NPASS Compound

Natural Product: NPC514882

Natural Product ID	NPC514882
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-[(2~{S},3~{R},4~{R},5~{S},6~{S})-6-[[(2~{R},3~{R},4~{S})-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]oxymethyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-7-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	3-[(2~{S},3~{R},4~{R},5~{S},6~{S})-6-[[(2~{R},3~{R},4~{S})-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]oxymethyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-7-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-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 93 98 0 0 0 0 0 0 0 0999 V2000 -2.0836 6.4038 3.4929 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0892 6.7753 2.5765 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5500 5.9451 1.6304 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9157 4.6312 1.4396 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3152 3.8309 0.4478 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8183 2.4843 0.2639 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0652 1.4654 -0.2086 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2050 1.4700 -0.5766 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1022 1.5684 -1.5619 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4610 0.2768 -2.0964 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2147 -0.4592 -1.2383 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5044 -0.9893 -1.8897 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1156 -1.7634 -0.9068 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3217 -2.3318 -1.3256 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0816 -3.7090 -1.3606 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1797 -4.3793 -0.9035 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0822 -3.4363 -0.1840 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1910 -3.7378 1.1985 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5000 -3.5313 -0.7170 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9360 -4.8497 -0.4740 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4603 -2.0874 -0.4143 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4517 -1.2665 -0.9427 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5336 0.1797 0.0864 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4076 -0.6494 0.8164 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1264 1.5401 -0.1078 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4834 1.4924 -0.4771 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3989 2.2636 -1.2148 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2134 2.3495 -2.3636 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7067 0.1836 -0.3315 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0387 -0.7833 -0.7708 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0121 0.0542 0.0284 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6525 -1.1881 -0.0866 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9347 -2.2878 -0.5728 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9742 -1.3109 0.2791 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7037 -0.2502 0.7610 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0337 -0.3978 1.1220 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8411 -1.5010 0.9662 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.9229 -1.2010 0.0982 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2777 -2.4278 -0.4588 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3407 -2.2475 -1.4928 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8053 -3.2989 0.6599 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.0345 -3.8642 0.3764 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8324 -2.5582 1.9764 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.7521 -1.5060 1.9715 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4502 -2.0348 2.2561 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6533 -3.0775 2.7091 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0394 0.9560 0.8595 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7133 1.1402 0.5058 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1171 2.2934 0.6085 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6327 4.4349 -0.3002 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0282 5.7579 -0.1359 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4420 6.5142 0.8243 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7830 7.8545 1.0551 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9639 5.9155 3.0743 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4902 7.3368 4.0120 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5903 5.8345 4.3266 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 4.1801 2.0631 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6693 2.0569 -2.4516 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5869 -1.3716 -0.9705 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1203 -0.2120 -2.3247 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1708 -1.6798 -2.6988 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5896 -1.9856 -2.3652 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6415 -4.9163 -1.7488 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7918 -5.1065 -0.1277 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6328 -2.9404 1.5862 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5984 -3.2850 -1.7712 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1245 -2.8650 -0.0746 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8989 -5.0826 0.4799 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1391 -1.7274 0.6021 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4315 -0.3644 -0.5038 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6397 0.2749 0.7384 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1248 -0.8028 1.7364 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0754 2.1386 0.8539 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7795 2.4083 -0.7259 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2493 3.2971 -0.8660 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5821 2.4428 -3.1251 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4514 -2.9231 -1.1677 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3947 -2.2964 0.1636 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2884 -2.3210 0.4471 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3355 -2.8408 -0.8957 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2004 -1.7351 -1.0282 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6103 -3.2210 -1.9587 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9844 -1.6179 -2.3406 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0680 -4.1385 0.8004 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7814 -3.4558 0.8779 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0846 -3.3197 2.7491 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3814 -0.6917 2.4289 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4841 -1.1985 2.9716 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7266 -2.9440 2.3459 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5669 1.8230 1.2344 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0925 3.9220 -1.1179 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7990 6.2136 -0.7511 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1740 8.4587 0.3440 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 2 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 0 15 16 1 0 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 17 21 1 0 21 22 1 0 11 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 7 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 43 45 1 0 45 46 1 0 35 47 1 0 47 48 2 0 48 49 1 0 5 50 2 0 50 51 1 0 51 52 2 0 52 53 1 0 52 3 1 0 49 6 1 0 27 9 1 0 48 31 1 0 21 14 1 0 45 37 1 0 1 54 1 0 1 55 1 0 1 56 1 0 4 57 1 0 9 58 1 6 11 59 1 1 12 60 1 0 12 61 1 0 14 62 1 6 16 63 1 0 16 64 1 0 18 65 1 0 19 66 1 0 19 67 1 0 20 68 1 0 21 69 1 1 22 70 1 0 23 71 1 1 24 72 1 0 25 73 1 1 26 74 1 0 27 75 1 1 28 76 1 0 33 77 1 0 34 78 1 0 37 79 1 6 39 80 1 6 40 81 1 0 40 82 1 0 40 83 1 0 41 84 1 1 42 85 1 0 43 86 1 1 44 87 1 0 45 88 1 1 46 89 1 0 47 90 1 0 50 91 1 0 51 92 1 0 53 93 1 0 M END

