NPASS Compound

Structure

NPC266580 OpenBabel06302215322D 79 87 0 0 1 0 0 0 0 0999 V2000 -3.3858 2.9322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3858 1.9548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5393 1.4661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6929 1.9548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8464 1.4661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8464 0.4887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6929 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5393 0.4887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3858 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6929 -0.9774 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8464 -1.4661 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8464 -2.4435 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6929 -2.9322 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5393 -2.4435 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3858 -2.9322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3858 -3.9095 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2322 -4.3982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2322 -5.3756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0786 -3.9095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0786 -2.9322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9251 -2.4435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7715 -2.9322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7715 -3.9095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9251 -4.3982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9251 -5.3756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6180 -4.3982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6180 -2.4435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9251 -1.4661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7715 -0.9774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6180 -1.4661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4644 -0.9774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4644 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9531 0.8464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7995 1.3351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7995 2.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9531 2.8012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1067 2.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1067 1.3351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2602 0.8464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2602 2.8012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9531 3.7786 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7769 1.3351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0299 2.2792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.6234 0.8464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.1121 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1121 -0.9774 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.6234 -1.8238 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.7769 -2.3125 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.3299 -1.6010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.6074 -0.8079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.4005 -0.5303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9163 -0.1167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1692 0.8273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7870 2.2096 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0574 1.3333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7485 0.6422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.6926 0.8951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.9456 1.8392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.2545 2.5303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3104 2.2774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5074 3.4744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.8897 2.0922 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.3837 0.2040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3586 -1.7104 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7995 -2.3125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9531 -1.8238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2620 -2.5149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.3145 -2.5149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6180 0.4887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7715 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9251 0.4887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6180 1.4661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5393 -1.4661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6929 -3.9095 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9774 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8464 0.4887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6929 2.9322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 8 2 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 4 79 1 0 0 0 0 5 6 1 0 0 0 0 6 77 1 0 0 0 0 6 7 2 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 10 7 1 1 0 0 0 10 11 1 0 0 0 0 10 73 1 0 0 0 0 11 12 1 0 0 0 0 11 76 1 6 0 0 0 12 13 1 0 0 0 0 12 75 1 6 0 0 0 13 14 1 0 0 0 0 13 74 1 6 0 0 0 14 15 1 6 0 0 0 14 73 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 19 24 2 0 0 0 0 19 20 1 0 0 0 0 20 21 2 0 0 0 0 21 22 1 0 0 0 0 21 28 1 0 0 0 0 22 23 2 0 0 0 0 22 27 1 0 0 0 0 23 24 1 0 0 0 0 23 26 1 0 0 0 0 24 25 1 0 0 0 0 28 29 1 0 0 0 0 29 70 2 0 0 0 0 29 30 1 0 0 0 0 30 31 2 0 0 0 0 31 66 1 0 0 0 0 31 32 1 0 0 0 0 32 33 1 0 0 0 0 32 69 2 0 0 0 0 33 38 2 0 0 0 0 33 34 1 0 0 0 0 34 35 2 0 0 0 0 34 42 1 0 0 0 0 35 36 1 0 0 0 0 36 37 2 0 0 0 0 36 41 1 0 0 0 0 37 38 1 0 0 0 0 37 40 1 0 0 0 0 38 39 1 0 0 0 0 42 43 2 0 0 0 0 42 44 1 0 0 0 0 44 45 1 0 0 0 0 46 45 1 1 0 0 0 46 47 1 0 0 0 0 46 51 1 0 0 0 0 47 48 1 0 0 0 0 47 68 1 6 0 0 0 48 49 1 0 0 0 0 48 65 1 1 0 0 0 49 50 1 0 0 0 0 49 64 1 6 0 0 0 50 51 1 0 0 0 0 50 52 1 1 0 0 0 52 53 1 0 0 0 0 53 54 2 0 0 0 0 53 55 1 0 0 0 0 55 60 2 0 0 0 0 55 56 1 0 0 0 0 56 57 2 0 0 0 0 57 58 1 0 0 0 0 57 63 1 0 0 0 0 58 59 2 0 0 0 0 58 62 1 0 0 0 0 59 60 1 0 0 0 0 59 61 1 0 0 0 0 65 66 1 0 0 0 0 66 67 2 0 0 0 0 69 70 1 0 0 0 0 69 72 1 0 0 0 0 70 71 1 0 0 0 0 76 77 1 0 0 0 0 77 78 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1112.16
Volume:	981.523
LogP:	1.56
LogD:	1.105
LogS:	-2.822
# Rotatable Bonds:	10
TPSA:	512.33
# H-Bond Aceptor:	31
# H-Bond Donor:	17
# Rings:	9
# Heavy Atoms:	31

