NPASS Compound

Structure

CID47521 OpenBabel06191715382D 67 74 0 0 1 0 0 0 0 0999 V2000 0.0000 0.9867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8545 2.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6886 0.6741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4488 -3.5483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0429 -5.2982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7554 -3.1053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3879 0.3367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8545 1.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0077 -0.0400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2620 -2.5795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5371 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7741 -3.2084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8545 1.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6474 0.4415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3812 -3.8710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3584 -6.1996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3353 -3.9035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8545 -0.4933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2857 -0.9867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0077 -1.9334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5183 -4.6031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3728 -4.1098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8545 2.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9254 -0.5052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1268 -3.2249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3397 -6.3027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9340 -4.8049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2445 -1.2193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9401 -2.2561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9196 -5.5045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9528 -4.9080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8545 -1.4800 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.9733 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8545 -1.4800 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7090 0.9867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2620 0.6062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2854 -2.7199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1962 -3.8398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5690 -2.2433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8545 -0.4933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7090 0.9867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.9467 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3283 1.1556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5679 -4.8399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2215 -6.9978 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3166 -3.8004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7090 2.9600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8843 -0.7378 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0592 -3.5476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7410 -7.2041 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5140 -5.6031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5225 -2.1660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6858 -1.6099 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8822 -5.7108 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5514 -5.8094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5634 1.4800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6719 1.5037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1450 -3.6965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0507 -4.3331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4235 -1.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2854 0.7466 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 1.3879 -2.3100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4013 -2.8747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8357 -1.5831 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7090 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 1 13 1 0 0 0 0 2 8 1 0 0 0 0 2 14 2 0 0 0 0 3 9 2 0 0 0 0 3 15 1 0 0 0 0 4 10 2 0 0 0 0 4 16 1 0 0 0 0 5 11 2 0 0 0 0 5 17 1 0 0 0 0 6 12 2 0 0 0 0 6 18 1 0 0 0 0 7 62 1 0 0 0 0 8 36 1 0 0 0 0 9 20 1 0 0 0 0 9 37 1 0 0 0 0 10 21 1 0 0 0 0 10 38 1 0 0 0 0 11 22 1 0 0 0 0 11 39 1 0 0 0 0 12 23 1 0 0 0 0 12 40 1 0 0 0 0 13 24 2 0 0 0 0 13 42 1 0 0 0 0 14 24 1 0 0 0 0 14 43 1 0 0 0 0 15 25 2 0 0 0 0 15 44 1 0 0 0 0 16 26 2 0 0 0 0 16 45 1 0 0 0 0 17 27 2 0 0 0 0 17 46 1 0 0 0 0 18 28 2 0 0 0 0 18 47 1 0 0 0 0 19 7 1 6 0 0 0 19 33 1 0 0 0 0 19 63 1 0 0 0 0 20 21 1 0 0 0 0 20 29 2 0 0 0 0 21 30 2 0 0 0 0 22 23 1 0 0 0 0 22 31 2 0 0 0 0 23 32 2 0 0 0 0 24 48 1 0 0 0 0 25 29 1 0 0 0 0 25 49 1 0 0 0 0 26 30 1 0 0 0 0 26 50 1 0 0 0 0 27 31 1 0 0 0 0 27 51 1 0 0 0 0 28 32 1 0 0 0 0 28 52 1 0 0 0 0 29 53 1 0 0 0 0 30 54 1 0 0 0 0 31 55 1 0 0 0 0 32 56 1 0 0 0 0 33 34 1 0 0 0 0 33 64 1 1 0 0 0 34 35 1 0 0 0 0 34 65 1 6 0 0 0 35 41 1 0 0 0 0 35 66 1 1 0 0 0 36 57 2 0 0 0 0 36 67 1 0 0 0 0 37 58 2 0 0 0 0 37 62 1 0 0 0 0 38 59 2 0 0 0 0 38 64 1 0 0 0 0 39 60 2 0 0 0 0 39 65 1 0 0 0 0 40 61 2 0 0 0 0 40 66 1 0 0 0 0 41 63 1 0 0 0 0 41 67 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	936.09
Volume:	825.057
LogP:	2.137
LogD:	1.138
LogS:	-4.088
# Rotatable Bonds:	3
TPSA:	444.18
# H-Bond Aceptor:	26
# H-Bond Donor:	15
# Rings:	8
# Heavy Atoms:	26

