NPASS Compound

Natural Product: NPC111214

Natural Product ID	NPC111214
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Bartogenic Acid
IUPAC Name	(2R,3R,4S,4aR,6aR,6bS,8aR,12S,12aS,14aR,14bR)-2,3,12-trihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid
Synonyms	Bartogenic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL551967
PubChem CID	45272347
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 87 0 0 0 0 0 0 0 0999 V2000 -4.7215 1.8582 -2.9381 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5262 1.5618 -1.5670 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0498 1.5642 -1.3487 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6629 1.0002 0.0274 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1322 1.9761 1.0341 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2447 -0.3675 0.1108 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7403 -0.4593 -0.0647 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1951 0.2667 -1.3035 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5764 0.4845 -1.1664 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5521 -0.0099 1.0811 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0216 -1.8995 -0.3164 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7672 -2.5217 0.4710 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4917 -2.5922 -1.3927 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7700 -1.1818 1.2617 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5054 -0.8082 1.8982 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6062 0.1578 1.2297 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1764 0.7971 -0.0226 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3818 1.9694 -0.4505 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0434 1.5543 -0.5364 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5569 0.4618 0.0289 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7404 -0.4874 0.8283 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4048 -1.6502 -0.0833 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3964 -0.9344 2.0890 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8797 -0.9307 2.1118 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5893 -0.0248 1.1898 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9955 0.2007 -0.1517 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3536 -0.8926 -1.1051 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3452 -2.1673 -0.5525 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8289 -0.6640 -1.4920 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4755 -1.9798 -1.8709 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9500 0.2777 -2.6547 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5934 -0.1116 -0.3094 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0195 -0.5725 1.0018 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8134 1.3312 1.8104 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4553 1.6059 2.9828 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4358 2.3420 1.0920 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2249 1.2454 2.2279 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9105 2.1556 -3.3781 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0551 2.4068 -1.0372 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5768 0.9815 -2.1639 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7057 2.6204 -1.3409 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6358 2.9564 0.8057 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0941 1.6814 2.0740 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2178 2.1931 0.8063 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8464 -0.8848 -0.8221 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0821 -0.3825 -2.2061 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0851 -0.3627 -1.1375 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0357 0.2795 1.9893 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2124 0.8655 0.8045 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3080 -0.7899 1.4046 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0762 -3.3182 -1.8346 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7952 -2.2700 0.9410 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6064 -1.1669 2.0273 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6932 -0.5027 2.9751 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9126 -1.7649 2.0448 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0157 0.0233 -0.8377 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5279 2.8845 0.1428 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7060 2.2402 -1.4985 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7518 2.1810 -1.1066 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8164 -2.5971 0.3781 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6867 -1.8467 -0.1218 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7337 -1.5407 -1.1126 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0231 -0.4154 3.0003 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0774 -2.0064 2.2726 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2540 -0.6868 3.1531 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2934 -1.9708 1.9413 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5237 1.1212 -0.5609 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8058 -0.8167 -2.0494 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1941 -2.8022 -1.2999 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2274 -2.7568 -1.1180 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5834 -1.8276 -1.7908 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1794 -2.3151 -2.8792 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9862 0.8088 -2.7625 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8015 0.9807 -2.5372 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1286 -0.2911 -3.5914 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6800 0.9901 -0.3469 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6293 -0.5011 -0.3652 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6812 -0.1982 1.8025 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0241 -1.6722 1.0497 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2755 3.3337 1.2845 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4968 0.9258 3.2775 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7555 2.1894 2.0656 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8366 1.4692 2.2388 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 1 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 7 10 1 1 7 11 1 0 11 12 2 0 11 13 1 0 6 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 29 31 1 0 29 32 1 0 32 33 1 0 25 34 1 1 34 35 2 0 34 36 1 0 16 37 1 1 8 2 1 0 21 16 1 0 33 25 1 0 17 4 1 0 26 20 1 0 1 38 1 0 2 39 1 1 3 40 1 0 3 41 1 0 5 42 1 0 5 43 1 0 5 44 1 0 6 45 1 6 8 46 1 6 9 47 1 0 10 48 1 0 10 49 1 0 10 50 1 0 13 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 17 56 1 6 18 57 1 0 18 58 1 0 19 59 1 0 22 60 1 0 22 61 1 0 22 62 1 0 23 63 1 0 23 64 1 0 24 65 1 0 24 66 1 0 26 67 1 6 27 68 1 6 28 69 1 0 30 70 1 0 30 71 1 0 30 72 1 0 31 73 1 0 31 74 1 0 31 75 1 0 32 76 1 0 32 77 1 0 33 78 1 0 33 79 1 0 36 80 1 0 37 81 1 0 37 82 1 0 37 83 1 0 M END