Standard InCHIKey	IMCHSJLXDHJNGT-CDZZHRQNSA-N
Standard InCHI	InChI=1S/C33H40O20/c1-11-20(37)23(40)25(42)30(49-11)50-13-6-15(36)19-17(7-13)51-27(12-3-4-14(35)16(5-12)46-2)28(22(19)39)53-31-26(43)24(41)21(38)18(52-31)8-47-32-29(44)33(45,9-34)10-48-32/h3-7,11,18,20-21,23-26,29-32,34-38,40-45H,8-10H2,1-2H3/t11-,18+,20+,21-,23+,24-,25-,26-,29+,30+,31+,32-,33+/m1/s1
SMILES	COC1=CC(C2=C(O[C@@H]3O[C@@H](CO[C@@H]4OC[C@@](O)(CO)[C@H]4O)[C@@H](O)[C@@H](O)[C@H]3O)C(=O)C3=C(O)C=C(O[C@@H]4O[C@H](C)[C@H](O)[C@H](O)[C@H]4O)C=C3O2)=CC=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	756.21	Volume:	682.698 ? Van der Waals volume.
Dense:	1.108	LogP:	1.122 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.482 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.332 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	35.0
TPSA:	317.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.097	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.381	Fsp³:	0.545
MCE-18:	152.608 ? 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:	0.605	Fluc inhibitor:	0.272 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.777 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.561 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.07	Promiscuous compounds:	0.528

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.508	MDCK Permeability:	-5.287
Pgp-inhibitor:	0.0	Pgp-substrate:	0.97
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):	0.734
20% Bioavailability (F20%):	0.175	30% Bioavailability (F30%):	0.832
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.033
Plasma Protein Binding (PPB):	80.633%	Volume Distribution (VD):	-0.173
Fu:	18.852% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.981
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.57
BSEP inhibitor:	0.036

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:	0.262
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.344
HLM stability:	0.004 ? 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):

1.159

Half-life (T1/2):

