NPASS Compound

Natural Product: NPC579251

Natural Product ID	NPC579251
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NS00093812
IUPAC Name	3-[14-hydroxy-10,13-dimethyl-3-[3,4,5-trihydroxy-6-[(4,5,6-trihydroxy-2-methyl-tetrahydropyran-3-yl)oxymethyl]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 102108 0 0 0 0 0 0 0 0999 V2000 8.1602 3.1263 -0.1897 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6444 2.2425 -1.2875 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4493 2.2029 -2.3942 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4387 1.2350 -2.3413 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0225 0.1531 -3.1230 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6832 0.7133 -0.9598 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6807 -0.2801 -1.0719 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4288 0.0043 -0.4916 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6033 -0.2649 0.8647 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2446 0.8511 -0.7834 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4916 1.0324 0.3422 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1560 0.7418 0.2656 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8040 -0.6963 -0.0421 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4736 -0.7872 -0.1036 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6904 -1.4472 0.7445 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5425 -0.6810 0.9534 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3632 -1.2598 0.5739 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1782 -0.3961 -0.5711 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5528 -0.7772 -1.0109 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4478 -1.1391 0.1426 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4777 -2.6488 0.2477 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8059 -0.4962 1.3646 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8309 -0.2934 2.4274 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6935 0.8987 1.9762 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0103 0.7941 0.5294 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8513 -0.6547 0.0477 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4034 -0.7019 -1.3599 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9053 -0.5667 -1.3056 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3825 0.4025 -0.2921 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9931 -0.2008 0.9256 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3521 1.4261 -0.8302 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6652 0.9677 -1.2221 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1505 1.1325 -2.4706 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4897 0.5810 -2.5709 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2391 0.5566 -3.5805 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8205 0.0722 -1.3467 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7074 0.2640 -0.4715 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3540 2.4566 0.3100 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9989 2.2863 1.0025 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2670 1.3838 0.0548 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0352 2.1129 -1.1127 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5653 -1.2023 1.7882 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3725 -1.8359 2.0039 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6392 -0.7786 2.8752 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6245 -2.5852 1.5994 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2518 -3.1878 2.6668 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5320 -1.6479 0.8392 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4343 -2.4485 0.1474 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2310 2.5723 0.7876 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4502 3.9737 0.0462 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1173 3.6353 -0.4445 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6650 2.6940 -1.6319 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3721 1.6596 -2.7580 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2411 0.3008 -4.0790 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0740 1.4449 -0.2499 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4047 -1.0040 -1.6666 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4034 -0.9674 -1.0448 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1137 0.4136 1.3474 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6301 0.4322 -1.6216 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7009 1.0958 1.2188 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7071 1.4286 -0.5116 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1939 -0.8744 -1.0911 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3174 -2.4120 0.2766 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4517 -2.2743 0.1492 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0316 0.6792 -0.3700 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5116 -0.6252 -1.4320 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9924 0.1466 -1.4884 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5965 -1.5557 -1.7806 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4927 -3.0411 -0.0459 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7750 -3.1305 -0.4920 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2866 -3.0300 1.2579 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4892 0.5422 1.0454 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5018 -1.1482 2.5149 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3890 -0.1059 3.4261 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5222 1.0435 2.6646 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0119 1.7850 2.1630 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1523 1.3168 -0.0046 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4855 -1.3424 0.6526 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1773 -1.7151 -1.7503 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9377 0.0265 -2.0472 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3891 -1.5641 -1.0901 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2252 -0.2698 -2.3465 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2971 -0.2650 1.7905 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2797 -1.2314 0.7039 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8653 0.3610 1.2770 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7987 1.9120 -1.6918 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6352 1.6041 -3.2954 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0202 0.8772 0.3929 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4085 -0.7409 -0.0900 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1993 2.3417 0.9867 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3232 3.4723 -0.1707 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2426 1.8322 1.9817 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5104 3.2592 1.1656 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0937 2.4006 -1.1842 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1194 -0.5663 2.6112 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7200 -2.1873 2.2459 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7912 -2.5658 2.6176 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8846 -0.6243 3.4666 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2963 -3.3866 0.9035 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6528 -3.3576 3.4110 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1117 -1.0861 1.5952 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0934 -2.8395 -0.6709 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 4 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 1 0 31 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 22 42 1 0 15 43 1 0 43 44 1 0 43 45 1 0 45 46 1 0 45 47 1 0 47 48 1 0 10 2 1 0 47 13 1 0 42 17 1 0 26 20 1 0 40 29 1 0 40 25 1 0 37 32 1 0 1 49 1 0 1 50 1 0 1 51 1 0 2 52 1 0 4 53 1 0 5 54 1 0 6 55 1 0 7 56 1 0 8 57 1 0 9 58 1 0 10 59 1 0 12 60 1 0 12 61 1 0 13 62 1 0 15 63 1 0 17 64 1 0 18 65 1 0 18 66 1 0 19 67 1 0 19 68 1 0 21 69 1 0 21 70 1 0 21 71 1 0 22 72 1 0 23 73 1 0 23 74 1 0 24 75 1 0 24 76 1 0 25 77 1 0 26 78 1 0 27 79 1 0 27 80 1 0 28 81 1 0 28 82 1 0 30 83 1 0 30 84 1 0 30 85 1 0 31 86 1 0 33 87 1 0 37 88 1 0 37 89 1 0 38 90 1 0 38 91 1 0 39 92 1 0 39 93 1 0 41 94 1 0 42 95 1 0 42 96 1 0 43 97 1 0 44 98 1 0 45 99 1 0 46100 1 0 47101 1 0 48102 1 0 M END

