NPASS Compound

Natural Product: NPC251417

Natural Product ID	NPC251417
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Moricandin
IUPAC Name	5-hydroxy-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
Synonyms	moricandin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL442686
PubChem CID	44575359
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 94 99 0 0 0 0 0 0 0 0999 V2000 8.3051 -4.1030 -1.6586 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3575 -4.1470 -0.1434 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2936 -3.0790 0.3287 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8194 -2.4758 1.6315 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4306 -1.9402 1.5405 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6996 -2.7209 0.4265 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0834 -4.0303 0.3943 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3415 -2.4982 0.5196 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5452 -1.6223 -0.1852 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0168 -0.7487 -1.1428 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1749 0.1228 -1.8315 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8187 0.1459 -1.5798 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3291 -0.7176 -0.6300 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1742 -1.5807 0.0505 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0488 -0.6784 -0.4101 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1923 0.1328 -1.0344 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2305 0.0344 -0.6678 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5273 -0.6507 0.5085 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7869 -0.8825 0.9365 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8556 -0.4289 0.1925 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5763 0.2624 -0.9928 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2767 0.4775 -1.3965 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6356 0.7259 -1.7520 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1328 -0.6494 0.5973 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6085 -1.3300 1.7020 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4623 -0.4353 2.5772 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9232 -0.5453 2.2875 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4199 -1.9605 2.2119 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2134 -2.9117 2.1961 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6905 -4.3099 1.8387 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5908 -4.7674 2.7789 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3120 -2.4660 1.2603 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2158 -2.2816 3.2826 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2008 0.2076 1.1541 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1828 -0.6487 3.9259 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6278 1.0149 -1.9809 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0057 1.0214 -2.2710 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4876 1.8024 -3.1396 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1481 1.9211 -2.6827 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2513 3.2788 -2.2515 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1757 4.2718 -3.3586 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2498 5.6634 -2.7540 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5963 5.7481 -2.0830 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7379 4.6367 -1.0401 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1561 4.6518 -0.4784 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2783 3.7982 0.6110 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3592 3.4087 -1.4644 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7198 6.9737 -1.4579 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1222 6.6560 -3.6938 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0291 4.1971 -4.0229 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6629 0.9993 -2.7937 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3787 -0.5926 1.1777 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6724 -1.4239 1.9599 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5848 -3.5882 0.5762 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9301 -3.2729 -2.0299 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2612 -3.9660 -1.9867 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7476 -5.0341 -2.0785 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8335 -5.1264 0.1689 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4458 -2.2788 -0.4521 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8915 -3.3017 2.3964 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9286 -2.0561 2.4998 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0753 -2.2205 -0.5067 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0651 -0.7267 -1.3769 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7796 -2.2605 0.8003 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7059 -1.0322 1.1387 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9429 -1.4297 1.8747 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0880 0.9925 -2.3359 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1339 1.5835 -1.5413 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8052 -1.7206 2.3483 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1605 0.6187 2.3464 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4539 -0.0259 3.1408 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9519 -2.1214 1.2433 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7863 -2.9534 3.2161 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1500 -4.2346 0.8264 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8274 -4.9790 1.7782 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1859 -4.8048 3.6594 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1504 -2.3863 2.9956 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5881 -0.3145 0.4331 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0280 -0.8281 4.4231 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6253 3.4625 -1.5613 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9624 4.1286 -4.1325 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5485 5.7008 -1.9786 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3771 5.6302 -2.8583 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0775 4.9477 -0.1994 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3834 5.6643 -0.1472 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8766 4.2667 -1.2531 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9744 3.0929 0.4784 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4863 6.8797 -0.5193 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1128 7.5210 -3.2290 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9596 3.7915 -4.9209 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5339 0.8714 -3.7848 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8420 -0.4633 0.3208 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2564 -0.5645 1.7801 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0417 -2.9878 1.2206 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 6 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 21 23 1 0 20 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 30 31 1 0 29 32 1 0 28 33 1 0 27 34 1 0 26 35 1 0 16 36 2 0 36 37 1 0 37 38 2 0 36 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 44 47 1 0 43 48 1 0 42 49 1 0 41 50 1 0 11 51 1 0 5 52 1 0 4 53 1 0 3 54 1 0 7 2 1 0 14 9 1 0 22 17 1 0 32 25 1 0 47 40 1 0 37 12 1 0 1 55 1 0 1 56 1 0 1 57 1 0 2 58 1 6 3 59 1 6 4 60 1 1 5 61 1 1 6 62 1 6 10 63 1 0 14 64 1 0 18 65 1 0 19 66 1 0 22 67 1 0 23 68 1 0 25 69 1 1 26 70 1 6 27 71 1 1 28 72 1 6 29 73 1 1 30 74 1 0 30 75 1 0 31 76 1 0 33 77 1 0 34 78 1 0 35 79 1 0 40 80 1 1 41 81 1 6 42 82 1 1 43 83 1 6 44 84 1 1 45 85 1 0 45 86 1 0 46 87 1 0 48 88 1 0 49 89 1 0 50 90 1 0 51 91 1 0 52 92 1 0 53 93 1 0 54 94 1 0 M END