4.424

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.105
Human Hepatotoxicity (H-HT):	0.661	Drug-induced Liver Injury (DILI):	0.819
AMES Toxicity:	0.954	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.008	Skin Sensitization:	1.0
Carcinogencity:	0.033	Eye Corrosion:	0.0
Eye Irritation:	0.019	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.982
Hematotoxicity:	0.22	Drug-induced Nephrotoxicity:	0.591
Genotoxicity:	0.32	RPMI-8226 Immunitoxicity:	0.156
A549 Cytotoxicity:	0.28	Hek293 Cytotoxicity:	0.375
BCF:	0.367 ? 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:	2.904 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.593 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.649 ? 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
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35357239]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	twig	n.a.	PMID[9179367]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7808	Viscum album	Species	Viscaceae	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 NPC514882 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	21058
0.1-0.2	25646
0.2-0.3	2290
0.3-0.4	437
0.4-0.5	289
0.5-0.6	111
0.6-0.7	19
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
0.7216	Intermediate Similarity	NPC186816
0.7113	Intermediate Similarity	NPC150164
0.703	Intermediate Similarity	NPC476472
0.703	Intermediate Similarity	NPC294815
0.703	Intermediate Similarity	NPC16194
0.6733	Remote Similarity	NPC65711
0.6596	Remote Similarity	NPC46420
0.6596	Remote Similarity	NPC271692
0.6458	Remote Similarity	NPC611303
0.6429	Remote Similarity	NPC276377
0.6383	Remote Similarity	NPC249281
0.6327	Remote Similarity	NPC223747
0.6311	Remote Similarity	NPC153755
0.6296	Remote Similarity	NPC121703
0.625	Remote Similarity	NPC470443
0.619	Remote Similarity	NPC72016
0.6176	Remote Similarity	NPC67105
0.6162	Remote Similarity	NPC116458
0.6162	Remote Similarity	NPC246943
0.6162	Remote Similarity	NPC605784
0.6146	Remote Similarity	NPC158674
0.6038	Remote Similarity	NPC209296
0.6	Remote Similarity	NPC126784
0.6	Remote Similarity	NPC241423
0.5982	Remote Similarity	NPC480441
0.5982	Remote Similarity	NPC25523
0.5981	Remote Similarity	NPC142142
0.598	Remote Similarity	NPC251417
0.5962	Remote Similarity	NPC210073
0.5905	Remote Similarity	NPC473571
0.5905	Remote Similarity	NPC110941
0.5888	Remote Similarity	NPC473327
0.5888	Remote Similarity	NPC606657
0.5865	Remote Similarity	NPC173582
0.5865	Remote Similarity	NPC44931
0.5865	Remote Similarity	NPC265885
0.5865	Remote Similarity	NPC181465
0.5865	Remote Similarity	NPC215710
0.5865	Remote Similarity	NPC473438
0.5865	Remote Similarity	NPC253788
0.5856	Remote Similarity	NPC89052
0.5833	Remote Similarity	NPC486577
0.581	Remote Similarity	NPC22062
0.581	Remote Similarity	NPC203259
0.581	Remote Similarity	NPC473634
0.581	Remote Similarity	NPC33054
0.581	Remote Similarity	NPC176740
0.581	Remote Similarity	NPC471725
0.581	Remote Similarity	NPC134532
0.581	Remote Similarity	NPC138811
0.581	Remote Similarity	NPC602582
0.5789	Remote Similarity	NPC277532
0.5752	Remote Similarity	NPC173837
0.5714	Remote Similarity	NPC227508
0.5657	Remote Similarity	NPC297987
0.5657	Remote Similarity	NPC136042
0.5636	Remote Similarity	NPC473073
0.5631	Remote Similarity	NPC203050
0.5631	Remote Similarity	NPC488072
0.5631	Remote Similarity	NPC225434
0.56	Remote Similarity	NPC84362
0.5596	Remote Similarity	NPC32641
0.5596	Remote Similarity	NPC256188
0.5596	Remote Similarity	NPC35119
0.5583	Remote Similarity	NPC209550
0.5565	Remote Similarity	NPC217520
0.5565	Remote Similarity	NPC303694
0.5556	Remote Similarity	NPC488073
0.5556	Remote Similarity	NPC238376
0.5556	Remote Similarity	NPC488074
0.5545	Remote Similarity	NPC59534
0.5537	Remote Similarity	NPC192539
0.5534	Remote Similarity	NPC311830
0.5514	Remote Similarity	NPC65563
0.5514	Remote Similarity	NPC470949
0.5487	Remote Similarity	NPC14187
0.5481	Remote Similarity	NPC601586
0.5472	Remote Similarity	NPC471079
0.547	Remote Similarity	NPC139571
0.5446	Remote Similarity	NPC27640
0.5437	Remote Similarity	NPC101026
0.5437	Remote Similarity	NPC488077
0.5421	Remote Similarity	NPC67326
0.5421	Remote Similarity	NPC39834
0.5413	Remote Similarity	NPC240306
0.54	Remote Similarity	NPC289667
0.54	Remote Similarity	NPC108831
0.54	Remote Similarity	NPC182634
0.5385	Remote Similarity	NPC78326
0.5372	Remote Similarity	NPC488079
0.537	Remote Similarity	NPC156869
0.5327	Remote Similarity	NPC609888
0.531	Remote Similarity	NPC235575
0.531	Remote Similarity	NPC470445
0.5294	Remote Similarity	NPC305811
0.5285	Remote Similarity	NPC175429
0.5278	Remote Similarity	NPC275454
0.5263	Remote Similarity	NPC470446
0.5263	Remote Similarity	NPC135358
0.5248	Remote Similarity	NPC19709
0.5229	Remote Similarity	NPC303913
0.5221	Remote Similarity	NPC195257
0.5221	Remote Similarity	NPC470447
0.5221	Remote Similarity	NPC220173
0.5203	Remote Similarity	NPC138990
0.5192	Remote Similarity	NPC219904
0.5179	Remote Similarity	NPC473623
0.5175	Remote Similarity	NPC101636
0.5175	Remote Similarity	NPC470449
0.5149	Remote Similarity	NPC111929
0.5149	Remote Similarity	NPC320283
0.5149	Remote Similarity	NPC331652
0.5149	Remote Similarity	NPC41121
0.5146	Remote Similarity	NPC349108
0.5143	Remote Similarity	NPC601144
0.514	Remote Similarity	NPC116864
0.514	Remote Similarity	NPC244776
0.514	Remote Similarity	NPC265115
0.5135	Remote Similarity	NPC64425
0.5133	Remote Similarity	NPC488089
0.5133	Remote Similarity	NPC600130
0.5128	Remote Similarity	NPC189564
0.5098	Remote Similarity	NPC127546
0.5098	Remote Similarity	NPC57625
0.5098	Remote Similarity	NPC173637
0.5098	Remote Similarity	NPC317489
0.5098	Remote Similarity	NPC223424
0.5098	Remote Similarity	NPC600591
0.5094	Remote Similarity	NPC206123
0.5085	Remote Similarity	NPC292019
0.5085	Remote Similarity	NPC202908
0.5085	Remote Similarity	NPC480796
0.5049	Remote Similarity	NPC265530
0.5046	Remote Similarity	NPC480466
0.5044	Remote Similarity	NPC229409

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC514882 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5716
0.1-0.2	3394
0.2-0.3	32
0.3-0.4	2
0.4-0.5	2
0.5-0.6	1
0.6-0.7	3
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
0.6699	Remote Similarity	NPD7251	Phase 2
0.6449	Remote Similarity	NPD7808	Phase 3
0.6038	Remote Similarity	NPD7054	Phase 4
0.581	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