NPASS Compound

Natural Product: NPC529883

Natural Product ID	NPC529883
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cymarol
IUPAC Name	3-[(3~{S},5~{S},8~{R},9~{S},10~{R},13~{R},14~{S},17~{R})-5,14-dihydroxy-3-[(2~{R},4~{S},5~{R},6~{R})-5-hydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-10-(hydroxymethyl)-13-methyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1~{H}-cyclopenta[a]phenanthren-17-yl]-2~{H}-furan-5-one
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 85 90 0 0 0 0 0 0 0 0999 V2000 7.8361 -2.6379 -1.5766 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2228 -2.1575 -0.4237 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2416 -1.2059 -0.7190 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9596 -1.6194 -0.1075 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3896 -0.7012 0.9157 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6495 0.3086 0.3086 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3196 0.2337 0.6682 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8716 1.4658 1.4196 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3916 1.4447 1.6084 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4044 1.5376 0.3304 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8816 2.9575 0.1938 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6826 3.3900 1.2393 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5158 0.5163 0.4111 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3370 0.5476 1.6360 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7713 0.8269 1.5029 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4836 0.2539 0.2763 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1742 1.4677 -0.3657 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3517 -0.8124 0.7279 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5696 -1.2175 0.0346 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1448 -0.8206 -1.0635 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3675 -1.5855 -1.2911 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1215 -1.4063 -2.2835 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4711 -2.4628 -0.2465 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4176 -2.2900 0.6210 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4605 -2.0362 0.7869 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3076 -1.7174 -0.1213 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5352 -0.3675 -0.6887 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0910 -0.4497 -1.9772 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3123 0.4873 -0.8590 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3844 -0.0760 -1.9328 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2519 0.8806 -2.0856 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5060 1.1484 -0.8170 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3275 2.2662 -1.0812 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4085 -0.0064 -0.5106 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2819 -0.1137 1.7693 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5979 -0.2025 1.4336 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4465 0.7954 2.1489 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7062 0.0918 -0.0684 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0397 0.3522 -0.4049 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5923 -3.3798 -1.2468 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4162 -1.8320 -2.1014 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1341 -3.1514 -2.2510 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1949 -1.0667 -1.8210 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1978 -1.6889 -0.9413 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0283 -2.6544 0.2874 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6771 -1.2897 1.5301 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1496 -0.6270 1.3687 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3094 1.3520 2.4560 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2873 2.4010 1.0388 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1381 2.2865 2.3102 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1420 0.5201 2.1842 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4552 3.1283 -0.7400 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0211 3.6022 0.1968 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2561 4.0810 1.8031 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9470 -0.4683 0.4137 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8964 1.3441 2.3095 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1840 -0.3764 2.2762 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2718 0.4281 2.4408 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9470 1.9291 1.6117 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2202 1.5775 -0.0351 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9965 1.5328 -1.4462 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7003 2.4317 0.0131 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6877 -0.5729 1.7946 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7387 -0.0321 -1.6863 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8093 -1.9276 1.6058 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8537 -3.2150 0.8537 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1483 -2.2729 1.8219 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9238 -2.9526 0.3950 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2521 -2.4292 -0.9999 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3907 -1.8879 0.4327 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8181 0.3011 -2.5613 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6401 1.4763 -1.2213 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0487 -1.0683 -1.5347 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8734 -0.2069 -2.8985 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6468 1.8377 -2.4545 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4655 0.4682 -2.8184 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5133 2.3600 -2.0447 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0360 -0.1557 -1.4379 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8337 -0.9550 -0.4286 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9286 -1.2616 1.6021 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4619 0.3295 2.3115 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6521 1.7127 1.5383 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0635 1.0600 3.1492 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0434 0.9171 -0.3365 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2608 1.3093 -0.3731 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 6 11 12 1 0 10 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 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 26 27 1 0 27 28 1 6 27 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 6 32 34 1 0 5 35 1 0 35 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 38 3 1 0 34 7 1 0 32 10 1 0 29 13 1 0 27 16 1 0 24 19 1 0 1 40 1 0 1 41 1 0 1 42 1 0 3 43 1 6 4 44 1 0 4 45 1 0 5 46 1 1 7 47 1 1 8 48 1 0 8 49 1 0 9 50 1 0 9 51 1 0 11 52 1 0 11 53 1 0 12 54 1 0 13 55 1 1 14 56 1 0 14 57 1 0 15 58 1 0 15 59 1 0 17 60 1 0 17 61 1 0 17 62 1 0 18 63 1 1 20 64 1 0 24 65 1 0 24 66 1 0 25 67 1 0 25 68 1 0 26 69 1 0 26 70 1 0 28 71 1 0 29 72 1 6 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 33 77 1 0 34 78 1 0 34 79 1 0 36 80 1 6 37 81 1 0 37 82 1 0 37 83 1 0 38 84 1 6 39 85 1 0 M END

