NPASS Compound

Natural Product: NPC579794

Natural Product ID	NPC579794
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-[(3~{S},5~{R},10~{S},13~{R},14~{S},17~{R})-14-hydroxy-10,13-dimethyl-3-[(2~{S},5~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2~{H}-furan-5-one
IUPAC Name	3-[(3~{S},5~{R},10~{S},13~{R},14~{S},17~{R})-14-hydroxy-10,13-dimethyl-3-[(2~{S},5~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[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 81 86 0 0 0 0 0 0 0 0999 V2000 7.7718 1.1333 1.4643 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0315 0.3923 0.3544 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6798 0.6285 0.5575 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8865 0.2014 -0.4771 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9978 -0.7531 0.0507 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6740 -0.3537 -0.0946 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0100 -1.3669 -1.0253 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5487 -0.9025 -1.1069 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0828 -1.2234 0.2307 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3417 -2.6617 0.5605 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5616 -1.0625 0.1867 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0845 -0.6448 -1.1455 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3583 0.1049 -1.1423 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2923 -0.1838 0.0100 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9351 -1.5196 -0.1878 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2085 0.9760 0.1353 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4168 1.0331 -0.6424 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9635 0.2671 -1.5578 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2388 0.8075 -2.0354 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9954 0.3178 -2.8959 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4364 1.9690 -1.3415 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3716 2.1736 -0.4772 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5844 0.9707 1.6341 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1393 0.9507 2.1698 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5851 -0.2033 1.3510 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0139 -1.3499 2.0627 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1049 -0.1957 1.2956 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4676 1.1560 1.3206 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0253 1.0498 1.2771 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5526 -0.3483 1.2787 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0354 -0.3180 1.2420 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6130 -0.4418 -1.6095 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9713 -1.7427 -1.2444 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8255 0.2947 -2.0765 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8097 -0.5965 -2.5475 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4176 1.0746 -0.9408 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8072 1.1325 -1.0490 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4955 0.6034 2.4218 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3361 2.1419 1.5556 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8532 1.1339 1.3120 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2976 -0.6817 0.3608 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3188 1.0714 -0.8969 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6181 0.6395 -0.6006 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1061 -2.3922 -0.6768 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4819 -1.2190 -2.0237 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1089 -1.4307 -1.9482 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6345 0.2125 -1.2678 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4763 -3.0459 1.2386 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3162 -3.3028 -0.3244 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2583 -2.6973 1.1527 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9987 -2.0875 0.3895 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3375 -0.0131 -1.7135 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1692 -1.5680 -1.7922 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9242 -0.1870 -2.0723 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2457 1.2046 -1.2325 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7602 -1.9449 -1.2150 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4214 -2.2929 0.4709 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9910 -1.5859 0.1400 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6238 1.9456 0.0398 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5689 -0.6463 -1.9494 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6589 2.3270 0.5804 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8020 3.0776 -0.8419 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1218 1.8679 1.9247 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0327 0.0134 1.8894 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7166 1.9304 1.8530 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1049 0.7694 3.2421 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7690 -1.2106 3.0255 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7560 -0.7024 2.2488 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7532 1.6319 2.3064 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7843 1.8490 0.5452 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4940 1.5837 2.1348 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4478 1.5635 0.3641 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2718 -0.8081 2.2734 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3639 0.6378 1.7466 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4737 -1.1264 1.8633 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9009 -0.4807 -2.4774 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1587 -2.3362 -1.3283 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5962 1.0336 -2.8925 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1452 -0.2843 -3.4461 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0216 2.1186 -0.8793 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1587 1.9227 -0.5543 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 1 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 16 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 4 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 36 2 1 0 31 6 1 0 30 9 1 0 27 11 1 0 25 14 1 0 22 17 1 0 1 38 1 0 1 39 1 0 1 40 1 0 2 41 1 0 4 42 1 6 6 43 1 6 7 44 1 0 7 45 1 0 8 46 1 0 8 47 1 0 10 48 1 0 10 49 1 0 10 50 1 0 11 51 1 0 12 52 1 0 12 53 1 0 13 54 1 0 13 55 1 0 15 56 1 0 15 57 1 0 15 58 1 0 16 59 1 1 18 60 1 0 22 61 1 0 22 62 1 0 23 63 1 0 23 64 1 0 24 65 1 0 24 66 1 0 26 67 1 0 27 68 1 0 28 69 1 0 28 70 1 0 29 71 1 0 29 72 1 0 30 73 1 1 31 74 1 0 31 75 1 0 32 76 1 0 33 77 1 0 34 78 1 0 35 79 1 0 36 80 1 1 37 81 1 0 M END