Standard InCHIKey	CUNHEVJFIYAKHY-JFAQOVLHSA-N
Standard InCHI	InChI=1S/C33H40O21/c1-9-19(38)23(42)26(45)31(48-9)49-11-5-13(37)18-15(6-11)50-29(30(22(18)41)54-33-28(47)25(44)21(40)17(8-35)53-33)10-2-3-14(12(36)4-10)51-32-27(46)24(43)20(39)16(7-34)52-32/h2-6,9,16-17,19-21,23-28,31-40,42-47H,7-8H2,1H3/t9-,16+,17+,19-,20+,21+,23+,24-,25-,26+,27+,28+,31-,32+,33-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1cc(c2c(c1)oc(c1ccc(c(c1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)c(c2=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	772.21	Volume:	691.488 ? Van der Waals volume.
Dense:	1.117	LogP:	0.014 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.081 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.909 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	36.0
TPSA:	348.58 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	13.0	Rings:	6.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.097	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.381	Fsp³:	0.545
MCE-18:	154.294 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.647	Fluc inhibitor:	0.296 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.753 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.624 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.285	Promiscuous compounds:	0.603

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.002	MDCK Permeability:	-4.827
Pgp-inhibitor:	0.0	Pgp-substrate:	0.613
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):	0.999
20% Bioavailability (F20%):	0.095	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.001
Plasma Protein Binding (PPB):	76.024%	Volume Distribution (VD):	-0.177
Fu:	22.328% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.088
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.086
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):

0.716

Half-life (T1/2):

7.788

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.01
Human Hepatotoxicity (H-HT):	0.805	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.987	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.008	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.234	Drug-induced Nephrotoxicity:	0.944
Genotoxicity:	0.759	RPMI-8226 Immunitoxicity:	0.325
A549 Cytotoxicity:	0.788	Hek293 Cytotoxicity:	0.228
BCF:	0.323 ? 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:	2.73 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.558 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.455 ? 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
NPO14305	Moricandia arvensis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844940]
NPO14305	Moricandia arvensis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14305	Moricandia arvensis	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

Activity Type	# Activity
Activity	2
IC50	1

Activity Type	# Activity
Others	1
Non-molecular	2

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	1.23	mM	PMID[15844940]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	48.1	ug.mL-1	PMID[15844940]
NPT1	Others	Radical scavenging activity	n.a.	Activity	=	60.0	%	DrugMatrix in vivo data: Pathology