Standard InCHIKey	WPKQVDYSPWCVGM-ZNDDOCHDSA-N
Standard InCHI	InChI=1S/C30H46O9/c1-17-26(33)23(36-3)13-25(38-17)39-19-4-9-28(16-31)21-5-8-27(2)20(18-12-24(32)37-15-18)7-11-30(27,35)22(21)6-10-29(28,34)14-19/h12,17,19-23,25-26,31,33-35H,4-11,13-16H2,1-3H3/t17-,19+,20-,21+,22-,23+,25+,26-,27-,28+,29+,30+/m1/s1
SMILES	CO[C@H]1C[C@H](O[C@H]2CC[C@]3(CO)[C@H]4CC[C@]5(C)[C@@H](C6=CC(=O)OC6)CC[C@]5(O)[C@@H]4CC[C@]3(O)C2)O[C@H](C)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	550.31	Volume:	549.936 ? Van der Waals volume.
Dense:	1.001	LogP:	0.967 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.542 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.054 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	32.0
TPSA:	134.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.3	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.343	Fsp³:	0.9
MCE-18:	112.281 ? 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:	0.732	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? 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:	0.167	Promiscuous compounds:	0.632

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.741	MDCK Permeability:	-5.157
Pgp-inhibitor:	0.0	Pgp-substrate:	0.999
PAMPA:	0.998 ? 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):	0.05
20% Bioavailability (F20%):	0.718	30% Bioavailability (F30%):	0.503
50% Bioavailability (F50%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.086	MRP1:	0.897
Plasma Protein Binding (PPB):	58.841%	Volume Distribution (VD):	-0.147
Fu:	45.623% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.697
OATP1B3 inhibitor:	0.576	BCRP inhibitor:	0.061
BSEP inhibitor:	0.091

ADMET: Metabolism

CYP1A2-inhibitor:	0.897	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.083	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.069
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.053
HLM stability:	0.023 ? 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):

4.372

Half-life (T1/2):