Standard InCHIKey	WQMLFJWIKARBFW-IRVRIFDVSA-N
Standard InCHI	InChI=1S/C29H44O8/c1-15-23(31)24(32)25(33)26(36-15)37-18-6-9-27(2)17(13-18)4-5-21-20(27)7-10-28(3)19(8-11-29(21,28)34)16-12-22(30)35-14-16/h12,15,17-21,23-26,31-34H,4-11,13-14H2,1-3H3/t15?,17-,18+,19-,20?,21?,23-,24?,25?,26-,27+,28-,29+/m1/s1
SMILES	CC1O[C@H](O[C@H]2CC[C@]3(C)C4CC[C@]5(C)[C@@H](C6=CC(=O)OC6)CC[C@]5(O)C4CC[C@@H]3C2)C(O)C(O)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	520.3	Volume:	523.85 ? Van der Waals volume.
Dense:	0.993	LogP:	1.734 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.341 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.113 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	32.0
TPSA:	125.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.33	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.016	Fsp³:	0.897
MCE-18:	110.618 ? 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:	0.7	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.039 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.081	Promiscuous compounds:	0.038

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.255	MDCK Permeability:	-5.235
Pgp-inhibitor:	0.008	Pgp-substrate:	0.948
PAMPA:	0.992 ? 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):	0.002
20% Bioavailability (F20%):	0.591	30% Bioavailability (F30%):	0.369
50% Bioavailability (F50%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.219	MRP1:	0.963
Plasma Protein Binding (PPB):	83.81%	Volume Distribution (VD):	-0.389
Fu:	14.258% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.988
OATP1B3 inhibitor:	0.96	BCRP inhibitor:	0.055
BSEP inhibitor:	0.585

ADMET: Metabolism

CYP1A2-inhibitor:	0.264	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.979	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.015	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.994	CYP3A4-substrate:	0.927
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.705
HLM stability:	0.188 ? 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):

3.801

Half-life (T1/2):

