NPASS Compound

Natural Product: NPC117122

Natural Product ID	NPC117122
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Lancifoicacid A
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL519944
PubChem CID	11663148
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 83 86 0 0 0 0 0 0 0 0999 V2000 3.3963 -0.0130 -1.6496 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2042 0.0474 -0.1541 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5030 -0.2845 0.5157 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5187 0.7865 0.0658 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8241 0.5646 0.6613 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9207 0.3256 0.0194 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2207 0.1148 0.8030 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0580 0.2233 -1.3992 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1762 -0.0106 -1.9559 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0063 0.3663 -2.2714 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0459 -0.7535 0.3083 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9002 -0.7262 1.8435 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4206 -0.6781 2.1518 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1612 -1.0204 0.7977 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1991 -2.4691 0.6173 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6101 -0.7807 0.6291 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3218 -2.0444 0.1373 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5478 -1.8491 -0.6342 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3525 -0.5905 -0.2798 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2378 -0.7463 0.8588 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7747 -1.1107 2.2118 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1103 0.5000 1.0575 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1817 -1.7588 0.5048 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4649 0.5469 -0.5046 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7268 1.3134 -1.8228 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1355 1.8519 -1.7945 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4168 2.6228 -3.0660 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6274 2.0000 -4.1585 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4555 3.9877 -3.0947 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8632 1.4137 0.4828 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0137 0.3376 -0.2371 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0906 0.7173 -1.3134 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2270 -0.0787 -1.3660 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7464 -0.0760 -0.0056 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7979 1.2911 0.5753 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7278 -0.8519 -2.0132 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4151 -0.4000 -1.9136 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1261 0.8790 -2.2013 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0438 1.1674 0.0200 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8394 -1.2850 0.2025 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4678 -0.2649 1.6074 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4743 1.0084 -0.9828 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1133 1.7213 0.6318 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8796 0.6041 1.7647 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0889 0.4308 1.8353 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5079 -0.9214 0.6374 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9469 0.7974 0.3143 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9155 -0.1578 -3.1388 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1505 -1.7551 -0.0995 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3633 -1.6737 2.2657 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4937 0.0683 2.3120 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0707 0.2433 2.5863 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1877 -1.5084 2.8774 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6056 -3.0494 1.1592 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3953 -2.7873 -0.3938 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0950 -2.7992 1.2228 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9913 -0.6602 1.6907 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5610 -2.7308 0.9812 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6179 -2.6323 -0.5267 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3250 -1.8390 -1.7336 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2621 -2.6858 -0.4917 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1010 -0.6347 -1.1540 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1968 -0.2901 2.6739 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7137 -1.1158 2.8613 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3752 -2.1108 2.3688 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5012 1.4047 1.0806 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9199 0.4694 0.3279 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6252 0.4332 2.0631 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8492 -2.6424 0.8362 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5719 0.6203 -2.6799 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0530 2.1862 -1.9257 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9189 1.0773 -1.7476 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2884 2.5746 -0.9855 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2579 4.5609 -3.9044 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4703 2.4280 0.2152 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9331 1.3441 1.5791 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8932 1.8005 -1.3608 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5761 0.4728 -2.3066 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8264 0.4310 -2.1507 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0408 -1.0870 -1.6924 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5969 1.4926 1.3109 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1176 1.6291 1.0840 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9679 2.0180 -0.2728 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 2 0 6 7 1 0 6 8 1 0 8 9 2 0 8 10 1 0 2 11 1 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 20 21 1 0 20 22 1 0 20 23 1 0 19 24 1 0 24 25 1 6 25 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 24 30 1 0 31 30 1 1 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 1 34 11 1 0 34 14 1 0 31 16 1 0 31 24 1 0 1 36 1 0 1 37 1 0 1 38 1 0 2 39 1 6 3 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 5 44 1 0 7 45 1 0 7 46 1 0 7 47 1 0 10 48 1 0 11 49 1 6 12 50 1 0 12 51 1 0 13 52 1 0 13 53 1 0 15 54 1 0 15 55 1 0 15 56 1 0 16 57 1 1 17 58 1 0 17 59 1 0 18 60 1 0 18 61 1 0 19 62 1 6 21 63 1 0 21 64 1 0 21 65 1 0 22 66 1 0 22 67 1 0 22 68 1 0 23 69 1 0 25 70 1 0 25 71 1 0 26 72 1 0 26 73 1 0 29 74 1 0 30 75 1 0 30 76 1 0 32 77 1 0 32 78 1 0 33 79 1 0 33 80 1 0 35 81 1 0 35 82 1 0 35 83 1 0 M END

