NPASS Compound

Natural Product: NPC550636

Natural Product ID	NPC550636
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3~{S},5~{S},8~{R},9~{S},10~{S},12~{R},13~{S},14~{S},17~{R})-3-[(2~{R},3~{R},4~{R},5~{S},6~{R})-4,5-dihydroxy-3-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-5,12,14-trihydroxy-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
IUPAC Name	(3~{S},5~{S},8~{R},9~{S},10~{S},12~{R},13~{S},14~{S},17~{R})-3-[(2~{R},3~{R},4~{R},5~{S},6~{R})-4,5-dihydroxy-3-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-5,12,14-trihydroxy-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] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides 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 85 90 0 0 0 0 0 0 0 0999 V2000 -5.7934 1.5845 -3.1295 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0324 1.5188 -1.7610 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3539 0.4801 -1.1526 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3514 0.9569 -0.1304 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6153 -0.1575 0.2695 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2582 -0.0417 -0.0311 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4790 -0.1081 1.2599 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6935 -1.3623 1.4120 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2387 -1.6485 0.2336 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3929 -3.1557 0.2498 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1280 -3.8819 1.0436 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5981 -1.0966 0.5479 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6122 -2.1892 0.8775 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8314 -1.5238 1.4534 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7891 -2.5283 1.6435 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4584 -0.4869 0.5158 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2094 -1.2669 -0.5305 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2766 0.4296 1.3531 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2471 1.2720 0.6007 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1500 2.5953 0.4789 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2610 3.1057 -0.3118 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4503 4.3411 -0.6099 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0172 2.0275 -0.6472 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4658 0.8638 -0.1139 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1977 1.2881 1.9980 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1529 1.5015 0.9315 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4370 0.4220 -0.0784 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0227 1.0434 -1.1963 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2162 -0.2876 -0.5534 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1823 0.7056 -1.0292 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1170 -0.0610 -1.7435 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3409 -1.2948 -1.0764 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1738 -2.3581 -1.9987 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8641 -1.2050 -0.9061 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9416 1.6094 0.9358 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2583 1.2897 1.1411 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6022 1.7086 2.5767 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5095 -0.1826 0.9650 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8795 -0.4087 1.2092 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2551 -0.5152 -0.4903 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4448 -0.7014 -1.1845 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0869 0.6898 -3.6777 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3818 2.4455 -3.5182 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7134 1.8708 -3.2940 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7748 -0.0502 -1.9407 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6458 1.6726 -0.5998 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1373 0.9444 -0.5247 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8848 0.8240 1.3695 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1840 -0.0849 2.1433 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4229 -2.2000 1.5568 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1080 -1.2989 2.3419 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0342 -3.5757 -0.5359 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5447 -0.4860 1.4724 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2133 -2.8404 1.6947 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8223 -2.7415 -0.0347 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5836 -1.1033 2.4246 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5365 -3.0686 2.4482 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1740 -1.5837 -0.0872 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5942 -2.2086 -0.7229 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2536 -0.7896 -1.5087 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8314 -0.1241 2.1463 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3815 3.2524 0.8831 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1822 0.3240 0.5596 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2614 0.2174 -1.0253 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7717 0.8008 2.9054 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6477 2.2163 2.3520 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1483 1.4366 1.3961 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1836 2.5031 0.4599 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7498 0.5979 -2.0238 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -0.9464 -1.3839 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8183 1.3657 -0.2240 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6899 1.3773 -1.7612 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5245 -0.2570 -2.7821 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7166 0.6744 -1.9521 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6309 -2.1551 -2.8478 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1883 -2.1266 -0.3752 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3347 -1.1889 -1.8883 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9630 1.8345 0.4922 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7272 2.8094 2.6286 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5747 1.2457 2.8198 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7865 1.4001 3.2710 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8713 -0.7428 1.6591 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3469 -0.0815 0.3997 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7207 -1.4965 -0.4924 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5705 -1.6341 -1.4705 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 6 10 11 2 0 9 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 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 4 35 1 0 35 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 38 40 1 0 40 41 1 0 40 3 1 0 34 6 1 0 32 9 1 0 29 12 1 0 27 16 1 0 24 19 1 0 1 42 1 0 1 43 1 0 1 44 1 0 3 45 1 6 4 46 1 6 6 47 1 6 7 48 1 0 7 49 1 0 8 50 1 0 8 51 1 0 10 52 1 0 12 53 1 1 13 54 1 0 13 55 1 0 14 56 1 1 15 57 1 0 17 58 1 0 17 59 1 0 17 60 1 0 18 61 1 1 20 62 1 0 24 63 1 0 24 64 1 0 25 65 1 0 25 66 1 0 26 67 1 0 26 68 1 0 28 69 1 0 29 70 1 6 30 71 1 0 30 72 1 0 31 73 1 0 31 74 1 0 33 75 1 0 34 76 1 0 34 77 1 0 36 78 1 6 37 79 1 0 37 80 1 0 37 81 1 0 38 82 1 1 39 83 1 0 40 84 1 1 41 85 1 0 M END

