NPASS Compound

Natural Product: NPC565896

Natural Product ID	NPC565896
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Vernadigin
IUPAC Name	(3~{S},5~{S},8~{R},9~{S},10~{S},13~{R},14~{S},16~{S},17~{R})-5,14,16-trihydroxy-3-[(2~{R},4~{R},5~{S},6~{R})-5-hydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-13-methyl-17-(5-oxo-2~{H}-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1~{H}-cyclopenta[a]phenanthrene-10-carbaldehyde
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 84 89 0 0 0 0 0 0 0 0999 V2000 7.8992 2.2997 0.0853 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9607 1.3180 0.3689 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9352 0.3011 -0.5839 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6375 0.1964 -1.3000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6992 -0.8517 -0.7919 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7419 -0.2793 0.0321 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4514 -0.3522 -0.4888 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5754 -1.1076 0.4798 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9191 -0.1010 1.3821 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0789 0.7269 0.5934 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3345 1.9466 1.4208 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1832 2.1635 2.4911 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3558 -0.0553 0.5014 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1876 0.1873 1.7419 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5601 -0.3731 1.6878 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3582 0.1109 0.4490 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5941 1.5545 0.6492 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5175 -0.7862 0.3107 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6970 -0.2974 -0.4460 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8638 0.8185 -1.0950 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1942 0.8646 -1.6858 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6869 1.8203 -2.3908 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8229 -0.3070 -1.3467 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9797 -1.0787 -0.5472 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9614 -2.0481 -0.2925 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6837 -2.5681 -1.3346 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5218 -1.7241 -0.7237 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5089 -0.2079 -0.7643 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0925 0.1870 -1.9426 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1478 0.3772 -0.6791 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4214 0.0562 -1.9549 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0159 0.4049 -1.9066 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4664 1.1759 -0.7191 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1742 2.5361 -0.9241 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9782 1.0841 -0.6532 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3057 -1.9468 -0.2292 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2571 -1.6420 0.7281 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7207 -0.9157 1.9165 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4030 -0.9685 0.0498 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4315 -0.6961 0.9463 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6590 2.7545 -0.8933 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8444 3.0401 0.9102 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9388 1.8611 0.0358 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7205 0.5822 -1.3466 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1215 1.1961 -1.1957 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7962 0.1057 -2.4147 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1362 -1.2349 -1.6953 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5164 -0.8698 -1.4702 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1634 -1.8335 1.0953 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7813 -1.6961 -0.0072 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7392 0.5721 1.7645 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4328 -0.6497 2.1986 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0314 2.7143 1.0630 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1311 -1.1447 0.4835 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1330 1.2637 2.0606 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6655 -0.3460 2.5950 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1284 0.0170 2.5483 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5294 -1.4588 1.7506 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2325 2.2316 -0.1505 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6303 1.7373 0.9894 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9769 1.8939 1.5475 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8691 -1.0319 1.3867 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1681 1.6681 -1.2425 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8647 -2.0507 -1.0410 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4046 -1.1804 0.4809 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8995 -2.8598 0.4908 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6816 -3.5610 -1.3709 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8187 -2.1660 -0.0233 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3340 -2.1521 -1.7288 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9253 1.1536 -2.1481 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2570 1.4823 -0.6335 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5916 -1.0289 -2.2103 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9725 0.6079 -2.7730 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6046 -0.5302 -2.0942 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2383 1.0419 -2.8148 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0353 2.7326 -1.8762 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3615 1.5250 -1.5893 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3878 1.6997 0.1835 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6424 -2.6355 1.1032 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7931 -1.4335 2.2427 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4602 -0.9927 2.7374 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5037 0.1395 1.7639 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8147 -1.6775 -0.7028 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3667 -1.3094 1.7382 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 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 1 11 12 2 0 10 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 18 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 28 29 1 6 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 6 33 35 1 0 5 36 1 0 36 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 39 3 1 0 35 7 1 0 33 10 1 0 30 13 1 0 28 16 1 0 24 19 1 0 1 41 1 0 1 42 1 0 1 43 1 0 3 44 1 6 4 45 1 0 4 46 1 0 5 47 1 6 7 48 1 6 8 49 1 0 8 50 1 0 9 51 1 0 9 52 1 0 11 53 1 0 13 54 1 6 14 55 1 0 14 56 1 0 15 57 1 0 15 58 1 0 17 59 1 0 17 60 1 0 17 61 1 0 18 62 1 1 20 63 1 0 24 64 1 0 24 65 1 0 25 66 1 1 26 67 1 0 27 68 1 0 27 69 1 0 29 70 1 0 30 71 1 1 31 72 1 0 31 73 1 0 32 74 1 0 32 75 1 0 34 76 1 0 35 77 1 0 35 78 1 0 37 79 1 1 38 80 1 0 38 81 1 0 38 82 1 0 39 83 1 6 40 84 1 0 M END

Standard InCHIKey	NAQIOLFTZRJOKV-OBDZMSMTSA-N
Standard InCHI	InChI=1S/C30H44O10/c1-16-26(34)22(37-3)11-24(39-16)40-18-4-8-28(15-31)19-5-7-27(2)25(17-10-23(33)38-14-17)21(32)13-30(27,36)20(19)6-9-29(28,35)12-18/h10,15-16,18-22,24-26,32,34-36H,4-9,11-14H2,1-3H3/t16-,18+,19+,20-,21+,22-,24+,25+,26+,27-,28+,29+,30+/m1/s1
SMILES	CO[C@@H]1C[C@H](O[C@H]2CC[C@]3(C=O)[C@H]4CC[C@]5(C)[C@@H](C6=CC(=O)OC6)[C@@H](O)C[C@]5(O)[C@@H]4CC[C@]3(O)C2)O[C@H](C)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	564.29	Volume:	556.09 ? Van der Waals volume.
Dense:	1.015	LogP:	1.023 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.55 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.973 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	33.0
TPSA:	151.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.219	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.492	Fsp³:	0.867
MCE-18:	115.679 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.685	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.155	Promiscuous compounds:	0.635

