NPASS Compound

Structure

CID188815 OpenBabel06191715572D 53 58 0 0 1 0 0 0 0 0999 V2000 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 10 1 0 0 0 0 2 21 2 0 0 0 0 3 11 2 0 0 0 0 3 21 1 0 0 0 0 4 12 1 0 0 0 0 4 22 2 0 0 0 0 5 13 2 0 0 0 0 5 22 1 0 0 0 0 6 16 2 0 0 0 0 6 21 1 0 0 0 0 7 17 2 0 0 0 0 7 22 1 0 0 0 0 8 14 1 0 0 0 0 8 23 2 0 0 0 0 9 15 2 0 0 0 0 9 23 1 0 0 0 0 10 24 2 0 0 0 0 11 24 1 0 0 0 0 12 25 2 0 0 0 0 13 25 1 0 0 0 0 14 26 2 0 0 0 0 15 26 1 0 0 0 0 16 30 1 0 0 0 0 17 31 1 0 0 0 0 18 27 2 0 0 0 0 18 28 1 0 0 0 0 19 27 1 0 0 0 0 19 29 2 0 0 0 0 20 1 1 6 0 0 0 20 33 1 0 0 0 0 20 49 1 0 0 0 0 23 36 1 0 0 0 0 24 40 1 0 0 0 0 25 41 1 0 0 0 0 26 42 1 0 0 0 0 27 50 1 0 0 0 0 28 32 2 0 0 0 0 28 43 1 0 0 0 0 29 32 1 0 0 0 0 29 51 1 0 0 0 0 30 44 2 0 0 0 0 30 52 1 0 0 0 0 31 45 2 0 0 0 0 31 53 1 0 0 0 0 32 34 1 0 0 0 0 33 37 1 0 0 0 0 33 46 1 1 0 0 0 34 35 1 0 0 0 0 34 47 2 0 0 0 0 35 36 2 0 0 0 0 35 48 1 0 0 0 0 36 51 1 0 0 0 0 37 38 1 0 0 0 0 37 52 1 6 0 0 0 38 39 1 0 0 0 0 38 53 1 6 0 0 0 39 49 1 0 0 0 0 39 50 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	724.18
Volume:	707.368
LogP:	5.102
LogD:	2.751
LogS:	-3.948
# Rotatable Bonds:	11
TPSA:	222.65
# H-Bond Aceptor:	14
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.089
Synthetic Accessibility Score:	4.508
Fsp3:	0.154
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.798
MDCK Permeability:	2.6370320483692922e-05
Pgp-inhibitor:	0.052
Pgp-substrate:	0.049
Human Intestinal Absorption (HIA):	0.163
20% Bioavailability (F20%):	0.899
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	102.85686492919922%
Volume Distribution (VD):	0.486
Pgp-substrate:	0.839091956615448%

ADMET: Metabolism

CYP1A2-inhibitor:	0.576
CYP1A2-substrate:	0.021
CYP2C19-inhibitor:	0.824
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.503
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.874
CYP2D6-substrate:	0.302
CYP3A4-inhibitor:	0.498
CYP3A4-substrate:	0.101

ADMET: Excretion

Clearance (CL):	5.708
Half-life (T1/2):	0.86

ADMET: Toxicity

hERG Blockers:	0.29
Human Hepatotoxicity (H-HT):	0.906
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.664
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.128
Skin Sensitization:	0.947
Carcinogencity:	0.114
Eye Corrosion:	0.003
Eye Irritation:	0.176
Respiratory Toxicity:	0.025

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC188815

Natural Product ID:	NPC188815
*Common Name:**	Kaempferol 7-O-(2,3-Di-E-P-Coumaroyl-Alpha-L-Rhamnoside)
IUPAC Name:	[(2S,3R,4R,5S,6S)-2-[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-5-hydroxy-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-6-methyloxan-4-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	MCRKSHUHZRIUDW-UHXFTNJJSA-N
Standard InCHI:	InChI=1S/C39H32O14/c1-20-33(46)37(52-30(44)16-6-21-2-10-24(40)11-3-21)38(53-31(45)17-7-22-4-12-25(41)13-5-22)39(49-20)50-27-18-28(43)32-29(19-27)51-36(35(48)34(32)47)23-8-14-26(42)15-9-23/h2-20,33,37-43,46,48H,1H3/b16-6+,17-7+/t20-,33-,37+,38+,39-/m0/s1
SMILES:	Oc1ccc(cc1)/C=C/C(=O)O[C@H]1[C@H](Oc2cc(O)c3c(c2)oc(c(c3=O)O)c2ccc(cc2)O)O[C@H]([C@@H]([C@H]1OC(=O)/C=C/c1ccc(cc1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451278
PubChem CID:	11607311
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