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 NPC251417 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	20319
0.1-0.2	25908
0.2-0.3	2470
0.3-0.4	651
0.4-0.5	300
0.5-0.6	141
0.6-0.7	42
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8553	High Similarity	NPC611303
0.8333	Intermediate Similarity	NPC605784
0.8101	Intermediate Similarity	NPC116458
0.8101	Intermediate Similarity	NPC246943
0.8026	Intermediate Similarity	NPC289667
0.7692	Intermediate Similarity	NPC136042
0.7468	Intermediate Similarity	NPC297987
0.7407	Intermediate Similarity	NPC60735
0.7407	Intermediate Similarity	NPC26230
0.7407	Intermediate Similarity	NPC285197
0.7386	Intermediate Similarity	NPC606657
0.7342	Intermediate Similarity	NPC249281
0.716	Intermediate Similarity	NPC84362
0.716	Intermediate Similarity	NPC271692
0.7108	Intermediate Similarity	NPC486578
0.7	Intermediate Similarity	NPC35119
0.6951	Remote Similarity	NPC46420
0.6905	Remote Similarity	NPC22832
0.6905	Remote Similarity	NPC120099
0.6905	Remote Similarity	NPC609478
0.6829	Remote Similarity	NPC158674
0.6813	Remote Similarity	NPC32641
0.6813	Remote Similarity	NPC256188
0.6809	Remote Similarity	NPC14187
0.6786	Remote Similarity	NPC219904
0.6778	Remote Similarity	NPC64425
0.6744	Remote Similarity	NPC276377
0.6706	Remote Similarity	NPC21666
0.6701	Remote Similarity	NPC480441
0.6634	Remote Similarity	NPC470719
0.6556	Remote Similarity	NPC150164
0.6531	Remote Similarity	NPC25523
0.6429	Remote Similarity	NPC64305
0.6333	Remote Similarity	NPC480466
0.6304	Remote Similarity	NPC186816
0.6279	Remote Similarity	NPC472459
0.6277	Remote Similarity	NPC72016
0.6235	Remote Similarity	NPC95090
0.6235	Remote Similarity	NPC27408
0.6136	Remote Similarity	NPC601144
0.6078	Remote Similarity	NPC470716
0.6064	Remote Similarity	NPC240306
0.6047	Remote Similarity	NPC145038
0.6047	Remote Similarity	NPC56077
0.6047	Remote Similarity	NPC281131
0.6047	Remote Similarity	NPC253662
0.6047	Remote Similarity	NPC179950
0.6047	Remote Similarity	NPC277205
0.6047	Remote Similarity	NPC37919
0.6047	Remote Similarity	NPC88789
0.6047	Remote Similarity	NPC189142
0.6047	Remote Similarity	NPC77660
0.6047	Remote Similarity	NPC491374
0.6044	Remote Similarity	NPC480463
0.6042	Remote Similarity	NPC5319
0.604	Remote Similarity	NPC470715
0.604	Remote Similarity	NPC164704
0.6023	Remote Similarity	NPC488071
0.598	Remote Similarity	NPC277532
0.5977	Remote Similarity	NPC27640
0.5962	Remote Similarity	NPC295625
0.5955	Remote Similarity	NPC243930
0.5955	Remote Similarity	NPC605067
0.5943	Remote Similarity	NPC470720
0.593	Remote Similarity	NPC127546
0.593	Remote Similarity	NPC261866
0.593	Remote Similarity	NPC39360
0.593	Remote Similarity	NPC57625
0.593	Remote Similarity	NPC77672
0.593	Remote Similarity	NPC133671
0.593	Remote Similarity	NPC19709
0.593	Remote Similarity	NPC135391
0.593	Remote Similarity	NPC29763
0.593	Remote Similarity	NPC173637
0.593	Remote Similarity	NPC78263
0.593	Remote Similarity	NPC210003
0.593	Remote Similarity	NPC317489
0.593	Remote Similarity	NPC250069
0.593	Remote Similarity	NPC238376
0.593	Remote Similarity	NPC223424
0.593	Remote Similarity	NPC600591
0.5909	Remote Similarity	NPC42773
0.5909	Remote Similarity	NPC59534
0.5909	Remote Similarity	NPC21100
0.5909	Remote Similarity	NPC45522
0.5889	Remote Similarity	NPC311830
0.5862	Remote Similarity	NPC265530
0.5862	Remote Similarity	NPC323593
0.5862	Remote Similarity	NPC203500
0.5849	Remote Similarity	NPC470717
0.5843	Remote Similarity	NPC191306
0.5824	Remote Similarity	NPC203050
0.5824	Remote Similarity	NPC488072
0.5824	Remote Similarity	NPC225434
0.5824	Remote Similarity	NPC601586
0.5814	Remote Similarity	NPC111929
0.5814	Remote Similarity	NPC320283
0.5814	Remote Similarity	NPC473043
0.5814	Remote Similarity	NPC331652
0.5814	Remote Similarity	NPC41121
0.5795	Remote Similarity	NPC305811
0.5795	Remote Similarity	NPC24043