MedChem Properties

QED Drug-Likeness Score:	0.068
Synthetic Accessibility Score:	5.741
Fsp3:	0.146
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-7.232
MDCK Permeability:	6.280230081756599e-06
Pgp-inhibitor:	0.248
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.951
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	89.43428039550781%
Volume Distribution (VD):	0.265
Pgp-substrate:	57.29728317260742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.108
CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.014
CYP2C9-inhibitor:	0.255
CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	11.427
Half-life (T1/2):	0.969

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.125
Drug-inuced Liver Injury (DILI):	0.997
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.962
Carcinogencity:	0.007
Eye Corrosion:	0.003
Eye Irritation:	0.944
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: NPC47521

Natural Product ID:	NPC47521
*Common Name:**	SWRFKGRMQVLMKA-JIZJWZDPSA-N
IUPAC Name:	n.a.
Synonyms:	1(Beta)-O-Galloylpedunculagin
Standard InCHIKey:	SWRFKGRMQVLMKA-JIZJWZDPSA-N
Standard InCHI:	InChI=1S/C41H28O26/c42-13-1-8(2-14(43)24(13)48)36(57)67-41-35-34(65-39(60)11-5-17(46)27(51)31(55)22(11)23-12(40(61)66-35)6-18(47)28(52)32(23)56)33-19(63-41)7-62-37(58)9-3-15(44)25(49)29(53)20(9)21-10(38(59)64-33)4-16(45)26(50)30(21)54/h1-6,19,33-35,41-56H,7H2/t19-,33-,34+,35-,41+/m1/s1
SMILES:	O=C(c1cc(O)c(c(c1)O)O)O[C@@H]1O[C@@H]2COC(=O)c3cc(O)c(c(c3c3c(C(=O)O[C@H]2[C@H]2[C@H]1OC(=O)c1cc(O)c(c(c1c1c(C(=O)O2)cc(c(c1O)O)O)O)O)cc(O)c(c3O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446979
PubChem CID:	73644
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
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodcont.2014.02.001]
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]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193039]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402962]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17685627]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[20467822]
NPO1590	Sinningia aggregata	Species	Gesneriaceae	Eukaryota	Tubers	n.a.	n.a.	PMID[20684540]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21353549]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21384845]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	Leaves	Huangshan, Anhui Province, China	2008-NOV	PMID[21384845]
NPO13504	Lotus japonicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21510636]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22281186]
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]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23632365]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[24063567]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24461297]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[26977531]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27588326]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30379546]
NPO40924	Sanguisorbae radix	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[30497912]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[31301930]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31596079]
NPO6783	Avrainvillea rawsonii	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964790]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8904847]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1934	Strychnos triplinervia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19574	Potentilla kleiniana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25774	Virola multinervia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2346	Agrimonia japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18564	Ligularia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13907	Senecio renardii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2346	Agrimonia japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18564	Ligularia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3199	Balanophora involucrata	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO577	Lactifluus subvellereus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2663	Casimiroa tetrameria	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19574	Potentilla kleiniana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1934	Strychnos triplinervia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25774	Virola multinervia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13907	Senecio renardii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2346	Agrimonia japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19574	Potentilla kleiniana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10389	Larix cajanderi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2663	Casimiroa tetrameria	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4504	Cassia jahnii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10865	Sextonia rubra	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7084	Montezuma speciosissima	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1456	Bersama abyssinica	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2130	Ehretia dicksonii	Species	Ehretiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1590	Sinningia aggregata	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13504	Lotus japonicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14669	Sclerotinia fructigena	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3199	Balanophora involucrata	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2395	Siphonaria australis	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14200	Aristolochia zollingeriana	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9388	Heliomeris multiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11882	Cedrus libani	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14504	Alectoria divergens	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25774	Virola multinervia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14089	Hypericum ascyron	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6072	Andinobates bombetes	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25538	Senegalia pennata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3458	Lupinus verbasciformis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12585	Craspidospermum verticillatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9456	Rubus sanctus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5834	Pellicularia sasakii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15132	Cypholophus friesianus	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12754	Cerinthe minor	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6783	Avrainvillea rawsonii	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14615	Streptomyces paulus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14289	Pieris napi	Species	Pieridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11165	Spirographis spallanzani	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9718	Cyphelium chrysocephalum	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13701	Melaleuca rhaphiophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12234	Khaya ivorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10012	Triaenophora rupestris	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12069	Isaria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12061	Justicia paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19574	Potentilla kleiniana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7169	Nama hispidum	Species	Namaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7383	Puccinia lagenophorae	Species	Pucciniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO173	Aconitum sajanense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1934	Strychnos triplinervia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7752	Beilschmiedia anacardioides	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1661	Bartramia pomiformis	Species	Bartramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15735	Galeocerdo arcticus	Species	Carcharhinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13076	Cephalaria grossheimii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18564	Ligularia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21498	Coccus ilicis	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12414	Penicillium paxilli	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18178	Chelonaplysilla erecta	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16244	Clusia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13907	Senecio renardii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6041	Lithocolletis coryli	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9669	Dictyopteris acrostichoides	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12409	Artemisia jacutica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1507	Cissus quinquefolia	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19172	Vandopsis gigantea	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12910	Ixeris stolonifera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3868	Senecio sinuatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6756	Davallia orientalis	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8829	Baccharis obtusifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6179	Aframomum amaniense	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2346	Agrimonia japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4855	Colchicum speciosum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO577	Lactifluus subvellereus	Species	Russulaceae	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
ED50	5
IC50	1
Others	2

