5667	Remote Similarity	NPC142712
0.5625	Remote Similarity	NPC5767
0.5625	Remote Similarity	NPC475742
0.5606	Remote Similarity	NPC603388
0.5574	Remote Similarity	NPC480925
0.5574	Remote Similarity	NPC48079
0.5538	Remote Similarity	NPC119355
0.5469	Remote Similarity	NPC58631
0.5441	Remote Similarity	NPC201406
0.5441	Remote Similarity	NPC289486
0.5424	Remote Similarity	NPC232112
0.5385	Remote Similarity	NPC201725
0.5362	Remote Similarity	NPC481321
0.5362	Remote Similarity	NPC112009
0.5303	Remote Similarity	NPC246956
0.5224	Remote Similarity	NPC298168
0.5224	Remote Similarity	NPC143133
0.5152	Remote Similarity	NPC602784
0.5143	Remote Similarity	NPC131665
0.5143	Remote Similarity	NPC255387
0.5077	Remote Similarity	NPC245869
0.5077	Remote Similarity	NPC104387
0.5072	Remote Similarity	NPC477577

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC483720 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6868
0.1-0.2	2187
0.2-0.3	90
0.3-0.4	4
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