NPASS Compound

Natural Product: NPC585983

Natural Product ID	NPC585983
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-7-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-7-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]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 94 99 0 0 0 0 0 0 0 0999 V2000 -7.4886 3.2896 -2.9780 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9174 2.1409 -2.1618 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6717 1.7666 -2.5909 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1315 0.8844 -1.6133 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5095 1.3924 -0.4040 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5463 1.7603 0.4917 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6834 0.6501 1.0112 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0054 0.0409 0.0318 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2353 -1.0854 0.3799 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3001 -0.6387 1.3451 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0020 -0.3183 0.9753 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0436 -1.1710 1.0865 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9888 -2.5342 1.6200 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0824 -3.3750 1.3856 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1264 -4.6478 1.9100 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2016 -5.4942 1.6876 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0905 -5.1244 2.6810 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1344 -6.4189 3.2146 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0004 -4.3123 2.9267 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0199 -4.8192 3.7018 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0107 -3.0381 2.3838 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2366 -0.7210 0.6694 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4644 0.4566 0.1771 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7518 0.8347 -0.2301 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0394 2.0695 -0.7535 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2761 2.4952 -1.1657 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4602 1.7725 -1.1510 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3474 2.2608 -0.1512 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2334 1.1781 0.0668 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0266 1.3202 1.3223 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1115 0.9929 -1.1625 C 0 0 2 0 0 0 0 0 0 0 0 0 10.4089 1.3456 -0.7953 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6546 1.9321 -2.2682 C 0 0 2 0 0 0 0 0 0 0 0 0 9.2012 3.1854 -2.0411 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1750 1.9432 -2.4685 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7561 0.9130 -3.3306 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9735 2.9635 -0.8712 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6985 2.6185 -0.4798 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6454 3.5184 -0.6027 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4486 1.3728 0.0406 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1900 0.9673 0.4519 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7227 1.7973 0.3258 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1992 -2.0847 0.8915 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7923 -3.3804 0.9941 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7439 -1.5344 2.2155 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5547 -2.4631 2.8485 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4684 -0.2304 1.9393 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7359 0.3744 3.1519 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8171 -0.4692 -1.7812 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0026 -1.2373 -2.6078 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1464 -0.2932 -2.4917 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9689 -1.3593 -2.0631 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8355 0.9717 -2.1143 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4923 0.8641 -0.8686 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7588 4.1335 -2.8597 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5589 3.0574 -4.0381 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4254 3.6017 -2.4916 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8451 2.5411 -1.1055 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0553 0.8405 -1.7509 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9276 2.5527 -0.0215 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0320 2.3334 1.3258 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9310 1.1680 1.6929 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7259 -1.3530 -0.5801 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9237 -3.0578 0.7909 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7966 -5.2692 0.8932 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6081 -6.6225 4.0883 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0461 -4.7477 4.7147 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8642 -2.4412 2.6183 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5159 0.1112 -0.1151 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2597 0.7122 -0.8890 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5962 0.2746 0.1470 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5142 0.8756 2.2084 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9695 0.7185 1.2004 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3337 2.3621 1.5515 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0426 -0.0397 -1.5719 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3554 2.1343 -0.2148 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1334 1.5565 -3.2184 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0880 3.4944 -1.0983 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8785 2.9387 -2.8764 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3006 0.9302 -4.1765 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1702 3.9425 -1.2794 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4926 4.0511 -1.4488 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1547 -2.0653 0.2233 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7947 -3.7589 1.8901 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8726 -1.3325 2.8568 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0968 -3.0894 3.4305 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4300 -0.4947 1.4730 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2014 1.1922 3.3183 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0086 -0.9615 -0.8128 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3445 -2.1698 -2.6808 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0615 -0.4265 -3.5887 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7293 -2.1992 -2.5326 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6774 1.1399 -2.8494 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2068 0.0442 -0.3919 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 15 17 2 0 17 18 1 0 17 19 1 0 19 20 1 0 19 21 2 0 12 22 1 0 22 23 1 0 23 24 2 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 31 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 25 37 2 0 37 38 1 0 38 39 1 0 38 40 2 0 40 41 1 0 41 42 2 0 9 43 1 0 43 44 1 0 43 45 1 0 45 46 1 0 45 47 1 0 47 48 1 0 4 49 1 0 49 50 1 0 49 51 1 0 51 52 1 0 51 53 1 0 53 54 1 0 53 2 1 0 47 7 1 0 41 11 1 0 21 13 1 0 40 23 1 0 35 27 1 0 1 55 1 0 1 56 1 0 1 57 1 0 2 58 1 1 4 59 1 1 6 60 1 0 6 61 1 0 7 62 1 1 9 63 1 6 14 64 1 0 16 65 1 0 18 66 1 0 20 67 1 0 21 68 1 0 24 69 1 0 27 70 1 1 29 71 1 1 30 72 1 0 30 73 1 0 30 74 1 0 31 75 1 6 32 76 1 0 33 77 1 6 34 78 1 0 35 79 1 6 36 80 1 0 37 81 1 0 39 82 1 0 43 83 1 6 44 84 1 0 45 85 1 1 46 86 1 0 47 87 1 6 48 88 1 0 49 89 1 1 50 90 1 0 51 91 1 6 52 92 1 0 53 93 1 6 54 94 1 0 M END

