NPASS Compound

Natural Product: NPC549374

Natural Product ID	NPC549374
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~{S},5~{R},6~{R})-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-7-methoxy-2-[4-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]chromen-4-one
IUPAC Name	3-[(2~{S},3~{R},4~{S},5~{R},6~{R})-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-7-methoxy-2-[4-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]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 96101 0 0 0 0 0 0 0 0999 V2000 -0.5317 9.8511 -0.0170 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2895 8.7037 0.0185 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2669 7.4303 0.0588 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6458 7.3054 0.0638 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2241 6.0523 0.1036 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6232 5.9552 0.1077 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4206 4.9289 0.1382 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0047 3.6976 0.1744 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2567 3.5594 0.1798 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1758 2.5632 0.2072 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9032 1.3674 0.2304 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2761 0.7480 -0.9989 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2468 1.6367 -1.5405 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6269 1.2594 -2.8088 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5759 2.3118 -3.3693 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0025 1.9958 -4.6554 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3991 -0.0235 -2.7324 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4983 0.0662 -1.8815 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4107 -1.0842 -2.2475 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1274 -2.2578 -2.1010 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7437 -0.6272 -0.9500 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8444 -1.5421 -0.4860 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2295 -2.2195 0.6390 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3454 -2.1885 1.7025 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1054 -2.3947 2.8563 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1427 -1.3171 3.0440 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8467 -3.7101 2.7507 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6997 -4.4458 3.9289 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2952 -4.5274 1.5954 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0896 -5.6506 1.4643 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3957 -3.7075 0.3036 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3560 -4.1247 -0.5154 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1738 2.6820 0.2073 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1129 1.5871 0.2434 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7755 0.3119 0.5450 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6850 -0.7427 0.5365 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0262 -0.4803 0.2001 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9261 -1.5206 0.1929 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2869 -1.5023 -0.1144 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6406 -2.3110 -1.1608 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9959 -3.5953 -0.8848 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8582 -4.5667 -0.7197 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4508 -5.8205 -0.4417 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0164 -3.7410 0.2382 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3172 -5.0736 0.4007 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4194 -3.1060 1.4761 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3325 -3.7781 1.9790 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1523 -1.6677 1.1263 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3919 -1.0572 0.8611 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3528 0.8125 -0.1015 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4196 1.8523 -0.0861 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6602 3.9420 0.1682 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0463 5.0074 0.1350 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5083 6.2916 0.0941 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1313 9.9182 -0.9691 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0688 10.7619 0.1429 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3034 9.7911 0.8015 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3013 8.1850 0.0364 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1625 6.1591 0.9629 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4286 0.8920 -1.6924 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7717 1.1189 -3.4875 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4930 2.3562 -2.7409 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0976 3.3135 -3.4220 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6009 2.5867 -5.3396 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7905 -0.3750 -3.7010 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2453 0.4692 -2.3913 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6430 -1.1681 -3.0416 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8565 -2.1331 -1.4497 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6116 -0.6690 -0.2103 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2467 -1.8428 0.9303 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4584 -2.4341 3.7549 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1759 -1.6691 2.7830 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1808 -1.0659 4.1225 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8951 -0.3780 2.5050 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9492 -3.5644 2.6296 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0563 -5.3649 3.7748 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2401 -4.7888 1.8097 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6025 -5.6243 0.6161 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3655 -3.9473 -0.1301 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4367 -5.0763 -0.7253 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 0.0830 0.8342 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4213 -1.7603 0.7760 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5337 -0.4501 -0.4595 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5533 -3.9678 -1.8007 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1330 -4.3104 0.0458 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3853 -4.6899 -1.7289 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7897 -6.2537 -1.2610 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8976 -3.1461 -0.0466 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2429 -5.2751 0.0584 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1960 -3.0826 2.2862 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6482 -4.4679 2.6046 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6539 -1.1155 1.9464 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6277 -0.4865 1.6304 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3572 1.0785 -0.3649 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7426 2.8646 -0.3378 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5744 6.3936 0.0902 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 5 7 2 0 7 8 1 0 8 9 2 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 14 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 10 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 46 48 1 0 48 49 1 0 37 50 1 0 50 51 2 0 33 52 1 0 52 53 1 0 53 54 2 0 54 3 1 0 53 7 1 0 21 12 1 0 31 23 1 0 51 34 1 0 48 39 1 0 1 55 1 0 1 56 1 0 1 57 1 0 4 58 1 0 6 59 1 0 12 60 1 6 14 61 1 6 15 62 1 0 15 63 1 0 16 64 1 0 17 65 1 6 18 66 1 0 19 67 1 6 20 68 1 0 21 69 1 1 23 70 1 1 25 71 1 1 26 72 1 0 26 73 1 0 26 74 1 0 27 75 1 6 28 76 1 0 29 77 1 1 30 78 1 0 31 79 1 6 32 80 1 0 35 81 1 0 36 82 1 0 39 83 1 6 41 84 1 6 42 85 1 0 42 86 1 0 43 87 1 0 44 88 1 6 45 89 1 0 46 90 1 1 47 91 1 0 48 92 1 1 49 93 1 0 50 94 1 0 51 95 1 0 54 96 1 0 M END

