NPASS Compound

Natural Product: NPC14187

Natural Product ID	NPC14187
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Calabricoside A
IUPAC Name	2-(3,4-dihydroxyphenyl)-3-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL447515
PubChem CID	10876384
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 90 95 0 0 0 0 0 0 0 0999 V2000 6.7143 0.4400 3.1255 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0170 1.1061 1.9369 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0608 1.5993 1.0087 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7028 0.4835 0.2751 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8645 -0.7340 0.1705 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4232 -0.6228 0.4667 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0941 0.2616 1.4324 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5888 -0.4524 -0.6451 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7513 -1.5021 -0.8592 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0386 -2.0900 -2.2488 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8661 -2.9820 -2.5547 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1553 -3.5071 -1.3445 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -2.5232 -0.4777 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2930 -1.2687 -0.8230 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7972 -0.3422 0.1102 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4664 0.0624 0.0317 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4747 -0.6908 0.7504 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0640 -1.6774 1.4277 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7994 -0.3576 0.7119 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7572 -1.0625 1.3972 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0979 -0.7015 1.3401 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4596 0.3932 0.5722 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4806 1.0786 -0.1020 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1398 0.7380 -0.0594 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2337 1.4036 -0.7050 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0784 1.1169 -0.6976 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9238 2.0005 -1.4979 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3154 2.8198 -2.4237 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0247 3.7198 -3.1967 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3967 3.7806 -3.0144 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0076 2.9729 -2.0982 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2544 2.0857 -1.3449 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4000 3.0209 -1.8960 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1714 4.6783 -3.7747 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7677 0.8229 0.4578 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8886 0.2811 1.0582 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6443 1.3155 1.9000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1239 1.1371 1.7921 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.5511 -0.3227 1.6727 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6950 -1.0400 0.6616 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5061 -1.7150 -0.3963 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2449 -0.8285 -1.1717 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7910 -0.1472 0.0624 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4834 -0.9677 2.9101 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6035 1.8338 0.6857 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2493 1.1683 3.2289 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3519 -2.1535 2.1557 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3627 -4.1026 -3.2427 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2631 -2.7017 -2.3269 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4188 -1.6989 1.0609 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9529 0.1796 0.8599 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6466 2.6464 0.1867 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2946 -0.5747 3.2994 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8171 0.3204 2.9331 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6493 1.0538 4.0515 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4940 2.0066 2.3792 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8546 2.0815 1.6626 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9868 0.8772 -0.7491 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0642 -1.1799 -0.8356 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1082 -1.6458 0.8714 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9426 -2.3258 -0.0804 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9567 -1.2049 -2.9478 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1518 -2.5048 -3.2797 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7234 -4.3120 -0.8408 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2160 -3.9982 -1.7434 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8336 -1.0570 -1.8030 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8027 -1.2787 1.8913 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7196 1.9539 -0.7246 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7662 2.7942 -2.5910 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5534 4.3617 -3.9257 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7919 1.4979 -0.6141 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0065 2.3435 -2.3458 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9772 4.2618 -4.2178 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6368 -0.5505 1.7335 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3931 2.3546 1.5485 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6396 1.5308 2.6927 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6094 -0.3239 1.3604 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0655 -1.8052 1.1579 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1969 -2.4841 0.0558 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8708 -2.3067 -1.0960 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4413 -1.2607 -2.0456 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5214 -1.0949 3.1471 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8564 1.9914 0.0482 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8088 1.9668 3.5936 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1241 -2.0136 3.1283 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8818 -4.6788 -2.6304 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8910 -2.0299 -2.7511 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7012 -2.1910 1.5393 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1181 -0.7948 0.8443 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1101 3.2655 0.7351 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 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 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 30 34 1 0 22 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 40 43 1 0 39 44 1 0 38 45 1 0 37 46 1 0 20 47 1 0 11 48 1 0 10 49 1 0 5 50 1 0 4 51 1 0 3 52 1 0 7 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 43 36 1 0 24 19 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 1 3 57 1 1 4 58 1 6 5 59 1 6 6 60 1 1 9 61 1 1 10 62 1 6 11 63 1 6 12 64 1 0 12 65 1 0 14 66 1 6 21 67 1 0 23 68 1 0 28 69 1 0 29 70 1 0 32 71 1 0 33 72 1 0 34 73 1 0 36 74 1 1 37 75 1 6 38 76 1 1 39 77 1 6 40 78 1 1 41 79 1 0 41 80 1 0 42 81 1 0 44 82 1 0 45 83 1 0 46 84 1 0 47 85 1 0 48 86 1 0 49 87 1 0 50 88 1 0 51 89 1 0 52 90 1 0 M END

