NPASS Compound

Natural Product: NPC283339

Natural Product ID	NPC283339
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QDGFOBJUAOZNRW-GAOADIEWSA-N
IUPAC Name	n.a.
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 79 84 0 0 0 0 0 0 0 0999 V2000 -0.3250 2.4347 -0.2779 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1913 0.9045 -0.1603 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7463 0.3476 -1.4328 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9817 -0.4571 -1.3001 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0115 0.0540 -0.3626 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4656 0.8406 0.7967 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0092 0.5496 1.0621 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8767 -0.8593 1.5108 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3961 -1.5239 1.0581 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4786 -0.4966 1.0687 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2460 0.5192 -0.0292 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1718 1.6642 0.2353 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3160 1.3258 1.1290 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9174 -0.0377 0.9191 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9340 -0.2625 2.0151 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6165 -0.1833 -0.3981 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4016 -1.6315 -0.8010 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0486 -1.9871 -0.1964 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8545 -1.1045 0.9861 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0275 -1.8491 2.1503 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0684 0.0843 -0.3690 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0505 -0.7753 -0.6440 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3376 -0.1080 -0.4970 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4835 -0.6160 -0.6775 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0705 1.1807 -0.1243 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6972 1.4082 -0.0220 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7030 2.2207 -0.9384 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0015 0.7495 -1.0544 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2489 0.1460 -0.9868 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2912 1.0106 -0.3574 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6226 0.3011 -0.4698 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4402 -1.1580 -0.8294 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5547 -1.3481 -2.0219 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7129 -0.2507 -2.2382 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6497 -1.7811 -1.0516 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2636 0.3243 0.7887 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9973 1.2177 0.9837 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4096 2.8917 0.7275 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3036 2.6050 -0.7736 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4441 2.8661 -0.9162 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9415 1.1406 -2.2157 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0223 -0.3120 -1.9382 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4610 -0.5147 -2.3232 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6958 -1.5314 -1.0982 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5318 -0.8459 0.0784 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6213 1.9313 0.6556 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0103 0.5876 1.7448 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6893 1.2717 1.8599 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8302 -0.8450 2.6404 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7864 -1.4908 1.2981 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6788 -2.3060 1.8221 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3051 -2.0699 0.1069 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4234 0.0538 2.0308 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6082 0.0252 -0.9763 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5856 2.4751 0.7627 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0018 1.3615 2.2136 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1298 2.0728 1.0492 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0933 0.6807 2.6160 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9351 -0.5082 1.5883 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6571 -1.0707 2.7227 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1914 0.4448 -1.2065 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1454 -2.3258 -0.3927 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3618 -1.7659 -1.8983 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2725 -1.9038 -0.9739 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0730 -3.0564 0.1114 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0727 -2.8188 1.9789 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9946 -1.8142 -0.9383 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3393 2.1456 -0.7673 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4832 1.7394 0.9908 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0995 3.0954 -0.6514 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1433 -0.7737 -0.3757 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3795 1.9591 -0.9272 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2780 0.7806 -1.2243 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9621 -1.6535 0.0484 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9845 -2.2897 -1.8799 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2121 -1.5396 -2.9139 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5837 -2.7543 -0.9973 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8945 1.0719 1.3309 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6291 2.1363 1.1000 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 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 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 1 16 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 12 27 1 0 5 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 7 2 1 0 19 10 1 0 26 21 1 0 34 29 1 0 11 2 1 0 19 14 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 5 45 1 1 6 46 1 0 6 47 1 0 7 48 1 1 8 49 1 0 8 50 1 0 9 51 1 0 9 52 1 0 10 53 1 1 11 54 1 6 12 55 1 1 13 56 1 0 13 57 1 0 15 58 1 0 15 59 1 0 15 60 1 0 16 61 1 6 17 62 1 0 17 63 1 0 18 64 1 0 18 65 1 0 20 66 1 0 22 67 1 0 26 68 1 0 26 69 1 0 27 70 1 0 29 71 1 1 30 72 1 6 31 73 1 6 32 74 1 1 33 75 1 0 33 76 1 0 35 77 1 0 36 78 1 0 37 79 1 0 M END