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843584]
NPO27252	Iochroma australe	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota	n.a.	antarctic	n.a.	PMID[15270575]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497934]
NPO30570	Tetrapanax papyriferus	Species	Araliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16378372]
NPO30570	Tetrapanax papyriferus	Species	Araliaceae	Eukaryota	n.a.	flower	n.a.	PMID[16378372]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407007]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30570	Tetrapanax papyriferus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2039	Callerya cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30570	Tetrapanax papyriferus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19823	Vicia benghalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25952	Lastrea thelypteris	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26980	Halocarpus biformis	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26109	Pilocarpus spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25926	Tephrosia pumila	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25873	Thaminophyllum multiflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24378	Osmanthus heterophyllus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26727	Eremocarpus setiger	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26625	Stichopus chloronotus	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26078	Mussaenda parviflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26678	Calea pilosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26408	Melanophryniscus moreirae	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26352	Heuchera cylindrica	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26135	Walsura tubulata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11845	Petrorhagia dubia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3346	Piper sanctum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26535	Balanus glandula	Species	Balanidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25849	Streptomyces lomondensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18292	Guarea trichilioides	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26289	Lecidella chodati	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25793	Gremmeniella abietina	Species	Helotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26453	Prunus lusitanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26952	Cineraria geifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26053	Pluchea suaveolens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26377	Amelanchier vulgaris	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26563	Alectoria japonica	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27377	Diaporthe helianthi	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26186	Stereocaulon leprocauloides	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26026	Vitis silvestris	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26884	Helichrysum davenportii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13781	Eremostachys moluccelloides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25741	Aster ageratoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26430	Aplysina laevis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7214	Bufotes viridis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26754	Stevia connata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27252	Iochroma australe	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26244	Panax papyrifer	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2344	Carlina acanthifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2039	Callerya cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO137	Nepeta multifida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26213	Tephrosia vogelii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26903	Plectranthus purpuratus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25997	Senecio rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14466	Penicillium olsonii	Species	Aspergillaceae	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	NP ID	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	LC50	=	400000.0	nM	PMID[470465]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC188815 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	1682
0.2-0.3	4085
0.3-0.4	9061
0.4-0.5	9258
0.5-0.6	4650
0.6-0.7	5730
0.7-0.8	5198
0.8-0.85	1596
0.85-0.9	537
0.9-0.95	420
0.95-1	76