0.5773	Remote Similarity	NPC209296
0.5773	Remote Similarity	NPC473327
0.5747	Remote Similarity	NPC19388
0.5747	Remote Similarity	NPC240431
0.5747	Remote Similarity	NPC55786
0.5747	Remote Similarity	NPC108831
0.5747	Remote Similarity	NPC182634
0.573	Remote Similarity	NPC325555
0.573	Remote Similarity	NPC226304
0.573	Remote Similarity	NPC599850
0.5714	Remote Similarity	NPC223747
0.5714	Remote Similarity	NPC607707
0.5632	Remote Similarity	NPC135599
0.5632	Remote Similarity	NPC73855
0.5632	Remote Similarity	NPC113968
0.5632	Remote Similarity	NPC328940
0.5632	Remote Similarity	NPC277174
0.5632	Remote Similarity	NPC606877
0.5619	Remote Similarity	NPC470718
0.5618	Remote Similarity	NPC488080
0.5618	Remote Similarity	NPC349108
0.5618	Remote Similarity	NPC169977
0.5604	Remote Similarity	NPC101026
0.5604	Remote Similarity	NPC488077
0.5591	Remote Similarity	NPC265115
0.5513	Remote Similarity	NPC270620
0.551	Remote Similarity	NPC483414
0.5506	Remote Similarity	NPC8573
0.5506	Remote Similarity	NPC234739
0.5495	Remote Similarity	NPC307938
0.5478	Remote Similarity	NPC223860
0.5463	Remote Similarity	NPC198199
0.5455	Remote Similarity	NPC160515
0.5444	Remote Similarity	NPC603655
0.5412	Remote Similarity	NPC134819
0.54	Remote Similarity	NPC142142
0.54	Remote Similarity	NPC486577
0.5354	Remote Similarity	NPC483415
0.5347	Remote Similarity	NPC475382
0.5341	Remote Similarity	NPC67037
0.5341	Remote Similarity	NPC255615
0.5333	Remote Similarity	NPC197896
0.5333	Remote Similarity	NPC313163
0.5319	Remote Similarity	NPC267254
0.5319	Remote Similarity	NPC355481
0.5315	Remote Similarity	NPC120952
0.5306	Remote Similarity	NPC115674
0.53	Remote Similarity	NPC483416
0.5294	Remote Similarity	NPC191154
0.5288	Remote Similarity	NPC121703
0.5275	Remote Similarity	NPC73511
0.5269	Remote Similarity	NPC148710
0.5268	Remote Similarity	NPC192539
0.5258	Remote Similarity	NPC471748
0.5243	Remote Similarity	NPC135358
0.5227	Remote Similarity	NPC288084
0.5222	Remote Similarity	NPC58053
0.5222	Remote Similarity	NPC254306
0.5222	Remote Similarity	NPC348541
0.5213	Remote Similarity	NPC206123
0.5208	Remote Similarity	NPC278419
0.5208	Remote Similarity	NPC179198
0.5204	Remote Similarity	NPC22062
0.5204	Remote Similarity	NPC65003
0.5204	Remote Similarity	NPC473634
0.5204	Remote Similarity	NPC155877
0.5204	Remote Similarity	NPC138811
0.5204	Remote Similarity	NPC156869
0.5204	Remote Similarity	NPC605592
0.52	Remote Similarity	NPC470443
0.5196	Remote Similarity	NPC195257
0.5196	Remote Similarity	NPC256760
0.5196	Remote Similarity	NPC76831
0.5161	Remote Similarity	NPC80140
0.5155	Remote Similarity	NPC29958
0.5155	Remote Similarity	NPC139320
0.5109	Remote Similarity	NPC245014
0.5109	Remote Similarity	NPC186807
0.5109	Remote Similarity	NPC58716
0.5109	Remote Similarity	NPC181712
0.5102	Remote Similarity	NPC275454
0.5102	Remote Similarity	NPC163242
0.5102	Remote Similarity	NPC272068
0.5102	Remote Similarity	NPC67105
0.51	Remote Similarity	NPC488073
0.5056	Remote Similarity	NPC34531
0.5055	Remote Similarity	NPC45618
0.5055	Remote Similarity	NPC143851
0.5052	Remote Similarity	NPC8856
0.5051	Remote Similarity	NPC203259
0.5051	Remote Similarity	NPC33054
0.5051	Remote Similarity	NPC210073
0.5051	Remote Similarity	NPC176740
0.5051	Remote Similarity	NPC471725
0.5051	Remote Similarity	NPC134532
0.5051	Remote Similarity	NPC602582
0.5049	Remote Similarity	NPC473071

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC251417 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5134
0.1-0.2	3947
0.2-0.3	58
0.3-0.4	3
0.4-0.5	3
0.5-0.6	4
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
0.6042	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD7251	Phase 2
0.59	Remote Similarity	NPD7808	Phase 3
0.5773	Remote Similarity	NPD7054	Phase 4
0.5051	Remote Similarity	NPD6797	Phase 2

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