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.71	MDCK Permeability:	-5.187
Pgp-inhibitor:	0.0	Pgp-substrate:	0.902
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):	0.041
20% Bioavailability (F20%):	0.218	30% Bioavailability (F30%):	0.282
50% Bioavailability (F50%):	0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034	MRP1:	0.657
Plasma Protein Binding (PPB):	75.586%	Volume Distribution (VD):	0.134
Fu:	20.147% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.982
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.005
BSEP inhibitor:	0.361

ADMET: Metabolism

CYP1A2-inhibitor:	0.094	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.118	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.533	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.017
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.193
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.766
HLM stability:	0.056 ? 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):

2.47

Half-life (T1/2):

3.677

ADMET: Toxicity

hERG Blockers:	0.069	hERG Blockers (10um):	0.611
Human Hepatotoxicity (H-HT):	0.537	Drug-induced Liver Injury (DILI):	0.783
AMES Toxicity:	0.978	Rat Oral Acute Toxicity:	0.981
Maximum Recommended Daily Dose:	0.998	Skin Sensitization:	1.0
Carcinogencity:	0.961	Eye Corrosion:	0.0
Eye Irritation:	0.018	Respiratory Toxicity:	0.995
Drug-induced Neurotoxicity:	0.139	Ototoxicity:	0.412
Hematotoxicity:	0.76	Drug-induced Nephrotoxicity:	0.956
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.707
A549 Cytotoxicity:	0.864	Hek293 Cytotoxicity:	0.961
BCF:	0.481 ? 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:	3.267 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.001 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.057 ? 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
NPO50497	Adonis vernalis L.	Genus	Ranunculaceae	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 NPC565896 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	15846
0.1-0.2	31149
0.2-0.3	2556
0.3-0.4	159
0.4-0.5	91
0.5-0.6	38
0.6-0.7	16
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
0.8442	Intermediate Similarity	NPC180079
0.7284	Intermediate Similarity	NPC34390
0.7284	Intermediate Similarity	NPC99080
0.7065	Intermediate Similarity	NPC329636
0.6706	Remote Similarity	NPC484212
0.6667	Remote Similarity	NPC6108
0.6667	Remote Similarity	NPC89514
0.6207	Remote Similarity	NPC84949
0.6207	Remote Similarity	NPC480562
0.6207	Remote Similarity	NPC74945
0.6207	Remote Similarity	NPC10823
0.6207	Remote Similarity	NPC31354
0.6207	Remote Similarity	NPC69576
0.6105	Remote Similarity	NPC146857
0.6092	Remote Similarity	NPC17896
0.6092	Remote Similarity	NPC469755
0.6092	Remote Similarity	NPC284406
0.6092	Remote Similarity	NPC197707
0.6092	Remote Similarity	NPC251866
0.6067	Remote Similarity	NPC483822
0.587	Remote Similarity	NPC103534
0.587	Remote Similarity	NPC44899
0.587	Remote Similarity	NPC304260
0.587	Remote Similarity	NPC29639
0.5795	Remote Similarity	NPC219085
0.5686	Remote Similarity	NPC329675
0.5686	Remote Similarity	NPC194716
0.567	Remote Similarity	NPC469749
0.5652	Remote Similarity	NPC469753
0.5568	Remote Similarity	NPC474418
0.5556	Remote Similarity	NPC479356
0.5556	Remote Similarity	NPC479355
0.5543	Remote Similarity	NPC9499
0.5543	Remote Similarity	NPC471360
0.5543	Remote Similarity	NPC469751
0.5543	Remote Similarity	NPC471361
0.5543	Remote Similarity	NPC86159
0.5543	Remote Similarity	NPC469752
0.5543	Remote Similarity	NPC469754
0.5543	Remote Similarity	NPC70542
0.5521	Remote Similarity	NPC608063
0.5455	Remote Similarity	NPC247190
0.5376	Remote Similarity	NPC471359
0.5361	Remote Similarity	NPC32793
0.5361	Remote Similarity	NPC116075
0.5326	Remote Similarity	NPC152615
0.5181	Remote Similarity	NPC72772
0.5165	Remote Similarity	NPC99728
0.5165	Remote Similarity	NPC87250
0.5165	Remote Similarity	NPC244402
0.5165	Remote Similarity	NPC50305
0.5161	Remote Similarity	NPC24839
0.5158	Remote Similarity	NPC193893
0.5109	Remote Similarity	NPC484211
0.5054	Remote Similarity	NPC157376
0.5054	Remote Similarity	NPC142066
0.5054	Remote Similarity	NPC603972
0.5053	Remote Similarity	NPC484202

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC565896 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6229
0.1-0.2	2805
0.2-0.3	102
0.3-0.4	4
0.4-0.5	7
0.5-0.6	2
0.6-0.7	1
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
0.6092	Remote Similarity	NPD7319	Approved
0.5889	Remote Similarity	NPD7516	Pre-clinical
0.51	Remote Similarity	NPD8377	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