Similarity Score	Similarity Level	Natural Product ID
0.9938	High Similarity	NPC11847
0.9938	High Similarity	NPC217822
0.9938	High Similarity	NPC101399
0.9938	High Similarity	NPC221288
0.9875	High Similarity	NPC280642
0.9875	High Similarity	NPC96605
0.9875	High Similarity	NPC469344
0.9875	High Similarity	NPC218161
0.9811	High Similarity	NPC473278
0.9811	High Similarity	NPC260504
0.9811	High Similarity	NPC89809
0.9755	High Similarity	NPC231787
0.9752	High Similarity	NPC92815
0.9748	High Similarity	NPC139060
0.9691	High Similarity	NPC474522
0.9686	High Similarity	NPC80068
0.963	High Similarity	NPC470712
0.963	High Similarity	NPC164704
0.9625	High Similarity	NPC85751
0.9625	High Similarity	NPC205824
0.9625	High Similarity	NPC129264
0.9625	High Similarity	NPC19240
0.9571	High Similarity	NPC470715
0.9571	High Similarity	NPC470716
0.9571	High Similarity	NPC470714
0.956	High Similarity	NPC477628
0.956	High Similarity	NPC472994
0.956	High Similarity	NPC270675
0.956	High Similarity	NPC477629
0.956	High Similarity	NPC195685
0.956	High Similarity	NPC210961
0.9509	High Similarity	NPC76047
0.9444	High Similarity	NPC64425
0.9437	High Similarity	NPC216496
0.9437	High Similarity	NPC159579
0.9437	High Similarity	NPC101636
0.9437	High Similarity	NPC259957
0.9437	High Similarity	NPC224530
0.9437	High Similarity	NPC48093
0.9437	High Similarity	NPC85707
0.9437	High Similarity	NPC129217
0.9437	High Similarity	NPC470125
0.9408	High Similarity	NPC474093
0.9408	High Similarity	NPC104910
0.9401	High Similarity	NPC471030
0.939	High Similarity	NPC175429
0.939	High Similarity	NPC277532
0.939	High Similarity	NPC138990
0.939	High Similarity	NPC209550
0.9383	High Similarity	NPC135358
0.9383	High Similarity	NPC287889
0.9379	High Similarity	NPC27942
0.9379	High Similarity	NPC240306
0.9379	High Similarity	NPC298171
0.9379	High Similarity	NPC472876
0.9375	High Similarity	NPC187379
0.9371	High Similarity	NPC108831
0.9371	High Similarity	NPC182634
0.9353	High Similarity	NPC475179
0.9353	High Similarity	NPC97817
0.9353	High Similarity	NPC30011
0.9353	High Similarity	NPC72554
0.9349	High Similarity	NPC75574
0.9341	High Similarity	NPC477895
0.9325	High Similarity	NPC68592
0.9325	High Similarity	NPC256188
0.9325	High Similarity	NPC298666
0.9325	High Similarity	NPC12013
0.9325	High Similarity	NPC11432
0.9325	High Similarity	NPC189564
0.9325	High Similarity	NPC32641
0.9325	High Similarity	NPC203145
0.9325	High Similarity	NPC221342
0.9325	High Similarity	NPC186816
0.9325	High Similarity	NPC142142
0.9325	High Similarity	NPC477613
0.9325	High Similarity	NPC262222
0.9325	High Similarity	NPC476470
0.9321	High Similarity	NPC121703
0.9317	High Similarity	NPC249281
0.9317	High Similarity	NPC265885
0.9317	High Similarity	NPC246943
0.9317	High Similarity	NPC476215
0.9317	High Similarity	NPC473438
0.9317	High Similarity	NPC139320
0.9317	High Similarity	NPC282169
0.9317	High Similarity	NPC253788
0.9317	High Similarity	NPC215710
0.9317	High Similarity	NPC181465
0.9317	High Similarity	NPC163242
0.9317	High Similarity	NPC116458
0.9317	High Similarity	NPC276377
0.9317	High Similarity	NPC173582
0.9313	High Similarity	NPC22062
0.9313	High Similarity	NPC111929
0.9313	High Similarity	NPC104677
0.9313	High Similarity	NPC320283
0.9313	High Similarity	NPC472459
0.9313	High Similarity	NPC473634