Standard InCHIKey	PUGCFQSSZSFPTE-ZNQWRHSHSA-N
Standard InCHI	InChI=1S/C33H40O21/c1-8-18(37)23(42)26(45)31(49-8)48-7-16-21(40)25(44)28(47)33(53-16)54-30-22(41)17-12(34)5-11(51-32-27(46)24(43)19(38)9(2)50-32)6-15(17)52-29(30)10-3-13(35)20(39)14(36)4-10/h3-6,8-9,16,18-19,21,23-28,31-40,42-47H,7H2,1-2H3/t8-,9+,16-,18-,19-,21-,23-,24-,25+,26+,27+,28-,31+,32-,33-/m0/s1
SMILES	C[C@@H]1O[C@@H](OC[C@@H]2O[C@@H](OC3=C(C4=CC(O)=C(O)C(O)=C4)OC4=CC(O[C@@H]5O[C@H](C)[C@H](O)[C@H](O)[C@H]5O)=CC(O)=C4C3=O)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	772.21	Volume:	691.488 ? Van der Waals volume.
Dense:	1.117	LogP:	0.607 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.193 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.993 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	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:	0.099	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.481	Fsp³:	0.545
MCE-18:	157.882 ? 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:	1
Colloidal aggregators:	0.653	Fluc inhibitor:	0.197 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.805 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.636 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.198	Promiscuous compounds:	0.617

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.689	MDCK Permeability:	-4.953
Pgp-inhibitor:	0.0	Pgp-substrate:	0.989
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):	0.919
20% Bioavailability (F20%):	0.644	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.009
Plasma Protein Binding (PPB):	73.062%	Volume Distribution (VD):	-0.152
Fu:	25.565% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.091
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:	0.019
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.051 ? 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):

0.776

Half-life (T1/2):

