NPASS Compound

Natural Product: NPC520706

Natural Product ID	NPC520706
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(+)-O,O-Dimethylcocsulinine
IUPAC Name	(14~{S})-9,20,25-trimethoxy-15,30-dimethyl-7,23,33-trioxa-15,30-diazaoctacyclo[19.9.3.2^{3,6}.1^{8,12}.1^{14,18}.0^{24,32}.0^{27,31}.0^{22,34}]heptatriaconta-3,5,8(35),9,11,18,20,22(34),24(32),25,27(31),36-dodecaene
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 90 0 0 0 0 0 0 0 0999 V2000 4.7150 -0.2842 3.9479 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2907 -0.4020 2.6090 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2687 -1.2237 2.1842 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5875 -2.0012 3.1064 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5705 -2.8170 2.6645 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2269 -2.8638 1.3020 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9246 -2.0784 0.4184 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9336 -1.2677 0.8616 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6679 -0.4351 -0.0261 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9301 0.6485 -0.5433 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4221 1.5794 0.3434 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6753 2.6190 -0.1632 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4392 2.7306 -1.4983 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9602 1.8076 -2.3645 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7083 0.7623 -1.8811 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4421 3.7226 -2.0226 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5363 4.0981 -0.9779 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0287 3.0527 -0.0686 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3861 3.5884 1.2015 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6849 2.7719 2.2276 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6493 1.3591 2.0541 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9334 0.5917 3.0534 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2198 -0.1264 4.0623 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2987 0.8857 0.7763 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0069 1.7355 -0.2383 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6955 1.1255 -1.4605 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6604 -0.2212 -1.6718 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3583 -0.8156 -2.8767 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0673 -0.0468 -3.9747 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2392 -0.6365 -5.2050 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3411 -2.1870 -3.0155 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6291 -3.0025 -1.9324 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6472 -4.4673 -2.0440 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4334 -5.1247 -0.9830 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0357 -4.3239 0.0313 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4085 -5.0860 1.2056 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1486 -3.2500 0.4876 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1533 -3.7954 0.9483 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9294 -2.4050 -0.7296 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9473 -1.0485 -0.6162 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2753 -0.4858 0.6324 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4753 5.0985 1.2401 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0969 5.5761 -0.0376 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5025 5.1030 -1.2416 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3851 4.8797 -2.3360 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3100 0.6520 4.1068 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8766 -0.2524 4.6714 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3962 -1.1549 4.1712 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8094 -2.0055 4.1640 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0193 -3.4387 3.3817 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7193 -2.0746 -0.6318 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6264 1.4603 1.3848 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3150 3.3337 0.5308 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7843 1.9030 -3.4134 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1138 0.0414 -2.5568 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9943 4.6069 -2.3559 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1039 3.2163 -2.8473 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1983 4.7210 -0.2514 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9587 3.1803 3.2075 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4486 -1.2153 3.7633 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4414 -0.2005 4.8909 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1968 0.2069 4.5754 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2391 -1.1331 -5.2086 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2352 0.1600 -5.9790 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5070 -1.4084 -5.5089 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1057 -2.6723 -3.9595 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1714 -4.7368 -3.0337 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3823 -4.8979 -2.0893 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7644 -5.8563 -0.4537 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2851 -5.7514 -1.4086 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4583 -5.4117 1.1831 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7777 -6.0058 1.3157 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2517 -4.5108 2.1451 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6733 -2.6414 1.2270 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5974 -4.5042 0.1894 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0680 -4.5039 1.8124 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0947 5.3976 2.1172 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4956 5.5647 1.3712 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1748 5.2899 0.0104 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0835 6.6853 -0.0583 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4011 4.6378 -1.9603 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0539 4.1269 -3.0514 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4756 5.8518 -2.9004 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 13 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 21 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 1 0 28 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 37 39 1 0 39 40 2 0 40 41 1 0 19 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 8 3 1 0 15 10 1 0 44 17 1 0 38 6 1 0 25 18 1 0 40 27 1 0 41 24 1 0 39 32 1 0 1 46 1 0 1 47 1 0 1 48 1 0 4 49 1 0 5 50 1 0 7 51 1 0 11 52 1 0 12 53 1 0 14 54 1 0 15 55 1 0 16 56 1 0 16 57 1 0 17 58 1 0 20 59 1 0 23 60 1 0 23 61 1 0 23 62 1 0 30 63 1 0 30 64 1 0 30 65 1 0 31 66 1 0 33 67 1 0 33 68 1 0 34 69 1 0 34 70 1 0 36 71 1 0 36 72 1 0 36 73 1 0 37 74 1 1 38 75 1 0 38 76 1 0 42 77 1 0 42 78 1 0 43 79 1 0 43 80 1 0 45 81 1 0 45 82 1 0 45 83 1 0 M END