Standard InCHIKey	BBJQJXRZAZWPBL-SOTYDYGCSA-N
Standard InCHI	InChI=1S/C30H46O7/c1-25(2)11-13-30(24(36)37)14-12-27(4)16(20(30)22(25)33)7-8-18-26(3)15-17(31)21(32)29(6,23(34)35)19(26)9-10-28(18,27)5/h7,17-22,31-33H,8-15H2,1-6H3,(H,34,35)(H,36,37)/t17-,18-,19-,20-,21+,22+,26-,27-,28-,29+,30+/m1/s1
SMILES	O[C@@H]1C[C@@]2(C)[C@H]([C@]([C@H]1O)(C)C(=O)O)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@H](O)C(C)(C)CC1)C(=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	518.32	Volume:	538.276 ? Van der Waals volume.
Dense:	0.963	LogP:	2.399 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.374 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.854 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	135.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.345	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.112	Fsp³:	0.867
MCE-18:	114.0 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.712	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.273 ? 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:	0.084

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.717	MDCK Permeability:	-5.18
Pgp-inhibitor:	0.0	Pgp-substrate:	0.026
PAMPA:	1.0 ? 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):	0.005
20% Bioavailability (F20%):	0.146	30% Bioavailability (F30%):	0.031
50% Bioavailability (F50%):	0.743

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024	MRP1:	0.995
Plasma Protein Binding (PPB):	83.153%	Volume Distribution (VD):	-0.304
Fu:	14.472% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.812	BCRP inhibitor:	0.0
BSEP inhibitor:	0.634

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.034
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.008
HLM stability:	0.002 ? 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):

0.866

Half-life (T1/2):

1.719

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.002
Human Hepatotoxicity (H-HT):	0.564	Drug-induced Liver Injury (DILI):	0.761
AMES Toxicity:	0.208	Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.065	Skin Sensitization:	0.965
Carcinogencity:	0.559	Eye Corrosion:	0.004
Eye Irritation:	0.194	Respiratory Toxicity:	0.668
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.878
Hematotoxicity:	0.657	Drug-induced Nephrotoxicity:	0.992
Genotoxicity:	0.804	RPMI-8226 Immunitoxicity:	0.028
A549 Cytotoxicity:	0.026	Hek293 Cytotoxicity:	0.013
BCF:	0.538 ? 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:	3.454 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.002 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.118 ? 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
NPO5697	Barringtonia racemosa	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19388709]
NPO5697	Barringtonia racemosa	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5697	Barringtonia racemosa	Species	Lecythidaceae	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
IC50	2

Activity Type	# Activity
Cell line	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
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[22439863]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[19388709]

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 NPC111214 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	26213
0.1-0.2	20668
0.2-0.3	2401
0.3-0.4	389
0.4-0.5	137
0.5-0.6	37
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
0.7538	Intermediate Similarity	NPC106112
0.7538	Intermediate Similarity	NPC261935
0.7313	Intermediate Similarity	NPC35239
0.7273	Intermediate Similarity	NPC173744
0.7273	Intermediate Similarity	NPC204961
0.7273	Intermediate Similarity	NPC73004
0.6818	Remote Similarity	NPC43686
0.6716	Remote Similarity	NPC187722
0.6618	Remote Similarity	NPC229281
0.6522	Remote Similarity	NPC38754
0.6522	Remote Similarity	NPC271614
0.6377	Remote Similarity	NPC194196
0.6056	Remote Similarity	NPC73489
0.5694	Remote Similarity	NPC282616
0.5676	Remote Similarity	NPC132824
0.5616	Remote Similarity	NPC472149
0.5616	Remote Similarity	NPC609452
0.5556	Remote Similarity	NPC96916
0.5526	Remote Similarity	NPC174663
0.5479	Remote Similarity	NPC84319
0.5479	Remote Similarity	NPC52021
0.5479	Remote Similarity	NPC599947
0.5405	Remote Similarity	NPC231063
0.5405	Remote Similarity	NPC282395
0.5405	Remote Similarity	NPC88116
0.5405	Remote Similarity	NPC71074
0.5405	Remote Similarity	NPC37221
0.5405	Remote Similarity	NPC481360
0.5405	Remote Similarity	NPC110308
0.5405	Remote Similarity	NPC605937
0.5395	Remote Similarity	NPC607666
0.5395	Remote Similarity	NPC608261
0.5395	Remote Similarity	NPC611078
0.5333	Remote Similarity	NPC259733
0.5333	Remote Similarity	NPC158371
0.5333	Remote Similarity	NPC207922
0.5333	Remote Similarity	NPC87095
0.5333	Remote Similarity	NPC32407
0.5333	Remote Similarity	NPC263548
0.5333	Remote Similarity	NPC606320
0.5263	Remote Similarity	NPC247139
0.5195	Remote Similarity	NPC25299
0.5195	Remote Similarity	NPC481322
0.5128	Remote Similarity	NPC20235
0.5128	Remote Similarity	NPC299996
0.5067	Remote Similarity	NPC182797
0.5067	Remote Similarity	NPC121798
0.5067	Remote Similarity	NPC234346
0.5067	Remote Similarity	NPC52169
0.5067	Remote Similarity	NPC488562

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC111214 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6735
0.1-0.2	2376
0.2-0.3	36
0.3-0.4	3
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