0.9313	High Similarity	NPC138811
0.9313	High Similarity	NPC41121
0.9308	High Similarity	NPC323593
0.9308	High Similarity	NPC203500
0.9308	High Similarity	NPC307938
0.929	High Similarity	NPC297503
0.929	High Similarity	NPC135831
0.929	High Similarity	NPC162394
0.929	High Similarity	NPC156785
0.929	High Similarity	NPC97119
0.929	High Similarity	NPC241781
0.9264	High Similarity	NPC289667
0.9264	High Similarity	NPC292929
0.9264	High Similarity	NPC76831
0.9264	High Similarity	NPC72016
0.9259	High Similarity	NPC475382
0.9259	High Similarity	NPC244875
0.9255	High Similarity	NPC471079
0.9255	High Similarity	NPC473623
0.9255	High Similarity	NPC304741
0.9255	High Similarity	NPC136761
0.9255	High Similarity	NPC470405
0.925	High Similarity	NPC78263
0.925	High Similarity	NPC54802
0.925	High Similarity	NPC77672
0.925	High Similarity	NPC65003
0.925	High Similarity	NPC135391
0.925	High Similarity	NPC43638
0.925	High Similarity	NPC473512
0.925	High Similarity	NPC197304
0.925	High Similarity	NPC129827
0.925	High Similarity	NPC133671
0.925	High Similarity	NPC44931
0.9245	High Similarity	NPC27408
0.9245	High Similarity	NPC95090
0.9235	High Similarity	NPC460984
0.9235	High Similarity	NPC223860
0.9235	High Similarity	NPC470717
0.9235	High Similarity	NPC25946
0.9235	High Similarity	NPC470720
0.9235	High Similarity	NPC21359
0.9235	High Similarity	NPC249560
0.9235	High Similarity	NPC470713
0.9235	High Similarity	NPC275977
0.9226	High Similarity	NPC35167
0.9226	High Similarity	NPC217520
0.9226	High Similarity	NPC139571
0.9222	High Similarity	NPC34267
0.9222	High Similarity	NPC223426
0.9222	High Similarity	NPC81042
0.9222	High Similarity	NPC214621
0.9212	High Similarity	NPC5319
0.9202	High Similarity	NPC473644
0.9202	High Similarity	NPC311850
0.9198	High Similarity	NPC170052
0.9198	High Similarity	NPC297987
0.9198	High Similarity	NPC303913
0.9198	High Similarity	NPC135846
0.9198	High Similarity	NPC64305
0.9193	High Similarity	NPC43761
0.9193	High Similarity	NPC73511
0.9187	High Similarity	NPC127406
0.9187	High Similarity	NPC295613
0.9187	High Similarity	NPC473657
0.9182	High Similarity	NPC29763
0.9182	High Similarity	NPC83283
0.9182	High Similarity	NPC143851
0.9182	High Similarity	NPC39360
0.9182	High Similarity	NPC210003
0.9181	High Similarity	NPC470719
0.9181	High Similarity	NPC33083
0.9181	High Similarity	NPC473554
0.9181	High Similarity	NPC295625
0.9176	High Similarity	NPC470718
0.9172	High Similarity	NPC179862
0.9167	High Similarity	NPC144097
0.9167	High Similarity	NPC61904
0.9162	High Similarity	NPC472993
0.9141	High Similarity	NPC131745
0.9141	High Similarity	NPC150164
0.9136	High Similarity	NPC142860
0.9136	High Similarity	NPC97285
0.9136	High Similarity	NPC246469
0.9136	High Similarity	NPC153342
0.9136	High Similarity	NPC271270
0.913	High Similarity	NPC313163
0.913	High Similarity	NPC6985
0.913	High Similarity	NPC258035
0.913	High Similarity	NPC197896
0.913	High Similarity	NPC60966
0.913	High Similarity	NPC161749
0.913	High Similarity	NPC156457
0.9125	High Similarity	NPC99233
0.9123	High Similarity	NPC470416
0.9119	High Similarity	NPC88484
0.9119	High Similarity	NPC259767
0.9112	High Similarity	NPC293626
0.9112	High Similarity	NPC113836
0.9112	High Similarity	NPC196127
0.9112	High Similarity	NPC37668
0.9112	High Similarity	NPC217387