Standard InCHIKey	YLZNPKONASUZEQ-RRKDZSPHSA-N
Standard InCHI	InChI=1S/C30H48O5/c1-19(8-7-9-20(2)25(33)34)21-12-14-28(6)23-11-10-22(26(3,4)35)29(15-13-24(31)32)18-30(23,29)17-16-27(21,28)5/h9,19,21-23,35H,7-8,10-18H2,1-6H3,(H,31,32)(H,33,34)/b20-9-/t19-,21-,22+,23+,27-,28+,29-,30+/m1/s1
SMILES	C[C@H](CC/C=C(/C)C(=O)O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H](C(C)(C)O)[C@@]4(CCC(=O)O)C[C@@]34CC[C@]12C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.35	Volume:	529.252 ? Van der Waals volume.
Dense:	0.923	LogP:	4.101 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.002 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.564 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	20.0
TPSA:	94.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.314	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.357	Fsp³:	0.867
MCE-18:	119.0 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.504	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.505	Promiscuous compounds:	0.237

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.444	MDCK Permeability:	-5.006
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.999 ? 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%):	0.002	30% Bioavailability (F30%):	0.006
50% Bioavailability (F50%):	0.245

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.889
Plasma Protein Binding (PPB):	92.915%	Volume Distribution (VD):	-0.641
Fu:	8.35% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.99	BCRP inhibitor:	0.008
BSEP inhibitor:	0.014

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.995	CYP2C19-substrate:	0.011
CYP2C9-inhibitor:	0.123	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.994	CYP3A4-substrate:	0.987
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.872
HLM stability:	0.062 ? 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):

1.177

Half-life (T1/2):

1.438

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.014
Human Hepatotoxicity (H-HT):	0.67	Drug-induced Liver Injury (DILI):	0.381
AMES Toxicity:	0.092	Rat Oral Acute Toxicity:	0.17
Maximum Recommended Daily Dose:	0.145	Skin Sensitization:	0.704
Carcinogencity:	0.392	Eye Corrosion:	0.004
Eye Irritation:	0.262	Respiratory Toxicity:	0.768
Drug-induced Neurotoxicity:	0.014	Ototoxicity:	0.862
Hematotoxicity:	0.741	Drug-induced Nephrotoxicity:	0.873
Genotoxicity:	0.858	RPMI-8226 Immunitoxicity:	0.019
A549 Cytotoxicity:	0.001	Hek293 Cytotoxicity:	0.01
BCF:	0.745 ? 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:	4.125 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.685 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.387 ? 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
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[15787482]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[15787482]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[15901155]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[15901155]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499331]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643044]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	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
EC50	1
CC50	1

Activity Type	# Activity
Cell line	1
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
NPT1452	Cell line	C8166	Homo sapiens	CC50	=	104.9	ug.mL-1	PMID[19093848]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	16.2	ug.mL-1	PMID[26697718]

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 NPC117122 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	27871
0.1-0.2	19586
0.2-0.3	2080
0.3-0.4	199
0.4-0.5	88
0.5-0.6	19
0.6-0.7	10
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
0.7797	Intermediate Similarity	NPC236618
0.7541	Intermediate Similarity	NPC186975
0.7097	Intermediate Similarity	NPC321690
0.7049	Intermediate Similarity	NPC110923
0.7049	Intermediate Similarity	NPC74296
0.6515	Remote Similarity	NPC29152
0.6406	Remote Similarity	NPC16287
0.6212	Remote Similarity	NPC181743
0.6212	Remote Similarity	NPC178025
0.6061	Remote Similarity	NPC195366
0.6061	Remote Similarity	NPC114743
0.6029	Remote Similarity	NPC194937
0.6029	Remote Similarity	NPC66344
0.6029	Remote Similarity	NPC476038
0.6	Remote Similarity	NPC158846
0.597	Remote Similarity	NPC488282
0.5797	Remote Similarity	NPC23217
0.5735	Remote Similarity	NPC162481
0.5714	Remote Similarity	NPC156546
0.5714	Remote Similarity	NPC475007
0.5652	Remote Similarity	NPC128496
0.5588	Remote Similarity	NPC479654
0.5588	Remote Similarity	NPC479656
0.5541	Remote Similarity	NPC470113
0.5522	Remote Similarity	NPC476186
0.5417	Remote Similarity	NPC479657
0.5362	Remote Similarity	NPC85379
0.5362	Remote Similarity	NPC144909
0.5362	Remote Similarity	NPC476304
0.5352	Remote Similarity	NPC488976
0.5278	Remote Similarity	NPC482629
0.5205	Remote Similarity	NPC479655
0.5139	Remote Similarity	NPC479653
0.507	Remote Similarity	NPC488286

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC117122 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6877
0.1-0.2	2187
0.2-0.3	82
0.3-0.4	4
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