Activity Type	# Activity
Cell Line	6
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT326	Individual Protein	Squalene monooxygenase	Rattus norvegicus	IC50	=	7000.0	nM	PMID[488234]
NPT672	Cell Line	TE-671	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[488235]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[488235]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[488235]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[488235]
NPT804	Cell Line	HT-22	Mus musculus	Inhibition	=	12.7	%	PMID[488236]
NPT804	Cell Line	HT-22	Mus musculus	Inhibition	=	8.5	%	PMID[488236]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.21	ug ml-1	PMID[488235]

☑ 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 NPC47521 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	406
0.1-0.2	1684
0.2-0.3	3603
0.3-0.4	8359
0.4-0.5	9439
0.5-0.6	5367
0.6-0.7	6636
0.7-0.8	6128
0.8-0.85	856
0.85-0.9	153
0.9-0.95	49
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9874	High Similarity	NPC190204
0.9874	High Similarity	NPC261411
0.9874	High Similarity	NPC43918
0.975	High Similarity	NPC311389
0.975	High Similarity	NPC470271
0.975	High Similarity	NPC31034
0.9688	High Similarity	NPC175793
0.963	High Similarity	NPC470272
0.9506	High Similarity	NPC217781
0.95	High Similarity	NPC291957
0.95	High Similarity	NPC14030
0.9444	High Similarity	NPC26536
0.9444	High Similarity	NPC142707
0.9444	High Similarity	NPC49983
0.9444	High Similarity	NPC317671
0.9441	High Similarity	NPC470898
0.9398	High Similarity	NPC472723
0.9383	High Similarity	NPC162169
0.9383	High Similarity	NPC166851
0.9345	High Similarity	NPC8940
0.9313	High Similarity	NPC114791
0.9313	High Similarity	NPC141331
0.9313	High Similarity	NPC210501
0.9313	High Similarity	NPC104222
0.9313	High Similarity	NPC318826
0.9286	High Similarity	NPC80956
0.925	High Similarity	NPC238419
0.925	High Similarity	NPC172419
0.925	High Similarity	NPC474010
0.925	High Similarity	NPC135222
0.9191	High Similarity	NPC40078
0.9191	High Similarity	NPC471091
0.9191	High Similarity	NPC97924
0.9187	High Similarity	NPC239019
0.9187	High Similarity	NPC247629
0.9186	High Similarity	NPC269046
0.9128	High Similarity	NPC237202
0.9128	High Similarity	NPC469649
0.9128	High Similarity	NPC260521
0.9128	High Similarity	NPC65489
0.9123	High Similarity	NPC231254
0.9075	High Similarity	NPC223534
0.9075	High Similarity	NPC290289
0.9075	High Similarity	NPC240200
0.9075	High Similarity	NPC158214
0.907	High Similarity	NPC261623
0.907	High Similarity	NPC469650
0.907	High Similarity	NPC111490
0.9053	High Similarity	NPC297574
0.9023	High Similarity	NPC93065
0.9023	High Similarity	NPC472721
0.9023	High Similarity	NPC31208