7.255

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.36
Human Hepatotoxicity (H-HT):	0.328	Drug-induced Liver Injury (DILI):	0.969
AMES Toxicity:	0.937	Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.021	Skin Sensitization:	1.0
Carcinogencity:	0.005	Eye Corrosion:	0.0
Eye Irritation:	0.033	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.023	Drug-induced Nephrotoxicity:	0.402
Genotoxicity:	0.858	RPMI-8226 Immunitoxicity:	0.044
A549 Cytotoxicity:	0.974	Hek293 Cytotoxicity:	0.206
BCF:	0.3 ? 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:	2.912 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.67 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.733 ? 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
NPO12373	Vinca minor	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 29131648]
NPO30789	Eustoma grandiflorum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[559754]
NPO12373	Vinca minor	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30789	Eustoma grandiflorum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12373	Vinca minor	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12373	Vinca minor	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12373	Vinca minor	Species	Apocynaceae	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 NPC585983 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	22774
0.1-0.2	23826
0.2-0.3	2428
0.3-0.4	393
0.4-0.5	267
0.5-0.6	98
0.6-0.7	53
0.7-0.8	3
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8434	Intermediate Similarity	NPC186816
0.8077	Intermediate Similarity	NPC158674
0.7976	Intermediate Similarity	NPC39834
0.7976	Intermediate Similarity	NPC227508
0.7356	Intermediate Similarity	NPC67105
0.7273	Intermediate Similarity	NPC210073
0.7108	Intermediate Similarity	NPC271692
0.7079	Intermediate Similarity	NPC203259
0.7079	Intermediate Similarity	NPC33054
0.7079	Intermediate Similarity	NPC176740
0.7079	Intermediate Similarity	NPC471725
0.7079	Intermediate Similarity	NPC134532
0.7079	Intermediate Similarity	NPC602582
0.7033	Intermediate Similarity	NPC470443
0.701	Intermediate Similarity	NPC480441
0.6966	Remote Similarity	NPC275454
0.6867	Remote Similarity	NPC249281
0.6809	Remote Similarity	NPC473073
0.6782	Remote Similarity	NPC605784
0.6778	Remote Similarity	NPC173582
0.6778	Remote Similarity	NPC44931
0.6778	Remote Similarity	NPC265885
0.6778	Remote Similarity	NPC181465
0.6778	Remote Similarity	NPC215710
0.6778	Remote Similarity	NPC473438
0.6778	Remote Similarity	NPC253788
0.6739	Remote Similarity	NPC126784
0.6739	Remote Similarity	NPC241423
0.6706	Remote Similarity	NPC46420
0.6705	Remote Similarity	NPC276377
0.6703	Remote Similarity	NPC22062
0.6703	Remote Similarity	NPC65563
0.6703	Remote Similarity	NPC473634
0.6703	Remote Similarity	NPC470949
0.6703	Remote Similarity	NPC138811
0.6667	Remote Similarity	NPC25523
0.6596	Remote Similarity	NPC209296
0.6552	Remote Similarity	NPC611303
0.6548	Remote Similarity	NPC473043
0.6548	Remote Similarity	NPC135599
0.6548	Remote Similarity	NPC73855
0.6548	Remote Similarity	NPC113968
0.6548	Remote Similarity	NPC328940
0.6548	Remote Similarity	NPC277174
0.6548	Remote Similarity	NPC606877
0.6526	Remote Similarity	NPC142142
0.6421	Remote Similarity	NPC473327
0.6404	Remote Similarity	NPC116458
0.6404	Remote Similarity	NPC246943
0.6354	Remote Similarity	NPC486577
0.6344	Remote Similarity	NPC150164
0.6322	Remote Similarity	NPC349108
0.6289	Remote Similarity	NPC476472
0.6289	Remote Similarity	NPC294815
0.6289	Remote Similarity	NPC16194
0.6277	Remote Similarity	NPC473571
0.6277	Remote Similarity	NPC110941
0.6263	Remote Similarity	NPC14187
0.6207	Remote Similarity	NPC136042
0.6196	Remote Similarity	NPC251417
0.617	Remote Similarity	NPC156869
0.6154	Remote Similarity	NPC355481
0.6092	Remote Similarity	NPC238376
0.6082	Remote Similarity	NPC32641
0.6082	Remote Similarity	NPC256188
0.6082	Remote Similarity	NPC72016
0.6064	Remote Similarity	NPC67326
