NPASS Compound

Natural Product: NPC197037

Natural Product ID	NPC197037
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UEDMLPVUDFCAQM-IWVNULRZSA-N
IUPAC Name	n.a.
Synonyms	7-epi-10-oxo-10-DAB
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL250045
PubChem CID	5316369
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

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 73 77 0 0 0 0 0 0 0 0999 V2000 -4.7593 -0.3112 -1.4947 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4441 -0.8434 -1.4862 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8366 -1.0908 -0.3059 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3085 -0.0338 0.5667 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5021 0.1360 0.3846 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6097 0.8236 1.5788 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4249 1.3445 2.2998 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1243 1.0812 1.7700 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7013 0.3406 2.9770 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0701 2.5421 2.1918 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9838 3.4488 1.0138 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4415 3.2254 0.5394 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7466 1.8161 0.2646 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7302 1.9374 1.3948 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3063 3.2229 1.6303 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3774 0.8148 0.4760 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0399 -0.5613 0.1669 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6318 -1.4330 -0.8479 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0571 -0.9009 -2.1439 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4953 -1.1691 -2.6278 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8239 -0.1786 -3.5931 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8633 -2.1795 -0.2184 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1953 -3.4145 -1.0195 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6233 -2.6301 1.1708 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1958 -2.5337 -1.0571 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 -0.5493 0.0131 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3956 -1.1699 0.7556 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9611 -1.8573 1.7107 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8203 -1.1029 0.5384 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6739 -1.7806 1.3668 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0400 -1.7182 1.1604 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5402 -0.9755 0.1234 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7082 -0.2832 -0.7262 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3351 -0.3627 -0.4966 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4514 1.7278 -0.9322 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0759 2.1667 -2.1698 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0559 2.7353 -2.2487 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9540 1.9827 -3.3525 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1083 2.8641 3.0449 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9528 0.7764 -1.6542 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6287 -0.9382 -1.1886 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0003 -0.5082 -2.6081 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3645 1.0067 3.8412 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5813 -0.1864 3.4706 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0704 -0.4051 2.9111 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1488 2.6600 2.8013 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0764 4.4826 1.3500 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7307 3.1456 0.2687 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7517 3.9957 -0.1807 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 1.9795 1.0726 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6678 1.2243 2.2130 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1302 1.1111 -0.3219 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0788 -1.1600 1.0925 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9620 0.1881 -2.2706 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4543 -1.3310 -3.0044 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6663 -2.0881 -3.1218 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4115 -0.4796 -4.4539 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0705 -4.3616 -0.3923 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4514 -3.6219 -1.8340 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2468 -3.4856 -1.3325 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0597 -1.8897 1.8674 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6455 -3.0263 1.4237 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3126 -3.5260 1.3483 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1159 -3.2600 -0.4309 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2981 -2.3813 2.2029 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6713 -2.2710 1.8420 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6334 -0.9515 -0.0070 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1396 0.2862 -1.5256 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7203 0.1988 -1.1915 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6360 2.6391 -4.1709 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9856 2.3205 -3.0674 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9385 0.9040 -3.6123 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3349 3.8221 2.9992 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 4 6 1 0 6 7 2 0 6 8 1 0 8 9 1 1 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 13 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 18 22 1 0 22 23 1 0 22 24 1 0 18 25 1 6 17 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 13 35 1 6 35 36 1 0 36 37 2 0 36 38 1 0 10 39 1 0 20 2 1 0 34 29 1 0 22 3 1 0 16 8 1 0 15 12 1 0 1 40 1 0 1 41 1 0 1 42 1 0 9 43 1 0 9 44 1 0 9 45 1 0 10 46 1 1 11 47 1 0 11 48 1 0 12 49 1 6 14 50 1 0 14 51 1 0 16 52 1 6 17 53 1 1 19 54 1 0 19 55 1 0 20 56 1 6 21 57 1 0 23 58 1 0 23 59 1 0 23 60 1 0 24 61 1 0 24 62 1 0 24 63 1 0 25 64 1 0 30 65 1 0 31 66 1 0 32 67 1 0 33 68 1 0 34 69 1 0 38 70 1 0 38 71 1 0 38 72 1 0 39 73 1 0 M END

Standard InCHIKey	UEDMLPVUDFCAQM-IWVNULRZSA-N
Standard InCHI	InChI=1S/C29H34O10/c1-14-17(31)12-29(36)24(38-25(35)16-9-7-6-8-10-16)22-27(5,23(34)21(33)20(14)26(29,3)4)18(32)11-19-28(22,13-37-19)39-15(2)30/h6-10,17-19,22,24,31-32,36H,11-13H2,1-5H3/t17-,18+,19+,22-,24-,27+,28-,29+/m0/s1
SMILES	CC1=C2C(=O)C(=O)[C@]3(C)[C@@H](C[C@@H]4[C@@](CO4)([C@H]3[C@@H]([C@](C[C@@H]1O)(C2(C)C)O)OC(=O)c1ccccc1)OC(=O)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	542.22	Volume:	534.168 ? Van der Waals volume.
Dense:	1.015	LogP:	1.44 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.868 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.636 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	30.0
TPSA:	156.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.376	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.408	Fsp³:	0.586
MCE-18:	137.348 ? 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:	1
Colloidal aggregators:	0.588	Fluc inhibitor:	0.086 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.007 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.056	Promiscuous compounds:	0.301