3.212

ADMET: Toxicity

hERG Blockers:	0.283	hERG Blockers (10um):	0.784
Human Hepatotoxicity (H-HT):	0.779	Drug-induced Liver Injury (DILI):	0.756
AMES Toxicity:	0.85	Rat Oral Acute Toxicity:	0.991
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.962	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.996
Drug-induced Neurotoxicity:	0.021	Ototoxicity:	0.71
Hematotoxicity:	0.455	Drug-induced Nephrotoxicity:	0.963
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.852
A549 Cytotoxicity:	0.932	Hek293 Cytotoxicity:	0.993
BCF:	0.58 ? 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:	3.237 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.684 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.939 ? 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]
NPO43232	Adonis aestivalis L.	Genus	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO49701	Adonis annua L.	Genus	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO63942	Adonis flammea Jacq.	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 NPC529883 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	13968
0.1-0.2	31583
0.2-0.3	3997
0.3-0.4	107
0.4-0.5	96
0.5-0.6	68
0.6-0.7	23
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8667	High Similarity	NPC34390
0.8442	Intermediate Similarity	NPC180079
0.7654	Intermediate Similarity	NPC483822
0.7407	Intermediate Similarity	NPC84949
0.7407	Intermediate Similarity	NPC480562
0.7407	Intermediate Similarity	NPC74945
0.7407	Intermediate Similarity	NPC31354
0.7407	Intermediate Similarity	NPC69576
0.7284	Intermediate Similarity	NPC157376
0.7284	Intermediate Similarity	NPC142066
0.7284	Intermediate Similarity	NPC603972
0.7065	Intermediate Similarity	NPC329636
0.6905	Remote Similarity	NPC484212
0.6707	Remote Similarity	NPC474418
0.6667	Remote Similarity	NPC6108
0.6667	Remote Similarity	NPC89514
0.6277	Remote Similarity	NPC146857
0.6235	Remote Similarity	NPC99728
0.6235	Remote Similarity	NPC87250
0.6235	Remote Similarity	NPC244402
0.6235	Remote Similarity	NPC50305
0.6207	Remote Similarity	NPC10823
0.618	Remote Similarity	NPC471354
0.618	Remote Similarity	NPC27507
0.6163	Remote Similarity	NPC84987
0.6118	Remote Similarity	NPC158344
0.6092	Remote Similarity	NPC17896
0.6092	Remote Similarity	NPC469755
0.6092	Remote Similarity	NPC284406
0.6092	Remote Similarity	NPC99080
0.6092	Remote Similarity	NPC197707
0.6092	Remote Similarity	NPC251866
0.6067	Remote Similarity	NPC484202
0.6026	Remote Similarity	NPC10232
0.6023	Remote Similarity	NPC152615
0.5977	Remote Similarity	NPC219085
0.5957	Remote Similarity	NPC475629
0.5889	Remote Similarity	NPC305574
0.587	Remote Similarity	NPC103534
0.587	Remote Similarity	NPC44899
0.587	Remote Similarity	NPC304260
0.587	Remote Similarity	NPC29639
0.5851	Remote Similarity	NPC475556
0.5851	Remote Similarity	NPC311706
0.5842	Remote Similarity	NPC329675
0.5842	Remote Similarity	NPC194716
0.5833	Remote Similarity	NPC469749
0.5714	Remote Similarity	NPC93883
0.5684	Remote Similarity	NPC608063
0.5682	Remote Similarity	NPC471633
0.5667	Remote Similarity	NPC199428
0.5667	Remote Similarity	NPC109448
0.5667	Remote Similarity	NPC310341
0.5612	Remote Similarity	NPC247190
0.5604	Remote Similarity	NPC250556
0.5556	Remote Similarity	NPC477580
0.5521	Remote Similarity	NPC32793
0.5521	Remote Similarity	NPC116075
0.5495	Remote Similarity	NPC76572
0.5495	Remote Similarity	NPC193382
0.5464	Remote Similarity	NPC264336
0.5455	Remote Similarity	NPC329986
0.5455	Remote Similarity	NPC140092
0.5435	Remote Similarity	NPC77319
0.5435	Remote Similarity	NPC471351
0.5435	Remote Similarity	NPC471355
0.5408	Remote Similarity	NPC55532
0.5385	Remote Similarity	NPC77299
0.5385	Remote Similarity	NPC480906
0.5375	Remote Similarity	NPC97487
0.5366	Remote Similarity	NPC72772
0.5333	Remote Similarity	NPC99620
0.5319	Remote Similarity	NPC469753
0.5275	Remote Similarity	NPC484211
0.5275	Remote Similarity	NPC486129
0.5263	Remote Similarity	NPC72260
0.5253	Remote Similarity	NPC486135
0.5253	Remote Similarity	NPC486137
0.5217	Remote Similarity	NPC486126
0.5217	Remote Similarity	NPC5311
0.5217	Remote Similarity	NPC469750
0.5213	Remote Similarity	NPC9499
0.5213	Remote Similarity	NPC471360
0.5213	Remote Similarity	NPC469751
0.5213	Remote Similarity	NPC471361
0.5213	Remote Similarity	NPC86159
0.5213	Remote Similarity	NPC469752
0.5213	Remote Similarity	NPC469754
0.5213	Remote Similarity	NPC70542
0.5204	Remote Similarity	NPC603096
0.5165	Remote Similarity	NPC473852
0.5161	Remote Similarity	NPC480914
0.5143	Remote Similarity	NPC475419
0.5109	Remote Similarity	NPC309034
0.5106	Remote Similarity	NPC290693
0.51	Remote Similarity	NPC486143
0.51	Remote Similarity	NPC486142
0.51	Remote Similarity	NPC486149
0.5053	Remote Similarity	NPC471359
0.5051	Remote Similarity	NPC480910
0.5051	Remote Similarity	NPC480909
0.505	Remote Similarity	NPC232785
0.505	Remote Similarity	NPC486139

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC529883 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5797
0.1-0.2	3218
0.2-0.3	121
0.3-0.4	0
0.4-0.5	7
0.5-0.6	4
0.6-0.7	2
0.7-0.8	1
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
0.7024	Intermediate Similarity	NPD7516	Pre-clinical
0.6092	Remote Similarity	NPD7319	Approved
0.6064	Remote Similarity	NPD8377	Phase 4
0.5604	Remote Similarity	NPD7507	Pre-clinical
0.5263	Remote Similarity	NPD8294	Phase 4
0.52	Remote Similarity	NPD8378	Pre-clinical
0.52	Remote Similarity	NPD8379	Approved

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