Standard InCHIKey	QDGFOBJUAOZNRW-GAOADIEWSA-N
Standard InCHI	InChI=1S/C28H42O9/c1-26-7-5-16(37-25-24(33)23(32)20(30)13-36-25)10-15(26)3-4-18-22(26)19(29)11-27(2)17(6-8-28(18,27)34)14-9-21(31)35-12-14/h9,15-20,22-25,29-30,32-34H,3-8,10-13H2,1-2H3/t15-,16+,17-,18-,19-,20+,22-,23-,24-,25+,26+,27-,28+/m1/s1
SMILES	C[C@]12CC[C@@H](C[C@H]1CC[C@@H]1[C@@H]2[C@@H](C[C@]2(C)[C@H](CC[C@]12O)C1=CC(=O)OC1)O)O[C@H]1[C@@H]([C@@H]([C@H](CO1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	522.28	Volume:	515.344 ? Van der Waals volume.
Dense:	1.013	LogP:	0.862 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.382 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.951 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	32.0
TPSA:	145.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.271	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.198	Fsp³:	0.893
MCE-18:	111.849 ? 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:	0.712	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.031 ? 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:	0.112	Promiscuous compounds:	0.348

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.389	MDCK Permeability:	-5.342
Pgp-inhibitor:	0.0	Pgp-substrate:	0.972
PAMPA:	0.984 ? 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):	0.026
20% Bioavailability (F20%):	0.781	30% Bioavailability (F30%):	0.345
50% Bioavailability (F50%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068	MRP1:	0.926
Plasma Protein Binding (PPB):	64.357%	Volume Distribution (VD):	-0.537
Fu:	33.526% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.963
OATP1B3 inhibitor:	0.935	BCRP inhibitor:	0.033
BSEP inhibitor:	0.071

ADMET: Metabolism

CYP1A2-inhibitor:	0.007	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:	0.001
CYP3A4-inhibitor:	0.072	CYP3A4-substrate:	0.008
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.079
HLM stability:	0.018 ? 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):

1.777

Half-life (T1/2):

2.466

ADMET: Toxicity

hERG Blockers:	0.18	hERG Blockers (10um):	0.579
Human Hepatotoxicity (H-HT):	0.741	Drug-induced Liver Injury (DILI):	0.343
AMES Toxicity:	0.88	Rat Oral Acute Toxicity:	0.966
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.734	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.984
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.887
Hematotoxicity:	0.726	Drug-induced Nephrotoxicity:	0.95
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.85
A549 Cytotoxicity:	0.932	Hek293 Cytotoxicity:	0.981
BCF:	0.7 ? 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:	4.671 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.029 ? 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
NPO8732	Thermopsis fabacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8732	Thermopsis fabacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8732	Thermopsis fabacea	Species	Fabaceae	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