Standard InCHIKey	PIVQUVFXPIBUOI-YTWWQYEOSA-N
Standard InCHI	InChI=1S/C32H38O20/c1-9-19(38)23(42)25(44)30(47-9)52-29-20(39)15(37)8-46-32(29)51-28-22(41)18-14(36)5-11(48-31-26(45)24(43)21(40)17(7-33)50-31)6-16(18)49-27(28)10-2-3-12(34)13(35)4-10/h2-6,9,15,17,19-21,23-26,29-40,42-45H,7-8H2,1H3/t9-,15-,17+,19-,20-,21+,23+,24-,25+,26+,29+,30-,31+,32-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H](CO[C@H]1Oc1c(=O)c2c(cc(cc2oc1c1ccc(c(c1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	742.2	Volume:	665.402 ? Van der Waals volume.
Dense:	1.115	LogP:	0.431 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.188 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.904 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	36.0
TPSA:	328.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	12.0	Rings:	6.0
Heavy Atoms:	20.0

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:	5.344	Fsp³:	0.531
MCE-18:	151.714 ? 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:	0.64	Fluc inhibitor:	0.287 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.86 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.629 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.2	Promiscuous compounds:	0.597

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.82	MDCK Permeability:	-4.948
Pgp-inhibitor:	0.0	Pgp-substrate:	0.753
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%):	0.736	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.013
Plasma Protein Binding (PPB):	70.042%	Volume Distribution (VD):	-0.281
Fu:	28.997% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.186
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:	0.321
HLM stability:	0.013 ? 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):

1.044

Half-life (T1/2):

6.36

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.04
Human Hepatotoxicity (H-HT):	0.717	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.975	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.022	Eye Corrosion:	0.0
Eye Irritation:	0.027	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.17	Drug-induced Nephrotoxicity:	0.923
Genotoxicity:	0.96	RPMI-8226 Immunitoxicity:	0.152
A549 Cytotoxicity:	0.889	Hek293 Cytotoxicity:	0.324
BCF:	0.399 ? 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:	2.911 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.599 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.669 ? 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
NPO30903	Putoria calabrica	n.a.	n.a.	n.a.	n.a.	aerial part	n.a.	PMID[11473436]
NPO30903	Putoria calabrica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11473436]
NPO30903	Putoria calabrica	n.a.	n.a.	n.a.	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

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Non-molecular	1

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.	IC50	=	250.0	nM	PMID[11473436]