2.456

ADMET: Toxicity

hERG Blockers:	0.392	hERG Blockers (10um):	0.887
Human Hepatotoxicity (H-HT):	0.832	Drug-induced Liver Injury (DILI):	0.732
AMES Toxicity:	0.744	Rat Oral Acute Toxicity:	0.981
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.865	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.988
Drug-induced Neurotoxicity:	0.015	Ototoxicity:	0.78
Hematotoxicity:	0.222	Drug-induced Nephrotoxicity:	0.548
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.703
A549 Cytotoxicity:	0.595	Hek293 Cytotoxicity:	0.989
BCF:	0.814 ? 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:	3.551 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.275 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.387 ? 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
NPO12405	Descurainia sophia	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12405	Descurainia sophia	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12405	Descurainia sophia	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12405	Descurainia sophia	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12405	Descurainia sophia	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12405	Descurainia sophia	Species	Brassicaceae	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 NPC579794 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	13422
0.1-0.2	29875
0.2-0.3	5712
0.3-0.4	604
0.4-0.5	56
0.5-0.6	70
0.6-0.7	66
0.7-0.8	2
0.8-0.85	5
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC99620
0.8889	High Similarity	NPC5311
0.863	High Similarity	NPC469750
0.8514	High Similarity	NPC76572
0.8514	High Similarity	NPC193382
0.8108	Intermediate Similarity	NPC471633
0.8101	Intermediate Similarity	NPC30483
0.8101	Intermediate Similarity	NPC470897
0.8	Intermediate Similarity	NPC236973
0.8	Intermediate Similarity	NPC196429
0.7792	Intermediate Similarity	NPC199428
0.7792	Intermediate Similarity	NPC109448
0.7792	Intermediate Similarity	NPC310341
0.7778	Intermediate Similarity	NPC292467
0.7711	Intermediate Similarity	NPC486143
0.7711	Intermediate Similarity	NPC486142
0.7711	Intermediate Similarity	NPC486149
0.7683	Intermediate Similarity	NPC240070
0.7662	Intermediate Similarity	NPC77299
0.7662	Intermediate Similarity	NPC480906
0.7632	Intermediate Similarity	NPC99728
0.7632	Intermediate Similarity	NPC87250
0.7632	Intermediate Similarity	NPC244402
0.7632	Intermediate Similarity	NPC50305
0.7625	Intermediate Similarity	NPC72260
0.7564	Intermediate Similarity	NPC480914
0.7436	Intermediate Similarity	NPC157376
0.7436	Intermediate Similarity	NPC17896
0.7436	Intermediate Similarity	NPC469755
0.7436	Intermediate Similarity	NPC284406
0.7436	Intermediate Similarity	NPC197707
0.7436	Intermediate Similarity	NPC251866
0.7436	Intermediate Similarity	NPC142066
0.7436	Intermediate Similarity	NPC480915
0.7436	Intermediate Similarity	NPC603972
0.7342	Intermediate Similarity	NPC84949
0.7342	Intermediate Similarity	NPC480562
0.7342	Intermediate Similarity	NPC74945
0.7342	Intermediate Similarity	NPC31354
0.7342	Intermediate Similarity	NPC69576
0.7326	Intermediate Similarity	NPC486146
0.7195	Intermediate Similarity	NPC480907
0.7191	Intermediate Similarity	NPC486144
0.7191	Intermediate Similarity	NPC486145
0.7191	Intermediate Similarity	NPC486147
0.7191	Intermediate Similarity	NPC486148
0.716	Intermediate Similarity	NPC179412
0.716	Intermediate Similarity	NPC471356
0.716	Intermediate Similarity	NPC471353
0.7	Intermediate Similarity	NPC475590
0.6951	Remote Similarity	NPC93883
0.6941	Remote Similarity	NPC32177
0.6941	Remote Similarity	NPC469756
0.6941	Remote Similarity	NPC275901
0.686	Remote Similarity	NPC188234
0.686	Remote Similarity	NPC480910
0.686	Remote Similarity	NPC480909
0.6848	Remote Similarity	NPC120390
0.6848	Remote Similarity	NPC74259
0.6848	Remote Similarity	NPC475419
0.6774	Remote Similarity	NPC474908
0.6774	Remote Similarity	NPC486134
0.6774	Remote Similarity	NPC486141
0.6747	Remote Similarity	NPC484202
0.6705	Remote Similarity	NPC55532
0.6705	Remote Similarity	NPC486135
0.6705	Remote Similarity	NPC486137
0.6667	Remote Similarity	NPC84987
0.6667	Remote Similarity	NPC309034
0.6629	Remote Similarity	NPC232785
0.6629	Remote Similarity	NPC486139
0.6627	Remote Similarity	NPC250556
0.6598	Remote Similarity	NPC286809
0.6562	Remote Similarity	NPC474423
0.6552	Remote Similarity	NPC27363
0.6548	Remote Similarity	NPC305574
0.6517	Remote Similarity	NPC125077
0.6429	Remote Similarity	NPC77319
0.6429	Remote Similarity	NPC471351
0.6429	Remote Similarity	NPC471355
0.6404	Remote Similarity	NPC231518