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 NPC283339 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	13720
0.1-0.2	30530
0.2-0.3	5018
0.3-0.4	373
0.4-0.5	111
0.5-0.6	81
0.6-0.7	18
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	Natural Product ID
0.6962	Remote Similarity	NPC99620
0.679	Remote Similarity	NPC5311
0.6625	Remote Similarity	NPC158344
0.6463	Remote Similarity	NPC219085
0.6437	Remote Similarity	NPC30483
0.6437	Remote Similarity	NPC470897
0.6386	Remote Similarity	NPC469750
0.6351	Remote Similarity	NPC160583
0.631	Remote Similarity	NPC76572
0.631	Remote Similarity	NPC193382
0.619	Remote Similarity	NPC77299
0.619	Remote Similarity	NPC480906
0.618	Remote Similarity	NPC236973
0.6118	Remote Similarity	NPC199428
0.6118	Remote Similarity	NPC109448
0.6118	Remote Similarity	NPC310341
0.6118	Remote Similarity	NPC480914
0.6	Remote Similarity	NPC292467
0.5978	Remote Similarity	NPC486143
0.5978	Remote Similarity	NPC486142
0.5978	Remote Similarity	NPC486149
0.5952	Remote Similarity	NPC471633
0.5882	Remote Similarity	NPC196429
0.5843	Remote Similarity	NPC480907
0.5773	Remote Similarity	NPC486144
0.5773	Remote Similarity	NPC486145
0.5773	Remote Similarity	NPC486147
0.5773	Remote Similarity	NPC486148
0.5761	Remote Similarity	NPC240070
0.5747	Remote Similarity	NPC84949
0.5747	Remote Similarity	NPC480562
0.5747	Remote Similarity	NPC74945
0.5747	Remote Similarity	NPC31354
0.5747	Remote Similarity	NPC69576
0.5699	Remote Similarity	NPC264336
0.5684	Remote Similarity	NPC486146
0.5682	Remote Similarity	NPC83287
0.5667	Remote Similarity	NPC72260
0.5652	Remote Similarity	NPC32177
0.5652	Remote Similarity	NPC469756
0.5652	Remote Similarity	NPC275901
0.5632	Remote Similarity	NPC157376
0.5632	Remote Similarity	NPC142066
0.5632	Remote Similarity	NPC603972
0.5618	Remote Similarity	NPC179412
0.5618	Remote Similarity	NPC484202
0.5618	Remote Similarity	NPC93883
0.5618	Remote Similarity	NPC471356
0.5618	Remote Similarity	NPC471353
0.5612	Remote Similarity	NPC475590
0.56	Remote Similarity	NPC474908
0.5591	Remote Similarity	NPC188234
0.5591	Remote Similarity	NPC480910
0.5591	Remote Similarity	NPC480909
0.5591	Remote Similarity	NPC608063
0.5581	Remote Similarity	NPC99728
0.5581	Remote Similarity	NPC87250
0.5581	Remote Similarity	NPC244402
0.5581	Remote Similarity	NPC50305
0.5568	Remote Similarity	NPC604978
0.5506	Remote Similarity	NPC250556
0.55	Remote Similarity	NPC74259
0.55	Remote Similarity	NPC475419
0.5474	Remote Similarity	NPC59288
0.5474	Remote Similarity	NPC486135
0.5474	Remote Similarity	NPC486137
0.5455	Remote Similarity	NPC48463
0.5455	Remote Similarity	NPC17896
0.5455	Remote Similarity	NPC469755
0.5455	Remote Similarity	NPC284406
0.5455	Remote Similarity	NPC197707
0.5455	Remote Similarity	NPC251866
0.5455	Remote Similarity	NPC480915
0.5446	Remote Similarity	NPC486134
0.5446	Remote Similarity	NPC486141
0.5444	Remote Similarity	NPC305574
0.5417	Remote Similarity	NPC232785
0.5417	Remote Similarity	NPC486139
0.5347	Remote Similarity	NPC120390
0.5341	Remote Similarity	NPC84987
0.5312	Remote Similarity	NPC125077
0.5312	Remote Similarity	NPC55532
0.5312	Remote Similarity	NPC208193
0.53	Remote Similarity	NPC486136
0.5288	Remote Similarity	NPC474423
0.5204	Remote Similarity	NPC329986
0.5204	Remote Similarity	NPC140092
0.5189	Remote Similarity	NPC286809
0.5169	Remote Similarity	NPC309034
0.5158	Remote Similarity	NPC27363
0.5158	Remote Similarity	NPC40749
0.5152	Remote Similarity	NPC486138
0.5152	Remote Similarity	NPC276838
0.5111	Remote Similarity	NPC479356
0.5111	Remote Similarity	NPC479355
0.5109	Remote Similarity	NPC483822
0.5106	Remote Similarity	NPC173555
0.5052	Remote Similarity	NPC231518
0.5052	Remote Similarity	NPC488944

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC283339 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5754
0.1-0.2	3257
0.2-0.3	121
0.3-0.4	5
0.4-0.5	3
0.5-0.6	10
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
0.5682	Remote Similarity	NPD7327	Approved
0.5682	Remote Similarity	NPD7328	Phase 4
0.5667	Remote Similarity	NPD8294	Phase 4
0.5506	Remote Similarity	NPD7507	Pre-clinical
0.5455	Remote Similarity	NPD7319	Approved
0.5333	Remote Similarity	NPD8335	Phase 4
0.5312	Remote Similarity	NPD8377	Phase 4
0.5275	Remote Similarity	NPD8380	Approved
0.5106	Remote Similarity	NPD8296	Phase 4
0.5052	Remote Similarity	NPD8033	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