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC188815 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	927
0.2-0.3	1897
0.3-0.4	2701
0.4-0.5	1908
0.5-0.6	927
0.6-0.7	272
0.7-0.8	115
0.8-0.85	25
0.85-0.9	12
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9212	High Similarity	NPD7804	Clinical (unspecified phase)
0.913	High Similarity	NPD4381	Clinical (unspecified phase)
0.8994	High Similarity	NPD7808	Phase 3
0.8935	High Similarity	NPD7251	Discontinued
0.8876	High Similarity	NPD6797	Phase 2
0.8869	High Similarity	NPD7054	Approved
0.8817	High Similarity	NPD7472	Approved
0.878	High Similarity	NPD7075	Discontinued
0.8772	High Similarity	NPD4338	Clinical (unspecified phase)
0.8706	High Similarity	NPD7074	Phase 3
0.865	High Similarity	NPD6801	Discontinued
0.8598	High Similarity	NPD7096	Clinical (unspecified phase)
0.858	High Similarity	NPD6168	Clinical (unspecified phase)
0.858	High Similarity	NPD6166	Phase 2
0.858	High Similarity	NPD6167	Clinical (unspecified phase)
0.8571	High Similarity	NPD5403	Approved
0.8547	High Similarity	NPD7993	Clinical (unspecified phase)
0.8528	High Similarity	NPD4380	Phase 2
0.85	High Similarity	NPD6799	Approved
0.8483	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD3818	Discontinued
0.8476	Intermediate Similarity	NPD7411	Suspended
0.8471	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD5401	Approved
0.84	Intermediate Similarity	NPD8313	Approved
0.84	Intermediate Similarity	NPD8312	Approved
0.8391	Intermediate Similarity	NPD6559	Discontinued
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD5402	Approved
0.8323	Intermediate Similarity	NPD3817	Phase 2
0.8274	Intermediate Similarity	NPD7768	Phase 2
0.8274	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD8455	Phase 2
0.8221	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6599	Discontinued
0.8187	Intermediate Similarity	NPD1549	Phase 2
0.8155	Intermediate Similarity	NPD7819	Suspended
0.8125	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1934	Approved
0.8081	Intermediate Similarity	NPD6959	Discontinued
0.8047	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD3882	Suspended
0.7952	Intermediate Similarity	NPD1512	Approved
0.795	Intermediate Similarity	NPD2796	Approved
0.7941	Intermediate Similarity	NPD2801	Approved
0.7937	Intermediate Similarity	NPD7435	Discontinued
0.7917	Intermediate Similarity	NPD8151	Discontinued
0.7907	Intermediate Similarity	NPD3749	Approved
0.7888	Intermediate Similarity	NPD1510	Phase 2
0.7869	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3751	Discontinued
0.7831	Intermediate Similarity	NPD1511	Approved
0.7829	Intermediate Similarity	NPD3787	Discontinued
0.7809	Intermediate Similarity	NPD5844	Phase 1
0.7805	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD7871	Phase 2
0.7801	Intermediate Similarity	NPD7870	Phase 2
0.7784	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7874	Approved
0.7778	Intermediate Similarity	NPD6777	Approved
0.7778	Intermediate Similarity	NPD6776	Approved
0.7778	Intermediate Similarity	NPD6779	Approved
0.7778	Intermediate Similarity	NPD6778	Approved
0.7778	Intermediate Similarity	NPD6781	Approved
0.7778	Intermediate Similarity	NPD6782	Approved
0.7778	Intermediate Similarity	NPD6780	Approved
0.7758	Intermediate Similarity	NPD3750	Approved
0.775	Intermediate Similarity	NPD1240	Approved
0.7749	Intermediate Similarity	NPD7696	Phase 3
0.7749	Intermediate Similarity	NPD7697	Approved
0.7749	Intermediate Similarity	NPD7698	Approved
0.7736	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.772	Intermediate Similarity	NPD7584	Approved
0.7706	Intermediate Similarity	NPD7458	Discontinued
0.7697	Intermediate Similarity	NPD7473	Discontinued
0.7692	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7685	Pre-registration
0.768	Intermediate Similarity	NPD7701	Phase 2
0.7654	Intermediate Similarity	NPD1607	Approved
0.7653	Intermediate Similarity	NPD7783	Phase 2
0.7653	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4628	Phase 3
0.7647	Intermediate Similarity	NPD1653	Approved
0.764	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD6232	Discontinued
0.7622	Intermediate Similarity	NPD1551	Phase 2
0.7617	Intermediate Similarity	NPD8320	Phase 1
0.7617	Intermediate Similarity	NPD8319	Approved
0.7609	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD7700	Phase 2
0.7579	Intermediate Similarity	NPD7699	Phase 2
0.7571	Intermediate Similarity	NPD7199	Phase 2
0.7563	Intermediate Similarity	NPD7801	Approved