Standard InCHIKey	WUAYGHQTMPWDRU-LBJUOORFSA-N
Standard InCHI	InChI=1S/C30H44O11/c1-15-23(34)24(35)25(38-3)26(40-15)41-17-4-7-28(14-31)20-11-21(32)27(2)18(16-10-22(33)39-13-16)6-9-30(27,37)19(20)5-8-29(28,36)12-17/h10,14-15,17-21,23-26,32,34-37H,4-9,11-13H2,1-3H3/t15-,17+,18-,19-,20+,21-,23-,24-,25-,26+,27+,28+,29+,30+/m1/s1
SMILES	CO[C@H]1[C@H](O[C@H]2CC[C@]3(C=O)[C@H]4C[C@@H](O)[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](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	580.29	Volume:	564.88 ? Van der Waals volume.
Dense:	1.027	LogP:	0.232 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.005 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.845 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	33.0
TPSA:	172.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.173	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.562	Fsp³:	0.867
MCE-18:	118.5 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.637	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? 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:	0.154	Promiscuous compounds:	0.62

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.643	MDCK Permeability:	-5.134
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
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):	0.141
20% Bioavailability (F20%):	0.536	30% Bioavailability (F30%):	0.473
50% Bioavailability (F50%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.59
Plasma Protein Binding (PPB):	28.857%	Volume Distribution (VD):	-0.631
Fu:	79.813% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.901
OATP1B3 inhibitor:	0.947	BCRP inhibitor:	0.013
BSEP inhibitor:	0.194

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.37	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.007 ? 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):

1.793

Half-life (T1/2):

4.926

ADMET: Toxicity

hERG Blockers:	0.218	hERG Blockers (10um):	0.718
Human Hepatotoxicity (H-HT):	0.573	Drug-induced Liver Injury (DILI):	0.102
AMES Toxicity:	0.709	Rat Oral Acute Toxicity:	0.995
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.894	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.998
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.825
Hematotoxicity:	0.43	Drug-induced Nephrotoxicity:	0.966
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.923
A549 Cytotoxicity:	0.608	Hek293 Cytotoxicity:	0.985
BCF:	0.491 ? 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:	3.167 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.668 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.816 ? 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
NPO62227	Antiaris toxicaria LESCH.	Genus	Moraceae	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 NPC550636 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	15776
0.1-0.2	29921
0.2-0.3	3888
0.3-0.4	133
0.4-0.5	85
0.5-0.6	27
0.6-0.7	14
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469753
0.8101	Intermediate Similarity	NPC10823
0.7683	Intermediate Similarity	NPC9499
0.7683	Intermediate Similarity	NPC471360
0.7683	Intermediate Similarity	NPC469751
0.7683	Intermediate Similarity	NPC471361
0.7683	Intermediate Similarity	NPC86159
0.7683	Intermediate Similarity	NPC469752
0.7683	Intermediate Similarity	NPC469754
0.7683	Intermediate Similarity	NPC70542
0.7059	Intermediate Similarity	NPC471359
0.6706	Remote Similarity	NPC6108
0.6706	Remote Similarity	NPC89514
0.6552	Remote Similarity	NPC77319
0.6552	Remote Similarity	NPC471351
0.6552	Remote Similarity	NPC471355
0.6404	Remote Similarity	NPC471354
0.6404	Remote Similarity	NPC27507
0.6329	Remote Similarity	NPC469794
0.618	Remote Similarity	NPC180079
0.6136	Remote Similarity	NPC17896
0.6136	Remote Similarity	NPC469755
0.6136	Remote Similarity	NPC284406
0.6136	Remote Similarity	NPC197707
0.6136	Remote Similarity	NPC251866
0.5934	Remote Similarity	NPC179412
0.5934	Remote Similarity	NPC471356
0.5667	Remote Similarity	NPC219085
0.5657	Remote Similarity	NPC247190
0.5618	Remote Similarity	NPC474418
0.5591	Remote Similarity	NPC471353
0.55	Remote Similarity	NPC146857
0.5435	Remote Similarity	NPC34390
0.5417	Remote Similarity	NPC173555
0.5385	Remote Similarity	NPC99728
0.5385	Remote Similarity	NPC87250
0.5385	Remote Similarity	NPC244402
0.5385	Remote Similarity	NPC50305
0.5288	Remote Similarity	NPC329636
0.5269	Remote Similarity	NPC157376
0.5269	Remote Similarity	NPC142066
0.5269	Remote Similarity	NPC603972
0.5253	Remote Similarity	NPC32793
0.5253	Remote Similarity	NPC116075
0.5253	Remote Similarity	NPC608063
0.5248	Remote Similarity	NPC469749
0.5172	Remote Similarity	NPC475030
0.5161	Remote Similarity	NPC484211
0.514	Remote Similarity	NPC329675
0.514	Remote Similarity	NPC194716
0.5119	Remote Similarity	NPC189588
0.5104	Remote Similarity	NPC93883

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC550636 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6312
0.1-0.2	2765
0.2-0.3	59
0.3-0.4	3
0.4-0.5	7
0.5-0.6	3
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
0.6136	Remote Similarity	NPD7319	Approved
0.5484	Remote Similarity	NPD8335	Phase 4
0.5417	Remote Similarity	NPD8296	Phase 4
0.5104	Remote Similarity	NPD8380	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