Standard InCHIKey	LJPRYJYATIYRAB-GEVKEYJPSA-N
Standard InCHI	InChI=1S/C37H38N2O6/c1-38-14-12-23-19-30(41-4)34-36-32(23)26(38)16-21-6-9-25(10-7-21)43-29-18-22(8-11-28(29)40-3)17-27-33-24(13-15-39(27)2)20-31(42-5)35(44-36)37(33)45-34/h6-11,18-20,26-27H,12-17H2,1-5H3/t26?,27-/m0/s1
SMILES	COC1=CC=C2C=C1OC1=CC=C(C=C1)CC1C3=C(C=C(OC)C4=C3OC3=C(OC)C=C5CCN(C)[C@@H](C2)C5=C3O4)CCN1C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	606.27	Volume:	623.154 ? Van der Waals volume.
Dense:	0.973	LogP:	3.747 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.476 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.251 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	44.0
TPSA:	61.86 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	0.0	Rings:	10.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.213	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.136	Fsp³:	0.351
MCE-18:	142.76 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.982	Fluc inhibitor:	0.025 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.898 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.967 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.231

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.837	MDCK Permeability:	-4.717
Pgp-inhibitor:	0.309	Pgp-substrate:	0.783
PAMPA:	0.018 ? 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):	0.0
20% Bioavailability (F20%):	0.119	30% Bioavailability (F30%):	0.742
50% Bioavailability (F50%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.98	MRP1:	0.97
Plasma Protein Binding (PPB):	77.016%	Volume Distribution (VD):	0.334
Fu:	21.851% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.298
OATP1B3 inhibitor:	0.244	BCRP inhibitor:	0.501
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.927	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.692
CYP2B6-substrate:	0.914	CYP2C8-inhibitor:	0.094
HLM stability:	0.515 ? 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):

8.293

Half-life (T1/2):

3.301

ADMET: Toxicity

hERG Blockers:	0.894	hERG Blockers (10um):	0.845
Human Hepatotoxicity (H-HT):	0.602	Drug-induced Liver Injury (DILI):	0.01
AMES Toxicity:	0.714	Rat Oral Acute Toxicity:	0.809
Maximum Recommended Daily Dose:	0.963	Skin Sensitization:	0.797
Carcinogencity:	0.895	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.873
Drug-induced Neurotoxicity:	0.788	Ototoxicity:	0.775
Hematotoxicity:	0.118	Drug-induced Nephrotoxicity:	0.147
Genotoxicity:	0.385	RPMI-8226 Immunitoxicity:	0.083
A549 Cytotoxicity:	0.232	Hek293 Cytotoxicity:	0.779
BCF:	2.087 ? 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:	4.765 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.087 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.643 ? 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
NPO42831	Cocculus pendulus (Forsk.) Diels	Genus	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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