Standard InCHIKey	ZBNBSIKYLONGAI-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C35H54O13/c1-16-30(27(39)28(40)31(42)46-16)45-15-23-25(37)26(38)29(41)32(48-23)47-19-6-9-33(2)18(13-19)4-5-22-21(33)7-10-34(3)20(8-11-35(22,34)43)17-12-24(36)44-14-17/h12,16,18-23,25-32,37-43H,4-11,13-15H2,1-3H3
SMILES	CC1OC(O)C(O)C(O)C1OCC1OC(OC2CCC3(C)C(CCC4C3CCC3(C)C(C5=CC(=O)OC5)CCC43O)C2)C(O)C(O)C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	682.36	Volume:	663.021 ? Van der Waals volume.
Dense:	1.029	LogP:	0.687 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.348 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.28 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	38.0
TPSA:	204.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.149	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.626	Fsp³:	0.914
MCE-18:	133.284 ? 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:	0.011	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.025 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.161 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.084	Promiscuous compounds:	0.009

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.306	MDCK Permeability:	-4.957
Pgp-inhibitor:	0.0	Pgp-substrate:	0.709
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):	0.835
20% Bioavailability (F20%):	0.023	30% Bioavailability (F30%):	0.406
50% Bioavailability (F50%):	0.915

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017	MRP1:	0.998
Plasma Protein Binding (PPB):	57.592%	Volume Distribution (VD):	-0.488
Fu:	38.359% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.118	BCRP inhibitor:	0.0
BSEP inhibitor:	0.123

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.046	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.937	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.003	CYP2C8-inhibitor:	0.005
HLM stability:	0.001 ? 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):

1.202

Half-life (T1/2):