Standard InCHIKey	COQHRDFLJUXFJY-QEJUJVCISA-N
Standard InCHI	InChI=1S/C34H42O20/c1-11-20(38)24(42)27(45)32(48-11)54-31-26(44)22(40)18(10-36)52-34(31)53-30-23(41)19-15(37)7-14(47-2)8-16(19)50-29(30)12-3-5-13(6-4-12)49-33-28(46)25(43)21(39)17(9-35)51-33/h3-8,11,17-18,20-22,24-28,31-40,42-46H,9-10H2,1-2H3/t11-,17+,18+,20-,21-,22-,24+,25-,26-,27-,28+,31+,32-,33+,34-/m0/s1
SMILES	COC1=CC(O)=C2C(=O)C(O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@@H]3O)=C(C3=CC=C(O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)C=C3)OC2=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	770.23	Volume:	699.994 ? Van der Waals volume.
Dense:	1.1	LogP:	-0.097 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.007 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.91 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	36.0
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:	0.095	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.27	Fsp³:	0.559
MCE-18:	149.774 ? 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:	0.617	Fluc inhibitor:	0.29 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.662 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.558 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.22	Promiscuous compounds:	0.441

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.703	MDCK Permeability:	-5.071
Pgp-inhibitor:	0.0	Pgp-substrate:	0.67
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):	1.0
20% Bioavailability (F20%):	0.944	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.213
Plasma Protein Binding (PPB):	81.858%	Volume Distribution (VD):	-0.133
Fu:	16.482% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.73
HLM stability:	0.015 ? 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):

0.817

Half-life (T1/2):