0.6404	Remote Similarity	NPC488944
0.6386	Remote Similarity	NPC479356
0.6386	Remote Similarity	NPC479355
0.6374	Remote Similarity	NPC329986
0.6374	Remote Similarity	NPC140092
0.6341	Remote Similarity	NPC473852
0.6333	Remote Similarity	NPC208193
0.6322	Remote Similarity	NPC173555
0.6304	Remote Similarity	NPC486138
0.6304	Remote Similarity	NPC276838
0.6279	Remote Similarity	NPC193893
0.6277	Remote Similarity	NPC486136
0.622	Remote Similarity	NPC158344
0.6216	Remote Similarity	NPC268829
0.6216	Remote Similarity	NPC295110
0.6163	Remote Similarity	NPC483822
0.6163	Remote Similarity	NPC9499
0.6163	Remote Similarity	NPC471360
0.6163	Remote Similarity	NPC469751
0.6163	Remote Similarity	NPC471361
0.6163	Remote Similarity	NPC86159
0.6163	Remote Similarity	NPC469752
0.6163	Remote Similarity	NPC469754
0.6163	Remote Similarity	NPC70542
0.6092	Remote Similarity	NPC471354
0.6092	Remote Similarity	NPC27507
0.6087	Remote Similarity	NPC469749
0.6071	Remote Similarity	NPC219085
0.6024	Remote Similarity	NPC474418
0.6	Remote Similarity	NPC479360
0.6	Remote Similarity	NPC479359
0.6	Remote Similarity	NPC488943
0.6	Remote Similarity	NPC99080
0.6	Remote Similarity	NPC40749
0.6	Remote Similarity	NPC488942
0.5955	Remote Similarity	NPC5883
0.5934	Remote Similarity	NPC32793
0.5934	Remote Similarity	NPC116075
0.5895	Remote Similarity	NPC475219
0.587	Remote Similarity	NPC475629
0.5862	Remote Similarity	NPC83287
0.5859	Remote Similarity	NPC486150
0.5833	Remote Similarity	NPC488938
0.5833	Remote Similarity	NPC488937
0.5761	Remote Similarity	NPC475556
0.5761	Remote Similarity	NPC479353
0.5761	Remote Similarity	NPC479354
0.5761	Remote Similarity	NPC311706
0.5761	Remote Similarity	NPC486130
0.5758	Remote Similarity	NPC117445
0.5758	Remote Similarity	NPC308262
0.5699	Remote Similarity	NPC488941
0.5699	Remote Similarity	NPC488940
0.5699	Remote Similarity	NPC486127
0.5698	Remote Similarity	NPC486129
0.5644	Remote Similarity	NPC488945
0.5644	Remote Similarity	NPC488946
0.5632	Remote Similarity	NPC486126
0.5604	Remote Similarity	NPC103534
0.5604	Remote Similarity	NPC44899
0.5604	Remote Similarity	NPC304260
0.5604	Remote Similarity	NPC29639
0.5581	Remote Similarity	NPC479351
0.5581	Remote Similarity	NPC479352
0.5568	Remote Similarity	NPC10823
0.5568	Remote Similarity	NPC480908
0.5521	Remote Similarity	NPC146857
0.5521	Remote Similarity	NPC247190
0.5455	Remote Similarity	NPC34390
0.5444	Remote Similarity	NPC277374
0.5443	Remote Similarity	NPC222875
0.5443	Remote Similarity	NPC25177
0.5437	Remote Similarity	NPC488947
0.5435	Remote Similarity	NPC488935
0.5435	Remote Similarity	NPC488936
0.5408	Remote Similarity	NPC476221
0.5408	Remote Similarity	NPC477709
0.5408	Remote Similarity	NPC479357
0.5408	Remote Similarity	NPC486132
0.5408	Remote Similarity	NPC486131
0.5393	Remote Similarity	NPC243196
0.5393	Remote Similarity	NPC152615
0.5393	Remote Similarity	NPC604978
0.5385	Remote Similarity	NPC187302
0.5368	Remote Similarity	NPC264336
0.5368	Remote Similarity	NPC610296
0.5361	Remote Similarity	NPC488939
0.5354	Remote Similarity	NPC486128
0.5333	Remote Similarity	NPC146456
0.5333	Remote Similarity	NPC88668
0.5333	Remote Similarity	NPC180079
0.5316	Remote Similarity	NPC196931
0.5316	Remote Similarity	NPC480913
0.5281	Remote Similarity	NPC6108
0.5281	Remote Similarity	NPC89514
0.5281	Remote Similarity	NPC477580
0.5263	Remote Similarity	NPC608063
0.5169	Remote Similarity	NPC484211
0.5155	Remote Similarity	NPC59288
0.5146	Remote Similarity	NPC486140
0.5146	Remote Similarity	NPC329675
0.5146	Remote Similarity	NPC194716
0.5104	Remote Similarity	NPC486151
0.5096	Remote Similarity	NPC486133
0.5063	Remote Similarity	NPC97487

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC579794 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5739
0.1-0.2	3224
0.2-0.3	167
0.3-0.4	4
0.4-0.5	3
0.5-0.6	7
0.6-0.7	4
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
0.7625	Intermediate Similarity	NPD8294	Phase 4
0.7436	Intermediate Similarity	NPD7319	Approved
0.6705	Remote Similarity	NPD8377	Phase 4
0.6627	Remote Similarity	NPD7507	Pre-clinical
0.6404	Remote Similarity	NPD8033	Approved
0.6322	Remote Similarity	NPD8296	Phase 4
0.5862	Remote Similarity	NPD7327	Approved
0.5862	Remote Similarity	NPD7328	Phase 4
0.5862	Remote Similarity	NPD8335	Phase 4
0.5795	Remote Similarity	NPD8380	Approved
0.5579	Remote Similarity	NPD8378	Pre-clinical
0.5579	Remote Similarity	NPD8379	Approved
0.5238	Remote Similarity	NPD6940	Discontinued

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