3.531

ADMET: Toxicity

hERG Blockers:	0.205	hERG Blockers (10um):	0.733
Human Hepatotoxicity (H-HT):	0.7	Drug-induced Liver Injury (DILI):	0.483
AMES Toxicity:	0.847	Rat Oral Acute Toxicity:	0.789
Maximum Recommended Daily Dose:	0.989	Skin Sensitization:	0.361
Carcinogencity:	0.402	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.292
Drug-induced Neurotoxicity:	0.203	Ototoxicity:	0.997
Hematotoxicity:	0.066	Drug-induced Nephrotoxicity:	0.059
Genotoxicity:	0.33	RPMI-8226 Immunitoxicity:	0.442
A549 Cytotoxicity:	0.269	Hek293 Cytotoxicity:	0.931
BCF:	0.774 ? 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:	3.936 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.895 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.304 ? 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
NPO56013	Erysimum cheiri (L.) Crantz	Genus	Brassicaceae	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 NPC579251 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	16524
0.1-0.2	28800
0.2-0.3	4008
0.3-0.4	316
0.4-0.5	70
0.5-0.6	74
0.6-0.7	54
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
0.7556	Intermediate Similarity	NPC30483
0.7556	Intermediate Similarity	NPC470897
0.7529	Intermediate Similarity	NPC99620
0.7473	Intermediate Similarity	NPC236973
0.7356	Intermediate Similarity	NPC5311
0.7143	Intermediate Similarity	NPC486144
0.7143	Intermediate Similarity	NPC486145
0.7143	Intermediate Similarity	NPC486147
0.7143	Intermediate Similarity	NPC475590
0.7143	Intermediate Similarity	NPC486148
0.6875	Remote Similarity	NPC486143
0.6875	Remote Similarity	NPC486142
0.6875	Remote Similarity	NPC486149
0.6667	Remote Similarity	NPC475419
0.6602	Remote Similarity	NPC474908
0.6602	Remote Similarity	NPC486134
0.6602	Remote Similarity	NPC486141
0.6596	Remote Similarity	NPC72260
0.6593	Remote Similarity	NPC469750
0.6571	Remote Similarity	NPC474423
0.6562	Remote Similarity	NPC32177
0.6562	Remote Similarity	NPC292467
0.6562	Remote Similarity	NPC469756
0.6562	Remote Similarity	NPC275901
0.6522	Remote Similarity	NPC76572
0.6522	Remote Similarity	NPC193382
0.6495	Remote Similarity	NPC188234
0.6413	Remote Similarity	NPC77299
0.6413	Remote Similarity	NPC480906
0.64	Remote Similarity	NPC486146
0.6374	Remote Similarity	NPC471633
0.6346	Remote Similarity	NPC120390
0.6346	Remote Similarity	NPC74259
0.6344	Remote Similarity	NPC199428
0.6344	Remote Similarity	NPC109448
0.6344	Remote Similarity	NPC310341
0.6344	Remote Similarity	NPC480914
0.6311	Remote Similarity	NPC486136
0.6304	Remote Similarity	NPC196429
0.6296	Remote Similarity	NPC286809
0.625	Remote Similarity	NPC480907
0.617	Remote Similarity	NPC84949
0.617	Remote Similarity	NPC480562
0.617	Remote Similarity	NPC74945
0.617	Remote Similarity	NPC31354
0.617	Remote Similarity	NPC69576
0.6064	Remote Similarity	NPC157376
0.6064	Remote Similarity	NPC142066
0.6064	Remote Similarity	NPC603972
0.6058	Remote Similarity	NPC479360
0.6058	Remote Similarity	NPC479359
0.6042	Remote Similarity	NPC484202
0.6042	Remote Similarity	NPC93883
0.604	Remote Similarity	NPC125077
0.604	Remote Similarity	NPC55532
0.604	Remote Similarity	NPC486135
0.604	Remote Similarity	NPC486137
0.6022	Remote Similarity	NPC99728
0.6022	Remote Similarity	NPC87250
0.6022	Remote Similarity	NPC244402
0.6022	Remote Similarity	NPC50305
0.6	Remote Similarity	NPC480910