3.297

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.011
Human Hepatotoxicity (H-HT):	0.837	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.998	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.101	Eye Corrosion:	0.0
Eye Irritation:	0.025	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.994
Hematotoxicity:	0.9	Drug-induced Nephrotoxicity:	0.971
Genotoxicity:	0.836	RPMI-8226 Immunitoxicity:	0.425
A549 Cytotoxicity:	0.992	Hek293 Cytotoxicity:	0.712
BCF:	0.453 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.237 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.927 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.046 ? 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
NPO44395	Cadaba glandulosa	Species	Capparaceae	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 NPC549374 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	20712
0.1-0.2	24336
0.2-0.3	3688
0.3-0.4	632
0.4-0.5	259
0.5-0.6	137
0.6-0.7	53
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8488	Intermediate Similarity	NPC240306
0.8295	Intermediate Similarity	NPC32641
0.8295	Intermediate Similarity	NPC256188
0.8295	Intermediate Similarity	NPC35119
0.7708	Intermediate Similarity	NPC25523
0.7526	Intermediate Similarity	NPC480441
0.747	Intermediate Similarity	NPC289667
0.7292	Intermediate Similarity	NPC14187
0.7283	Intermediate Similarity	NPC64425
0.7053	Intermediate Similarity	NPC142142
0.6966	Remote Similarity	NPC116458
0.6966	Remote Similarity	NPC246943
0.6923	Remote Similarity	NPC251417
0.6804	Remote Similarity	NPC76831
0.6778	Remote Similarity	NPC605784
0.6774	Remote Similarity	NPC163242
0.6774	Remote Similarity	NPC272068
0.6739	Remote Similarity	NPC473682
0.6731	Remote Similarity	NPC295625
0.6705	Remote Similarity	NPC46420
0.6667	Remote Similarity	NPC470715
0.6632	Remote Similarity	NPC470444
0.6591	Remote Similarity	NPC297987
0.6556	Remote Similarity	NPC611303
0.6526	Remote Similarity	NPC155877
0.6517	Remote Similarity	NPC84362
0.6517	Remote Similarity	NPC271692
0.6465	Remote Similarity	NPC220173
0.6458	Remote Similarity	NPC115674
0.6404	Remote Similarity	NPC158674
0.6404	Remote Similarity	NPC136042
0.6354	Remote Similarity	NPC65003
0.6346	Remote Similarity	NPC164704
0.6344	Remote Similarity	NPC170052
0.6344	Remote Similarity	NPC135846
0.6337	Remote Similarity	NPC135358
0.633	Remote Similarity	NPC209550
0.63	Remote Similarity	NPC195257
0.63	Remote Similarity	NPC475382
0.63	Remote Similarity	NPC473071
0.6296	Remote Similarity	NPC470717
0.6292	Remote Similarity	NPC249281
0.6286	Remote Similarity	NPC311850
0.6286	Remote Similarity	NPC277532
0.6264	Remote Similarity	NPC472459
0.6222	Remote Similarity	NPC64305
0.6211	Remote Similarity	NPC239549
0.6182	Remote Similarity	NPC138990
0.6176	Remote Similarity	NPC602448
0.6154	Remote Similarity	NPC473072
0.6147	Remote Similarity	NPC470719
0.6126	Remote Similarity	NPC175429
0.6122	Remote Similarity	NPC186816
0.6105	Remote Similarity	NPC254855
0.6105	Remote Similarity	NPC94610
0.61	Remote Similarity	NPC482026
0.6095	Remote Similarity	NPC48984
0.6091	Remote Similarity	NPC470720
0.6055	Remote Similarity	NPC198199
0.6044	Remote Similarity	NPC95090
0.6044	Remote Similarity	NPC27408
0.6042	Remote Similarity	NPC8856
0.6	Remote Similarity	NPC476215
0.5963	Remote Similarity	NPC68592
0.5957	Remote Similarity	NPC486578
0.5882	Remote Similarity	NPC5319
0.5833	Remote Similarity	NPC276377
0.5806	Remote Similarity	NPC24043
0.5789	Remote Similarity	NPC22832
0.5789	Remote Similarity	NPC21666
0.5784	Remote Similarity	NPC606657
0.5773	Remote Similarity	NPC95866
0.5766	Remote Similarity	NPC470713
0.5752	Remote Similarity	NPC120952
0.5741	Remote Similarity	NPC470712
0.5729	Remote Similarity	NPC136761
0.5729	Remote Similarity	NPC607707
0.5702	Remote Similarity	NPC192539
0.57	Remote Similarity	NPC22062
0.57	Remote Similarity	NPC473634
0.57	Remote Similarity	NPC138811
0.57	Remote Similarity	NPC150164
0.5686	Remote Similarity	NPC12013
0.5686	Remote Similarity	NPC11432
0.5686	Remote Similarity	NPC477613
0.5684	Remote Similarity	NPC285197
0.5684	Remote Similarity	NPC488071
0.5657	Remote Similarity	NPC480466
0.5652	Remote Similarity	NPC262222
0.5648	Remote Similarity	NPC219043
0.5638	Remote Similarity	NPC73511
