NPASS Compound

Natural Product: NPC474963

Natural Product ID	NPC474963
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Lantanolic Acid
IUPAC Name	n.a.
Synonyms	Lantanolic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL490344
PubChem CID	15560079
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 2D 80 85 0 0 0 0 0 0 0 0999 V2000 3.0000 -10.3923 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2500 -9.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -9.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 -0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4000 -0.6928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 -9.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -9.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1491 -8.7584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1491 -6.8300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2500 -11.6913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0905 -8.3073 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2137 -9.2666 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6683 -6.0070 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2730 -7.5922 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 -3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1047 -1.1017 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4095 -2.0850 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4991 -2.6503 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7947 -1.3259 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 -4.4101 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0363 -5.3695 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9673 -2.2864 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 -3.5623 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2054 -1.6620 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 0.9642 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8482 -0.6575 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4895 2.7762 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 1.8121 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7981 -1.9284 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7461 0.0588 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1608 -2.3825 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7981 1.9284 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9916 2.3124 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7461 -0.0588 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8547 -2.7954 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2116 -1.6364 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3361 -5.1144 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5865 -5.8142 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1715 -4.9972 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9895 -10.5705 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5865 -9.7743 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6180 -10.0774 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0105 -10.5705 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2981 -9.7226 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3321 -10.0164 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2461 -7.7354 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2981 -5.8659 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2461 -7.8530 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3321 -5.5720 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -5.1962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7044 -3.8718 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5377 -6.5965 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 4 2 1 1 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 20 24 1 0 24 25 1 0 20 26 1 1 8 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 29 33 1 0 7 34 1 6 31 4 1 0 27 4 1 0 12 7 1 0 21 16 1 0 17 11 1 0 25 17 1 0 1 35 1 0 5 36 1 0 5 37 1 0 6 38 1 0 6 39 1 0 9 40 1 0 10 41 1 0 10 42 1 0 11 43 1 6 13 44 1 0 13 45 1 0 13 46 1 0 14 47 1 0 14 48 1 0 15 49 1 0 15 50 1 0 16 51 1 6 18 52 1 0 18 53 1 0 19 54 1 0 19 55 1 0 22 56 1 0 22 57 1 0 22 58 1 0 23 59 1 0 23 60 1 0 23 61 1 0 25 62 1 0 25 63 1 0 26 64 1 0 27 65 1 1 28 66 1 0 28 67 1 0 30 68 1 0 30 69 1 0 31 70 1 0 31 71 1 0 32 72 1 0 32 73 1 0 32 74 1 0 33 75 1 0 33 76 1 0 33 77 1 0 34 78 1 0 34 79 1 0 34 80 1 0 M END

Standard InCHIKey	UFVGYQQCHANGSN-XFGDDKMHSA-N
Standard InCHI	InChI=1S/C30H46O4/c1-24(2)11-13-28(23(31)32)14-12-26(5)19(20(28)17-24)7-8-22-27(26,6)10-9-21-25(3,4)30(33)16-15-29(21,22)18-34-30/h7,20-22,33H,8-18H2,1-6H3,(H,31,32)/t20-,21-,22-,26+,27+,28-,29+,30+/m0/s1
SMILES	OC(=O)[C@]12CC[C@@]3(C(=CC[C@H]4[C@@]3(C)CC[C@@H]3[C@@]54CC[C@](C3(C)C)(OC5)O)[C@@H]2CC(CC1)(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	505.985 ? Van der Waals volume.
Dense:	0.93	LogP:	3.187 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.965 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.445 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	30.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	7.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.425	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.109	Fsp³:	0.9
MCE-18:	164.421 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.591	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.344	Promiscuous compounds:	0.151

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.353	MDCK Permeability:	-5.012
Pgp-inhibitor:	0.116	Pgp-substrate:	0.021
PAMPA:	0.945 ? 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%):	0.849	30% Bioavailability (F30%):	0.074
50% Bioavailability (F50%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.224	MRP1:	0.997
Plasma Protein Binding (PPB):	94.931%	Volume Distribution (VD):	-0.221
Fu:	4.886% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.516	BCRP inhibitor:	0.003
BSEP inhibitor:	0.99

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.577	CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.039	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.013
CYP3A4-inhibitor:	0.321	CYP3A4-substrate:	0.008
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.238
HLM stability:	0.67 ? 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):

4.225

Half-life (T1/2):