0.6	Remote Similarity	NPC240070
0.6	Remote Similarity	NPC480909
0.598	Remote Similarity	NPC232785
0.598	Remote Similarity	NPC486139
0.5895	Remote Similarity	NPC17896
0.5895	Remote Similarity	NPC469755
0.5895	Remote Similarity	NPC284406
0.5895	Remote Similarity	NPC197707
0.5895	Remote Similarity	NPC251866
0.5882	Remote Similarity	NPC208193
0.5842	Remote Similarity	NPC32793
0.5842	Remote Similarity	NPC116075
0.5789	Remote Similarity	NPC84987
0.5784	Remote Similarity	NPC231518
0.5784	Remote Similarity	NPC488944
0.578	Remote Similarity	NPC486150
0.5743	Remote Similarity	NPC40749
0.5729	Remote Similarity	NPC480915
0.5727	Remote Similarity	NPC488945
0.5727	Remote Similarity	NPC488946
0.5619	Remote Similarity	NPC329986
0.5619	Remote Similarity	NPC140092
0.5566	Remote Similarity	NPC486138
0.5566	Remote Similarity	NPC276838
0.5556	Remote Similarity	NPC179412
0.5556	Remote Similarity	NPC471356
0.5556	Remote Similarity	NPC471353
0.5545	Remote Similarity	NPC173555
0.5534	Remote Similarity	NPC475556
0.5534	Remote Similarity	NPC311706
0.5514	Remote Similarity	NPC479357
0.5514	Remote Similarity	NPC475219
0.5514	Remote Similarity	NPC486131
0.55	Remote Similarity	NPC193893
0.5481	Remote Similarity	NPC264336
0.5481	Remote Similarity	NPC475629
0.5463	Remote Similarity	NPC486128
0.5463	Remote Similarity	NPC488943
0.5463	Remote Similarity	NPC488942
0.5455	Remote Similarity	NPC250556
0.5417	Remote Similarity	NPC158344
0.5405	Remote Similarity	NPC117445
0.5405	Remote Similarity	NPC308262
0.54	Remote Similarity	NPC305574
0.5398	Remote Similarity	NPC488947
0.5357	Remote Similarity	NPC486133
0.5306	Remote Similarity	NPC219085
0.5268	Remote Similarity	NPC194716
0.5253	Remote Similarity	NPC479356
0.5253	Remote Similarity	NPC479355
0.5248	Remote Similarity	NPC483822
0.5238	Remote Similarity	NPC479353
0.5238	Remote Similarity	NPC479354
0.5238	Remote Similarity	NPC486130
0.5234	Remote Similarity	NPC469749
0.5204	Remote Similarity	NPC473852
0.5189	Remote Similarity	NPC488941
0.5189	Remote Similarity	NPC488940
0.5189	Remote Similarity	NPC486127
0.5182	Remote Similarity	NPC488938
0.5182	Remote Similarity	NPC488937
0.5169	Remote Similarity	NPC268829
0.5169	Remote Similarity	NPC295110
0.5152	Remote Similarity	NPC309034
0.5149	Remote Similarity	NPC77319
0.5149	Remote Similarity	NPC471351
0.5149	Remote Similarity	NPC471355
0.5143	Remote Similarity	NPC27363
0.514	Remote Similarity	NPC59288
0.51	Remote Similarity	NPC99080
0.5094	Remote Similarity	NPC608063
0.5091	Remote Similarity	NPC486132
0.5049	Remote Similarity	NPC471354
0.5049	Remote Similarity	NPC27507
0.5047	Remote Similarity	NPC610296
0.5046	Remote Similarity	NPC146857

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC579251 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6416
0.1-0.2	2651
0.2-0.3	66
0.3-0.4	2
0.4-0.5	5
0.5-0.6	8
0.6-0.7	2
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
0.6596	Remote Similarity	NPD8294	Phase 4
0.62	Remote Similarity	NPD8377	Phase 4
0.5895	Remote Similarity	NPD7319	Approved
0.5784	Remote Similarity	NPD8033	Approved
0.5545	Remote Similarity	NPD8296	Phase 4
0.5455	Remote Similarity	NPD7507	Pre-clinical
0.5455	Remote Similarity	NPD8335	Phase 4
0.54	Remote Similarity	NPD8380	Approved
0.5234	Remote Similarity	NPD8378	Pre-clinical
0.5234	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