0.5636	Remote Similarity	NPC470716
0.5636	Remote Similarity	NPC255799
0.5625	Remote Similarity	NPC148710
0.5625	Remote Similarity	NPC243930
0.5625	Remote Similarity	NPC120099
0.5607	Remote Similarity	NPC11468
0.56	Remote Similarity	NPC267680
0.5556	Remote Similarity	NPC480463
0.5545	Remote Similarity	NPC304741
0.5534	Remote Similarity	NPC483414
0.5532	Remote Similarity	NPC277205
0.5532	Remote Similarity	NPC37919
0.55	Remote Similarity	NPC223860
0.5495	Remote Similarity	NPC488083
0.5487	Remote Similarity	NPC298666
0.5481	Remote Similarity	NPC122467
0.5481	Remote Similarity	NPC209296
0.5481	Remote Similarity	NPC72016
0.5474	Remote Similarity	NPC27640
0.5464	Remote Similarity	NPC80188
0.5464	Remote Similarity	NPC609478
0.5463	Remote Similarity	NPC89052
0.5455	Remote Similarity	NPC473644
0.5446	Remote Similarity	NPC470405
0.5426	Remote Similarity	NPC58053
0.5426	Remote Similarity	NPC77672
0.5426	Remote Similarity	NPC133671
0.5426	Remote Similarity	NPC135391
0.5426	Remote Similarity	NPC78263
0.5426	Remote Similarity	NPC250069
0.537	Remote Similarity	NPC244875
0.5368	Remote Similarity	NPC323593
0.5368	Remote Similarity	NPC203500
0.5368	Remote Similarity	NPC189142
0.5368	Remote Similarity	NPC77660
0.5361	Remote Similarity	NPC60735
0.5361	Remote Similarity	NPC219904
0.5361	Remote Similarity	NPC26230
0.5354	Remote Similarity	NPC488072
0.5354	Remote Similarity	NPC267254
0.5354	Remote Similarity	NPC601586
0.534	Remote Similarity	NPC255157
0.534	Remote Similarity	NPC259896
0.5333	Remote Similarity	NPC473327
0.5327	Remote Similarity	NPC292929
0.5327	Remote Similarity	NPC221342
0.5327	Remote Similarity	NPC476470
0.5321	Remote Similarity	NPC121703
0.5321	Remote Similarity	NPC25724
0.5312	Remote Similarity	NPC186807
0.5312	Remote Similarity	NPC488080
0.5312	Remote Similarity	NPC169977
0.5312	Remote Similarity	NPC603655
0.5306	Remote Similarity	NPC224530
0.5263	Remote Similarity	NPC261866
0.5263	Remote Similarity	NPC39360
0.5263	Remote Similarity	NPC29763
0.5263	Remote Similarity	NPC210003
0.5263	Remote Similarity	NPC238376
0.5258	Remote Similarity	NPC42773
0.5258	Remote Similarity	NPC45522
0.5258	Remote Similarity	NPC325555
0.5258	Remote Similarity	NPC226304
0.5258	Remote Similarity	NPC599850
0.5253	Remote Similarity	NPC311830
0.5238	Remote Similarity	NPC470443
0.5217	Remote Similarity	NPC480445
0.521	Remote Similarity	NPC25946
0.5208	Remote Similarity	NPC145038
0.5208	Remote Similarity	NPC56077
0.5208	Remote Similarity	NPC281131
0.5208	Remote Similarity	NPC253662
0.5208	Remote Similarity	NPC179950
0.5208	Remote Similarity	NPC88789
0.5208	Remote Similarity	NPC491374
0.52	Remote Similarity	NPC203050
0.52	Remote Similarity	NPC225434
0.5196	Remote Similarity	NPC139320
0.5185	Remote Similarity	NPC287889
0.5182	Remote Similarity	NPC203145
0.5181	Remote Similarity	NPC262094
0.5158	Remote Similarity	NPC111929
0.5158	Remote Similarity	NPC320283
0.5158	Remote Similarity	NPC41121
0.5146	Remote Similarity	NPC173582
0.5146	Remote Similarity	NPC265885
0.5146	Remote Similarity	NPC181465
0.5146	Remote Similarity	NPC215710
0.5146	Remote Similarity	NPC67105
0.5146	Remote Similarity	NPC473438
0.5146	Remote Similarity	NPC253788
0.514	Remote Similarity	NPC486577
0.5138	Remote Similarity	NPC253685
0.5135	Remote Similarity	NPC189564
0.5104	Remote Similarity	NPC19388
0.5104	Remote Similarity	NPC240431
0.5104	Remote Similarity	NPC55786
0.5104	Remote Similarity	NPC108831
0.5104	Remote Similarity	NPC19709
0.5104	Remote Similarity	NPC182634
0.5102	Remote Similarity	NPC59534
0.5098	Remote Similarity	NPC278419
0.5098	Remote Similarity	NPC179198
0.5096	Remote Similarity	NPC210073
0.5096	Remote Similarity	NPC605592
0.5093	Remote Similarity	NPC89127
0.5089	Remote Similarity	NPC173837
0.5088	Remote Similarity	NPC470718
0.5052	Remote Similarity	NPC265530

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC549374 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5369
0.1-0.2	3701
0.2-0.3	71
0.3-0.4	2
0.4-0.5	3
0.5-0.6	4
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5905	Remote Similarity	NPD7808	Phase 3
0.5882	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD7251	Phase 2
0.5481	Remote Similarity	NPD7054	Phase 4

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