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.371	MDCK Permeability:	-4.78
Pgp-inhibitor:	0.849	Pgp-substrate:	0.998
PAMPA:	0.993 ? 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):	0.003
20% Bioavailability (F20%):	0.516	30% Bioavailability (F30%):	0.954
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.996
Plasma Protein Binding (PPB):	90.746%	Volume Distribution (VD):	0.105
Fu:	8.621% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.017
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.031	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.938
HLM stability:	0.422 ? 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):

9.064

Half-life (T1/2):

2.632

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.107
Human Hepatotoxicity (H-HT):	0.612	Drug-induced Liver Injury (DILI):	0.622
AMES Toxicity:	0.797	Rat Oral Acute Toxicity:	0.316
Maximum Recommended Daily Dose:	0.662	Skin Sensitization:	0.939
Carcinogencity:	0.598	Eye Corrosion:	0.0
Eye Irritation:	0.128	Respiratory Toxicity:	0.18
Drug-induced Neurotoxicity:	0.047	Ototoxicity:	0.745
Hematotoxicity:	0.752	Drug-induced Nephrotoxicity:	0.939
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.149
A549 Cytotoxicity:	0.048	Hek293 Cytotoxicity:	0.246
BCF:	0.47 ? 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:	3.174 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.862 ? 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
NPO23229	Cochliobolus lunatus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027752]
NPO32766	luteibacter sp.	Species	Rhodanobacteraceae	Bacteria	n.a.	n.a.	n.a.	PMID[18001087]
NPO23229	Cochliobolus lunatus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20527910]
NPO23229	Cochliobolus lunatus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9014347]
NPO23229	Cochliobolus lunatus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23229	Cochliobolus lunatus	Species	Pleosporaceae	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	7
ID50	1

Activity Type	# Activity
Cell line	7
Others	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
NPT180	Cell line	HCT-8	Homo sapiens	IC50	<	10000.0	nM	PMID[20102168]
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	<	10000.0	nM	PMID[11473426]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	=	1380.0	nM	Open TG-GATES in vivo data: Organ Weight
NPT81	Cell line	A549	Homo sapiens	IC50	<	10000.0	nM	Open TG-GATES in vivo data: Organ Weight
NPT179	Cell line	A2780	Homo sapiens	IC50	=	4890.0	nM	PMID[12502361]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	60000.0	nM	PMID[15497961]
NPT2	Others	Unspecified	n.a.	ID50	>	100.0	uM	PMID[15104485]

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 NPC197037 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	7341
0.1-0.2	38958
0.2-0.3	3063
0.3-0.4	427
0.4-0.5	18
0.5-0.6	36
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8133	Intermediate Similarity	NPC91730
0.7692	Intermediate Similarity	NPC155329
0.7692	Intermediate Similarity	NPC114357
0.7662	Intermediate Similarity	NPC229545
0.7662	Intermediate Similarity	NPC134685
0.6867	Remote Similarity	NPC259144
0.6829	Remote Similarity	NPC11588
0.6585	Remote Similarity	NPC248265
0.6224	Remote Similarity	NPC478329
0.6186	Remote Similarity	NPC191193
0.6118	Remote Similarity	NPC217918
0.6071	Remote Similarity	NPC38696
0.6	Remote Similarity	NPC609501
0.593	Remote Similarity	NPC605573
0.5909	Remote Similarity	NPC219419
0.5806	Remote Similarity	NPC603140
0.5521	Remote Similarity	NPC471493
0.5347	Remote Similarity	NPC473300
0.5347	Remote Similarity	NPC36607
0.534	Remote Similarity	NPC33372
0.534	Remote Similarity	NPC67246
0.5288	Remote Similarity	NPC487360
0.5288	Remote Similarity	NPC479182
0.5288	Remote Similarity	NPC479180
0.5281	Remote Similarity	NPC92867
0.5243	Remote Similarity	NPC471623
0.5243	Remote Similarity	NPC453583
0.5243	Remote Similarity	NPC208553
0.5243	Remote Similarity	NPC181964
0.5243	Remote Similarity	NPC307628
0.5243	Remote Similarity	NPC473400
0.5243	Remote Similarity	NPC603171
0.5192	Remote Similarity	NPC479183
0.5192	Remote Similarity	NPC324251
0.5192	Remote Similarity	NPC206211
0.5192	Remote Similarity	NPC479181
0.5169	Remote Similarity	NPC132599
0.5146	Remote Similarity	NPC321072
0.5146	Remote Similarity	NPC215892
0.5146	Remote Similarity	NPC242662
0.5146	Remote Similarity	NPC102167
0.5146	Remote Similarity	NPC488127
0.5143	Remote Similarity	NPC471629
0.5143	Remote Similarity	NPC306001
0.5096	Remote Similarity	NPC317882
0.5093	Remote Similarity	NPC487361
0.5048	Remote Similarity	NPC471754
0.5047	Remote Similarity	NPC471606
0.5047	Remote Similarity	NPC275170

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC197037 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3048
0.1-0.2	5920
0.2-0.3	168
0.3-0.4	3
0.4-0.5	8
0.5-0.6	3
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
0.5243	Remote Similarity	NPD8485	Phase 4
0.5146	Remote Similarity	NPD8360	Approved
0.5146	Remote Similarity	NPD8361	Phase 4

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