MedChem Properties

QED Drug-Likeness Score:	0.055
Synthetic Accessibility Score:	7.412
Fsp3:	0.271
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-7.234
MDCK Permeability:	1.7552576537127607e-05
Pgp-inhibitor:	0.428
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.09
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	87.17689514160156%
Volume Distribution (VD):	0.328
Pgp-substrate:	105.52314758300781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.02
CYP2C9-inhibitor:	0.203
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	5.218
Half-life (T1/2):	0.968

ADMET: Toxicity

hERG Blockers:	0.201
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.96
Carcinogencity:	0.008
Eye Corrosion:	0.003
Eye Irritation:	0.915
Respiratory Toxicity:	0.001

Download Data

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

Natural Product: NPC266580

Natural Product ID:	NPC266580
*Common Name:**	YRQJXXJAAXIXBS-DWVCRCDGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YRQJXXJAAXIXBS-DWVCRCDGSA-N
Standard InCHI:	InChI=1S/C48H40O31/c1-71-39-18(52)5-12-25(35(39)62)40-42(78-46(12)69)37(64)31(58)21(75-40)8-73-45(68)14-7-20(30(57)36(63)26(14)53)74-19-6-13-24(34(61)29(19)56)23-11(4-17(51)28(55)33(23)60)44(67)72-9-22-32(59)41(77-47(13)70)38(65)48(76-22)79-43(66)10-2-15(49)27(54)16(50)3-10/h2-7,21-22,31-32,37-38,40-42,48-65H,8-9H2,1H3/t21-,22+,31+,32+,37+,38+,40-,41-,42+,48-/m0/s1
SMILES:	COc1c(cc2c(c1O)[C@H]1[C@@H]([C@@H]([C@@H]([C@H](COC(=O)c3cc(c(c(c3O)O)O)Oc3cc4c(-c5c(cc(c(c5O)O)O)C(=O)OC[C@@H]5[C@H]([C@@H]([C@H]([C@@H](O5)OC(=O)c5cc(c(c(c5)O)O)O)O)OC4=O)O)c(c3O)O)O1)O)O)OC2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757709]
NPO2130	Ehretia dicksonii	Species	Ehretiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10830513]
NPO2130	Ehretia dicksonii	Species	Ehretiaceae	Eukaryota	n.a.	twig	n.a.	PMID[10830513]
NPO2130	Ehretia dicksonii	Species	Ehretiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10830513]
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193039]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17685627]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21353549]
NPO13504	Lotus japonicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21510636]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23078294]
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23210623]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23513740]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30379546]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31596079]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13907	Senecio renardii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25774	Virola multinervia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3199	Balanophora involucrata	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13907	Senecio renardii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25774	Virola multinervia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3458	Lupinus verbasciformis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1661	Bartramia pomiformis	Species	Bartramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14615	Streptomyces paulus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13907	Senecio renardii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12234	Khaya ivorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12910	Ixeris stolonifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13504	Lotus japonicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13076	Cephalaria grossheimii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14200	Aristolochia zollingeriana	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12061	Justicia paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14504	Alectoria divergens	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21498	Coccus ilicis	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9669	Dictyopteris acrostichoides	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2130	Ehretia dicksonii	Species	Ehretiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12754	Cerinthe minor	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3199	Balanophora involucrata	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12585	Craspidospermum verticillatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14289	Pieris napi	Species	Pieridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25774	Virola multinervia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10012	Triaenophora rupestris	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6179	Aframomum amaniense	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7169	Nama hispidum	Species	Namaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7752	Beilschmiedia anacardioides	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12414	Penicillium paxilli	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10389	Larix cajanderi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13701	Melaleuca rhaphiophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10865	Sextonia rubra	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11882	Cedrus libani	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12069	Isaria felina	Species	Cordycipitaceae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC266580 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	439
0.1-0.2	1867
0.2-0.3	4043
0.3-0.4	9141
0.4-0.5	8704
0.5-0.6	5049
0.6-0.7	5896
0.7-0.8	5761
0.8-0.85	1042
0.85-0.9	611
0.9-0.95	109
0.95-1	35

Similarity Score	Similarity Level	Natural Product ID

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 NPC266580 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	389
0.1-0.2	992
0.2-0.3	2062
0.3-0.4	2701
0.4-0.5	1798
0.5-0.6	809
0.6-0.7	270
0.7-0.8	104
0.8-0.85	14
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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