0.7556	Intermediate Similarity	NPD7228	Approved
0.753	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6798	Discontinued
0.7514	Intermediate Similarity	NPD5494	Approved
0.7513	Intermediate Similarity	NPD6535	Approved
0.7513	Intermediate Similarity	NPD6534	Approved
0.75	Intermediate Similarity	NPD7585	Approved
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7488	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1933	Approved
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.7469	Intermediate Similarity	NPD6233	Phase 2
0.7455	Intermediate Similarity	NPD3748	Approved
0.7449	Intermediate Similarity	NPD7583	Approved
0.7429	Intermediate Similarity	NPD1465	Phase 2
0.7423	Intermediate Similarity	NPD6823	Phase 2
0.7418	Intermediate Similarity	NPD7286	Phase 2
0.7384	Intermediate Similarity	NPD920	Approved
0.738	Intermediate Similarity	NPD8434	Phase 2
0.7365	Intermediate Similarity	NPD7266	Discontinued
0.736	Intermediate Similarity	NPD919	Approved
0.7349	Intermediate Similarity	NPD7033	Discontinued
0.7337	Intermediate Similarity	NPD5953	Discontinued
0.7312	Intermediate Similarity	NPD1203	Approved
0.731	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2935	Discontinued
0.7294	Intermediate Similarity	NPD6190	Approved
0.7289	Intermediate Similarity	NPD7097	Phase 1
0.7278	Intermediate Similarity	NPD1652	Phase 2
0.7278	Intermediate Similarity	NPD1243	Approved
0.7273	Intermediate Similarity	NPD37	Approved
0.7267	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6234	Discontinued
0.7251	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD4965	Approved
0.7247	Intermediate Similarity	NPD4967	Phase 2
0.7247	Intermediate Similarity	NPD4966	Approved
0.7209	Intermediate Similarity	NPD7390	Discontinued
0.7204	Intermediate Similarity	NPD7240	Approved
0.72	Intermediate Similarity	NPD3226	Approved
0.7198	Intermediate Similarity	NPD3926	Phase 2
0.7195	Intermediate Similarity	NPD2313	Discontinued
0.7178	Intermediate Similarity	NPD4908	Phase 1
0.717	Intermediate Similarity	NPD1091	Approved
0.7169	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5124	Phase 1
0.7169	Intermediate Similarity	NPD6355	Discontinued
0.7168	Intermediate Similarity	NPD2532	Approved
0.7168	Intermediate Similarity	NPD2533	Approved
0.7168	Intermediate Similarity	NPD2534	Approved
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7126	Intermediate Similarity	NPD6651	Approved
0.7125	Intermediate Similarity	NPD9717	Approved
0.7119	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6213	Phase 3
0.7098	Intermediate Similarity	NPD6212	Phase 3
0.7098	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3268	Approved
0.7088	Intermediate Similarity	NPD1247	Approved
0.7076	Intermediate Similarity	NPD2800	Approved
0.7074	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD230	Phase 1
0.7063	Intermediate Similarity	NPD422	Phase 1
0.7063	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4363	Phase 3
0.7062	Intermediate Similarity	NPD4360	Phase 2
0.7059	Intermediate Similarity	NPD2344	Approved
0.7055	Intermediate Similarity	NPD2798	Approved
0.7037	Intermediate Similarity	NPD3225	Approved
0.7035	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD4287	Approved
0.7006	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1613	Approved
0.6994	Remote Similarity	NPD2797	Approved
0.6994	Remote Similarity	NPD3887	Approved
0.6994	Remote Similarity	NPD2354	Approved
0.6983	Remote Similarity	NPD6844	Discontinued
0.6965	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD447	Suspended
0.6964	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2346	Discontinued
0.6954	Remote Similarity	NPD7440	Discontinued
0.695	Remote Similarity	NPD7680	Approved
0.6946	Remote Similarity	NPD4062	Phase 3
0.6942	Remote Similarity	NPD7930	Approved
0.6941	Remote Similarity	NPD4308	Phase 3
0.6936	Remote Similarity	NPD7003	Approved
0.6918	Remote Similarity	NPD9545	Approved
0.6918	Remote Similarity	NPD1548	Phase 1
0.691	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4288	Approved
0.6905	Remote Similarity	NPD943	Approved
0.6902	Remote Similarity	NPD8127	Discontinued
0.6901	Remote Similarity	NPD6099	Approved
0.6901	Remote Similarity	NPD5404	Approved
0.6901	Remote Similarity	NPD5405	Approved
0.6901	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8059	Phase 3
0.6901	Remote Similarity	NPD5406	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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