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

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 NPC520706 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	32841
0.1-0.2	16104
0.2-0.3	644
0.3-0.4	133
0.4-0.5	47
0.5-0.6	38
0.6-0.7	31
0.7-0.8	2
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.871	High Similarity	NPC41376
0.8438	Intermediate Similarity	NPC12424
0.8438	Intermediate Similarity	NPC129518
0.8438	Intermediate Similarity	NPC251580
0.7692	Intermediate Similarity	NPC76682
0.7692	Intermediate Similarity	NPC10908
0.7692	Intermediate Similarity	NPC63646
0.7692	Intermediate Similarity	NPC317145
0.7692	Intermediate Similarity	NPC198498
0.7692	Intermediate Similarity	NPC115284
0.7576	Intermediate Similarity	NPC276890
0.7463	Intermediate Similarity	NPC227060
0.7458	Intermediate Similarity	NPC317439
0.7377	Intermediate Similarity	NPC247639
0.7377	Intermediate Similarity	NPC25084
0.7143	Intermediate Similarity	NPC73492
0.7143	Intermediate Similarity	NPC299990
0.7067	Intermediate Similarity	NPC249996
0.6901	Remote Similarity	NPC480587
0.6761	Remote Similarity	NPC603853
0.6712	Remote Similarity	NPC311973
0.6667	Remote Similarity	NPC290582
0.6667	Remote Similarity	NPC217748
0.6667	Remote Similarity	NPC182052
0.6667	Remote Similarity	NPC271013
0.6667	Remote Similarity	NPC42663
0.6667	Remote Similarity	NPC15414
0.6575	Remote Similarity	NPC279228
0.6533	Remote Similarity	NPC274716
0.6533	Remote Similarity	NPC167116
0.6533	Remote Similarity	NPC609821
0.6486	Remote Similarity	NPC239824
0.641	Remote Similarity	NPC485712
0.64	Remote Similarity	NPC254441
0.64	Remote Similarity	NPC116465
0.6316	Remote Similarity	NPC229373
0.6282	Remote Similarity	NPC475479
0.6282	Remote Similarity	NPC323537
0.625	Remote Similarity	NPC603603
0.6184	Remote Similarity	NPC185639
0.6184	Remote Similarity	NPC251735
0.6184	Remote Similarity	NPC49075
0.6184	Remote Similarity	NPC223690
0.6184	Remote Similarity	NPC9532
0.6184	Remote Similarity	NPC599951
0.6061	Remote Similarity	NPC104196
0.6049	Remote Similarity	NPC10871
0.6024	Remote Similarity	NPC485711
0.6	Remote Similarity	NPC30779
0.5904	Remote Similarity	NPC281581
0.5854	Remote Similarity	NPC239584
0.5802	Remote Similarity	NPC24260
0.5698	Remote Similarity	NPC85381
0.5641	Remote Similarity	NPC475393
0.5641	Remote Similarity	NPC286119
0.5625	Remote Similarity	NPC181796
0.5625	Remote Similarity	NPC290005
0.5625	Remote Similarity	NPC54654
0.5625	Remote Similarity	NPC7715
0.5625	Remote Similarity	NPC328155
0.5625	Remote Similarity	NPC222661
0.5625	Remote Similarity	NPC285931
0.5595	Remote Similarity	NPC480590
0.5556	Remote Similarity	NPC195538
0.5529	Remote Similarity	NPC11296
0.5529	Remote Similarity	NPC274661
0.5517	Remote Similarity	NPC475597
0.5488	Remote Similarity	NPC139783
0.5488	Remote Similarity	NPC65312
0.5488	Remote Similarity	NPC212237
0.5488	Remote Similarity	NPC243454
0.5488	Remote Similarity	NPC611798
0.5455	Remote Similarity	NPC191132
0.5422	Remote Similarity	NPC611658
0.5417	Remote Similarity	NPC317272
0.5417	Remote Similarity	NPC268503
0.5412	Remote Similarity	NPC480586
0.5397	Remote Similarity	NPC213206
0.5397	Remote Similarity	NPC188163
0.5397	Remote Similarity	NPC328750
0.5238	Remote Similarity	NPC8836
0.5238	Remote Similarity	NPC314682
0.5181	Remote Similarity	NPC16357
0.5181	Remote Similarity	NPC302245
0.5172	Remote Similarity	NPC254581
0.5132	Remote Similarity	NPC480592
0.5062	Remote Similarity	NPC112248

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC520706 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4718
0.1-0.2	4267
0.2-0.3	147
0.3-0.4	12
0.4-0.5	2
0.5-0.6	1
0.6-0.7	1
0.7-0.8	2
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
0.7692	Intermediate Similarity	NPD8099	Discontinued
0.7246	Intermediate Similarity	NPD8156	Discontinued
0.6667	Remote Similarity	NPD8095	Phase 1
0.5397	Remote Similarity	NPD4664	Clinical (unspecified phase)

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