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 NPC14187 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	23793
0.1-0.2	21724
0.2-0.3	3450
0.3-0.4	434
0.4-0.5	236
0.5-0.6	156
0.6-0.7	32
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8316	Intermediate Similarity	NPC480441
0.7816	Intermediate Similarity	NPC605784
0.7576	Intermediate Similarity	NPC25523
0.7553	Intermediate Similarity	NPC32641
0.7553	Intermediate Similarity	NPC256188
0.7553	Intermediate Similarity	NPC35119
0.7442	Intermediate Similarity	NPC136042
0.7273	Intermediate Similarity	NPC223860
0.7159	Intermediate Similarity	NPC84362
0.7033	Intermediate Similarity	NPC116458
0.7033	Intermediate Similarity	NPC246943
0.6979	Remote Similarity	NPC240306
0.6809	Remote Similarity	NPC251417
0.6778	Remote Similarity	NPC271692
0.6667	Remote Similarity	NPC297987
0.6667	Remote Similarity	NPC470405
0.6633	Remote Similarity	NPC64425
0.6598	Remote Similarity	NPC155877
0.6596	Remote Similarity	NPC276377
0.6556	Remote Similarity	NPC289667
0.6531	Remote Similarity	NPC115674
0.6436	Remote Similarity	NPC142142
0.6374	Remote Similarity	NPC249281
0.6373	Remote Similarity	NPC473071
0.6364	Remote Similarity	NPC186816
0.6186	Remote Similarity	NPC254855
0.6186	Remote Similarity	NPC94610
0.6186	Remote Similarity	NPC95866
0.6129	Remote Similarity	NPC277205
0.6129	Remote Similarity	NPC37919
0.6129	Remote Similarity	NPC189142
0.6129	Remote Similarity	NPC77660
0.6122	Remote Similarity	NPC8856
0.6105	Remote Similarity	NPC611303
0.61	Remote Similarity	NPC150164
0.6064	Remote Similarity	NPC46420
0.6061	Remote Similarity	NPC480466
0.604	Remote Similarity	NPC255157
0.604	Remote Similarity	NPC259896
0.6019	Remote Similarity	NPC122467
0.6	Remote Similarity	NPC163242
0.6	Remote Similarity	NPC272068
0.6	Remote Similarity	NPC67105
0.5957	Remote Similarity	NPC145038
0.5957	Remote Similarity	NPC56077
0.5957	Remote Similarity	NPC281131
0.5957	Remote Similarity	NPC253662
0.5957	Remote Similarity	NPC179950
0.5957	Remote Similarity	NPC158674
0.5957	Remote Similarity	NPC88789
0.5957	Remote Similarity	NPC491374
0.5943	Remote Similarity	NPC602448
0.5941	Remote Similarity	NPC65003
0.5941	Remote Similarity	NPC210073
0.5938	Remote Similarity	NPC488071
0.5913	Remote Similarity	NPC192539
0.5905	Remote Similarity	NPC76831
0.5851	Remote Similarity	NPC19709
0.5851	Remote Similarity	NPC238376
0.5818	Remote Similarity	NPC164704
0.5784	Remote Similarity	NPC203259
0.5784	Remote Similarity	NPC33054
0.5784	Remote Similarity	NPC176740
0.5784	Remote Similarity	NPC471725
0.5784	Remote Similarity	NPC134532
0.5784	Remote Similarity	NPC156869
0.5784	Remote Similarity	NPC602582
0.5784	Remote Similarity	NPC605592
0.5769	Remote Similarity	NPC470443
0.5729	Remote Similarity	NPC27640
0.5727	Remote Similarity	NPC219043
0.5727	Remote Similarity	NPC292019
0.5727	Remote Similarity	NPC202908
0.5714	Remote Similarity	NPC72016
0.569	Remote Similarity	NPC209550
0.5686	Remote Similarity	NPC471748
0.5684	Remote Similarity	NPC127546
0.5684	Remote Similarity	NPC57625
0.5684	Remote Similarity	NPC173637
0.5684	Remote Similarity	NPC317489
0.5684	Remote Similarity	NPC223424
0.5684	Remote Similarity	NPC600591
0.5676	Remote Similarity	NPC470715
0.567	Remote Similarity	NPC42773
0.567	Remote Similarity	NPC45522
0.567	Remote Similarity	NPC599850
0.5607	Remote Similarity	NPC195257
0.5607	Remote Similarity	NPC473073
0.5607	Remote Similarity	NPC220173
0.56	Remote Similarity	NPC170052
0.56	Remote Similarity	NPC476215
0.56	Remote Similarity	NPC135846
0.5588	Remote Similarity	NPC29958
0.5577	Remote Similarity	NPC470444
0.5566	Remote Similarity	NPC606657
0.5556	Remote Similarity	NPC138990
0.5536	Remote Similarity	NPC303694
0.5524	Remote Similarity	NPC488073
0.5524	Remote Similarity	NPC126784
0.5524	Remote Similarity	NPC241423
0.5521	Remote Similarity	NPC39360