0.982

ADMET: Toxicity

hERG Blockers:	0.097	hERG Blockers (10um):	0.139
Human Hepatotoxicity (H-HT):	0.637	Drug-induced Liver Injury (DILI):	0.315
AMES Toxicity:	0.088	Rat Oral Acute Toxicity:	0.551
Maximum Recommended Daily Dose:	0.77	Skin Sensitization:	0.898
Carcinogencity:	0.679	Eye Corrosion:	0.021
Eye Irritation:	0.431	Respiratory Toxicity:	0.659
Drug-induced Neurotoxicity:	0.083	Ototoxicity:	0.529
Hematotoxicity:	0.14	Drug-induced Nephrotoxicity:	0.674
Genotoxicity:	0.838	RPMI-8226 Immunitoxicity:	0.053
A549 Cytotoxicity:	0.026	Hek293 Cytotoxicity:	0.289
BCF:	1.665 ? 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:	3.938 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.429 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.782 ? 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
NPO6442	Lippia turbinata	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170663]
NPO32560	liquidamber styraciflua	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16441087]
NPO6442	Lippia turbinata	Species	Verbenaceae	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
MIC	1
ED50	2

Activity Type	# Activity
Cell line	2
Organism	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
NPT168	Cell line	P388	Mus musculus	ED50	=	23.97	uM	PMID[10924160]
NPT81	Cell line	A549	Homo sapiens	ED50	=	26.52	uM	PMID[10479314]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	128000.0	nM	PMID[15568791]

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 NPC474963 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	20231
0.1-0.2	26603
0.2-0.3	2496
0.3-0.4	274
0.4-0.5	184
0.5-0.6	45
0.6-0.7	17
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
0.6974	Remote Similarity	NPC473576
0.6944	Remote Similarity	NPC474727
0.6883	Remote Similarity	NPC473483
0.6883	Remote Similarity	NPC475570
0.6522	Remote Similarity	NPC480946
0.6522	Remote Similarity	NPC130577
0.6522	Remote Similarity	NPC142415
0.6522	Remote Similarity	NPC102683
0.6296	Remote Similarity	NPC110861
0.6296	Remote Similarity	NPC268954
0.6296	Remote Similarity	NPC44170
0.6203	Remote Similarity	NPC475156
0.6197	Remote Similarity	NPC270768
0.6197	Remote Similarity	NPC59263
0.6197	Remote Similarity	NPC210106
0.6111	Remote Similarity	NPC158141
0.6027	Remote Similarity	NPC298554
0.5972	Remote Similarity	NPC84319
0.5972	Remote Similarity	NPC52021
0.5972	Remote Similarity	NPC599947
0.5942	Remote Similarity	NPC604575
0.5921	Remote Similarity	NPC96580
0.589	Remote Similarity	NPC231063
0.589	Remote Similarity	NPC282395
0.589	Remote Similarity	NPC481360
0.589	Remote Similarity	NPC110308
0.5753	Remote Similarity	NPC282616
0.5753	Remote Similarity	NPC275809
0.5753	Remote Similarity	NPC37038
0.5676	Remote Similarity	NPC106112
0.5676	Remote Similarity	NPC261935
0.56	Remote Similarity	NPC200752
0.56	Remote Similarity	NPC120840
0.5556	Remote Similarity	NPC280654
0.5541	Remote Similarity	NPC182797
0.5541	Remote Similarity	NPC156981
0.5541	Remote Similarity	NPC52169
0.5541	Remote Similarity	NPC488562
0.5412	Remote Similarity	NPC607691
0.5405	Remote Similarity	NPC198664
0.5385	Remote Similarity	NPC296164
0.5357	Remote Similarity	NPC204407
0.5333	Remote Similarity	NPC121798
0.5333	Remote Similarity	NPC64872
0.5333	Remote Similarity	NPC25906
0.5333	Remote Similarity	NPC475061
0.5333	Remote Similarity	NPC234346
0.5294	Remote Similarity	NPC283849
0.5294	Remote Similarity	NPC28198
0.5294	Remote Similarity	NPC476123
0.5294	Remote Similarity	NPC606107
0.5275	Remote Similarity	NPC198621
0.5275	Remote Similarity	NPC216940
0.5263	Remote Similarity	NPC130278
0.52	Remote Similarity	NPC474806
0.52	Remote Similarity	NPC133579
0.5132	Remote Similarity	NPC307282
0.5132	Remote Similarity	NPC32118
0.5114	Remote Similarity	NPC100383
0.5065	Remote Similarity	NPC472149
0.5065	Remote Similarity	NPC609452
0.5063	Remote Similarity	NPC130520

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474963 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5668
0.1-0.2	3451
0.2-0.3	27
0.3-0.4	3
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