0.6	Remote Similarity	NPC303913
0.5918	Remote Similarity	NPC35119
0.5918	Remote Similarity	NPC606657
0.5909	Remote Similarity	NPC289667
0.5909	Remote Similarity	NPC19709
0.5876	Remote Similarity	NPC488073
0.5851	Remote Similarity	NPC480463
0.5843	Remote Similarity	NPC297987
0.5816	Remote Similarity	NPC65711
0.5789	Remote Similarity	NPC471079
0.5778	Remote Similarity	NPC84362
0.5778	Remote Similarity	NPC27640
0.5769	Remote Similarity	NPC292019
0.5769	Remote Similarity	NPC202908
0.5758	Remote Similarity	NPC122467
0.5745	Remote Similarity	NPC116864
0.5745	Remote Similarity	NPC244776
0.573	Remote Similarity	NPC127546
0.573	Remote Similarity	NPC57625
0.573	Remote Similarity	NPC173637
0.573	Remote Similarity	NPC317489
0.573	Remote Similarity	NPC223424
0.573	Remote Similarity	NPC600591
0.5728	Remote Similarity	NPC121703
0.5714	Remote Similarity	NPC488074
0.567	Remote Similarity	NPC293626
0.5644	Remote Similarity	NPC89127
0.5625	Remote Similarity	NPC187379
0.5612	Remote Similarity	NPC204693
0.56	Remote Similarity	NPC473623
0.5588	Remote Similarity	NPC101636
0.5567	Remote Similarity	NPC267680
0.5556	Remote Similarity	NPC19388
0.5556	Remote Similarity	NPC240431
0.5556	Remote Similarity	NPC55786
0.5556	Remote Similarity	NPC240306
0.5556	Remote Similarity	NPC108831
0.5556	Remote Similarity	NPC182634
0.5545	Remote Similarity	NPC488089
0.5543	Remote Similarity	NPC59534
0.5534	Remote Similarity	NPC470446
0.5524	Remote Similarity	NPC189564
0.5514	Remote Similarity	NPC277532
0.55	Remote Similarity	NPC12013
0.55	Remote Similarity	NPC11432
0.55	Remote Similarity	NPC477613
0.5495	Remote Similarity	NPC265530
0.5446	Remote Similarity	NPC229409
0.5444	Remote Similarity	NPC111929
0.5444	Remote Similarity	NPC320283
0.5444	Remote Similarity	NPC331652
0.5444	Remote Similarity	NPC41121
0.5437	Remote Similarity	NPC470445
0.5435	Remote Similarity	NPC305811
0.5429	Remote Similarity	NPC203145
0.5429	Remote Similarity	NPC11468
0.5417	Remote Similarity	NPC265115
0.5385	Remote Similarity	NPC135358
0.531	Remote Similarity	NPC209550
0.5306	Remote Similarity	NPC609888
0.5294	Remote Similarity	NPC37668
0.5288	Remote Similarity	NPC221342
0.5288	Remote Similarity	NPC476470
0.5278	Remote Similarity	NPC303694
0.5248	Remote Similarity	NPC64425
0.5248	Remote Similarity	NPC475366
0.5238	Remote Similarity	NPC602448
0.5222	Remote Similarity	NPC34531
0.52	Remote Similarity	NPC479405
0.52	Remote Similarity	NPC605592
0.5196	Remote Similarity	NPC483414
0.5196	Remote Similarity	NPC479403
0.5196	Remote Similarity	NPC483415
0.5192	Remote Similarity	NPC471669
0.5175	Remote Similarity	NPC241781
0.5161	Remote Similarity	NPC277205
0.5161	Remote Similarity	NPC37919
0.5158	Remote Similarity	NPC182121
0.5158	Remote Similarity	NPC219904
0.5155	Remote Similarity	NPC190003
0.5152	Remote Similarity	NPC480466
0.5149	Remote Similarity	NPC479404
0.5146	Remote Similarity	NPC483416
0.5146	Remote Similarity	NPC270448
0.5143	Remote Similarity	NPC298171
0.5143	Remote Similarity	NPC470449
0.514	Remote Similarity	NPC89052
0.5138	Remote Similarity	NPC473644
0.5133	Remote Similarity	NPC156785
0.5104	Remote Similarity	NPC181616
0.5098	Remote Similarity	NPC46202
0.5098	Remote Similarity	NPC153755
0.5098	Remote Similarity	NPC64051
0.5091	Remote Similarity	NPC311850
0.5052	Remote Similarity	NPC223747
0.5052	Remote Similarity	NPC99957
0.5048	Remote Similarity	NPC470447
0.5046	Remote Similarity	NPC173837
0.5044	Remote Similarity	NPC198199

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC585983 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5642
0.1-0.2	3465
0.2-0.3	34
0.3-0.4	3
0.4-0.5	1
0.5-0.6	1
0.6-0.7	1
0.7-0.8	3
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
0.7955	Intermediate Similarity	NPD7251	Phase 2
0.7234	Intermediate Similarity	NPD7808	Phase 3
0.7079	Intermediate Similarity	NPD6797	Phase 2
0.6596	Remote Similarity	NPD7054	Phase 4
0.514	Remote Similarity	NPD7472	Pre-clinical

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