0.5521	Remote Similarity	NPC29763
0.5521	Remote Similarity	NPC210003
0.5517	Remote Similarity	NPC470719
0.5517	Remote Similarity	NPC470717
0.551	Remote Similarity	NPC59534
0.5508	Remote Similarity	NPC175429
0.5505	Remote Similarity	NPC253685
0.549	Remote Similarity	NPC473682
0.5481	Remote Similarity	NPC304741
0.5478	Remote Similarity	NPC295625
0.5472	Remote Similarity	NPC12013
0.5472	Remote Similarity	NPC483414
0.5472	Remote Similarity	NPC11432
0.5472	Remote Similarity	NPC477613
0.5464	Remote Similarity	NPC323593
0.5464	Remote Similarity	NPC203500
0.5463	Remote Similarity	NPC89127
0.5446	Remote Similarity	NPC48984
0.5431	Remote Similarity	NPC298666
0.5413	Remote Similarity	NPC292929
0.5413	Remote Similarity	NPC221342
0.5413	Remote Similarity	NPC476470
0.5408	Remote Similarity	NPC305811
0.5392	Remote Similarity	NPC265115
0.5385	Remote Similarity	NPC44931
0.5385	Remote Similarity	NPC67326
0.5385	Remote Similarity	NPC275454
0.5385	Remote Similarity	NPC227508
0.537	Remote Similarity	NPC486577
0.5364	Remote Similarity	NPC135358
0.5361	Remote Similarity	NPC77672
0.5361	Remote Similarity	NPC133671
0.5361	Remote Similarity	NPC135391
0.5361	Remote Similarity	NPC78263
0.5361	Remote Similarity	NPC250069
0.5357	Remote Similarity	NPC473072
0.5357	Remote Similarity	NPC488075
0.5351	Remote Similarity	NPC311850
0.5351	Remote Similarity	NPC277532
0.534	Remote Similarity	NPC480463
0.5339	Remote Similarity	NPC480444
0.5339	Remote Similarity	NPC470720
0.5321	Remote Similarity	NPC475382
0.5312	Remote Similarity	NPC67037
0.5312	Remote Similarity	NPC255615
0.5306	Remote Similarity	NPC64305
0.5306	Remote Similarity	NPC95090
0.5306	Remote Similarity	NPC27408
0.5304	Remote Similarity	NPC470716
0.53	Remote Similarity	NPC285197
0.5299	Remote Similarity	NPC198199
0.5294	Remote Similarity	NPC190003
0.5268	Remote Similarity	NPC203145
0.5258	Remote Similarity	NPC473043
0.5258	Remote Similarity	NPC331652
0.5253	Remote Similarity	NPC24043
0.5248	Remote Similarity	NPC22832
0.5248	Remote Similarity	NPC601144
0.5238	Remote Similarity	NPC173582
0.5238	Remote Similarity	NPC265885
0.5238	Remote Similarity	NPC181465
0.5238	Remote Similarity	NPC215710
0.5238	Remote Similarity	NPC473438
0.5238	Remote Similarity	NPC253788
0.5221	Remote Similarity	NPC189564
0.5214	Remote Similarity	NPC68592
0.5204	Remote Similarity	NPC19388
0.5204	Remote Similarity	NPC261866
0.5204	Remote Similarity	NPC240431
0.5204	Remote Similarity	NPC55786
0.5204	Remote Similarity	NPC108831
0.5204	Remote Similarity	NPC182634
0.52	Remote Similarity	NPC472459
0.5196	Remote Similarity	NPC311830
0.5189	Remote Similarity	NPC22062
0.5189	Remote Similarity	NPC473634
0.5189	Remote Similarity	NPC138811
0.5185	Remote Similarity	NPC483415
0.5167	Remote Similarity	NPC120952
0.5149	Remote Similarity	NPC60735
0.5149	Remote Similarity	NPC26230
0.5143	Remote Similarity	NPC139320
0.5138	Remote Similarity	NPC483416
0.5138	Remote Similarity	NPC209296
0.5133	Remote Similarity	NPC89052
0.5126	Remote Similarity	NPC488740
0.5102	Remote Similarity	NPC111929
0.5102	Remote Similarity	NPC320283
0.5102	Remote Similarity	NPC41121
0.5098	Remote Similarity	NPC243930
0.5098	Remote Similarity	NPC120099
0.5098	Remote Similarity	NPC21666
0.5098	Remote Similarity	NPC486578
0.5096	Remote Similarity	NPC116864
0.5096	Remote Similarity	NPC244776
0.5094	Remote Similarity	NPC39834
0.5093	Remote Similarity	NPC488074
0.5052	Remote Similarity	NPC276222

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC14187 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5719
0.1-0.2	3360
0.2-0.3	62
0.3-0.4	2
0.4-0.5	3
0.5-0.6	3
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
0.6869	Remote Similarity	NPD7251	Phase 2
0.5833	Remote Similarity	NPD7808	Phase 3
0.5784	Remote Similarity	NPD6797	Phase 2
0.5138	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