0.9023	High Similarity	NPC187632
0.9023	High Similarity	NPC469652
0.9023	High Similarity	NPC160543
0.9023	High Similarity	NPC472724
0.9023	High Similarity	NPC472720
0.9	High Similarity	NPC205037
0.9	High Similarity	NPC16024
0.9	High Similarity	NPC44260
0.9	High Similarity	NPC3746
0.9	High Similarity	NPC61152
0.8983	High Similarity	NPC189312
0.8966	High Similarity	NPC173872
0.8966	High Similarity	NPC119094
0.8953	High Similarity	NPC129533
0.8953	High Similarity	NPC123259
0.8947	High Similarity	NPC198902
0.8914	High Similarity	NPC201814
0.8895	High Similarity	NPC125352
0.8883	High Similarity	NPC174140
0.887	High Similarity	NPC476358
0.8869	High Similarity	NPC149300
0.8864	High Similarity	NPC264302
0.8857	High Similarity	NPC142291
0.8857	High Similarity	NPC477081
0.8857	High Similarity	NPC7839
0.8857	High Similarity	NPC477083
0.8855	High Similarity	NPC469651
0.8824	High Similarity	NPC473550
0.881	High Similarity	NPC473818
0.8786	High Similarity	NPC53680
0.8786	High Similarity	NPC208797
0.8771	High Similarity	NPC3474
0.8765	High Similarity	NPC100251
0.8765	High Similarity	NPC65333
0.8764	High Similarity	NPC477082
0.8758	High Similarity	NPC140151
0.8757	High Similarity	NPC95421
0.8757	High Similarity	NPC198125
0.875	High Similarity	NPC92117
0.8721	High Similarity	NPC79736
0.8721	High Similarity	NPC67629
0.872	High Similarity	NPC134925
0.8713	High Similarity	NPC263119
0.8713	High Similarity	NPC46640
0.8713	High Similarity	NPC34436
0.8713	High Similarity	NPC98583
0.8713	High Similarity	NPC219600
0.8713	High Similarity	NPC166674
0.8706	High Similarity	NPC181778
0.8688	High Similarity	NPC142528
0.8688	High Similarity	NPC120621
0.8688	High Similarity	NPC248257
0.8671	High Similarity	NPC267549
0.8663	High Similarity	NPC171706
0.8631	High Similarity	NPC121290
0.8629	High Similarity	NPC297503
0.8629	High Similarity	NPC97119
0.8629	High Similarity	NPC135831
0.8621	High Similarity	NPC472726
0.8621	High Similarity	NPC472725
0.8606	High Similarity	NPC104983
0.8606	High Similarity	NPC291948
0.8606	High Similarity	NPC88803
0.8606	High Similarity	NPC250436
0.8606	High Similarity	NPC300845
0.8588	High Similarity	NPC105591
0.8563	High Similarity	NPC289346
0.8563	High Similarity	NPC24627
0.8554	High Similarity	NPC289322
0.8554	High Similarity	NPC38779
0.8554	High Similarity	NPC68324
0.8554	High Similarity	NPC114179
0.8554	High Similarity	NPC156818
0.8554	High Similarity	NPC257309
0.8554	High Similarity	NPC160512
0.8547	High Similarity	NPC47140
0.8547	High Similarity	NPC67134
0.8545	High Similarity	NPC472835
0.8545	High Similarity	NPC203757
0.8538	High Similarity	NPC197708
0.8538	High Similarity	NPC658
0.8531	High Similarity	NPC112380
0.8528	High Similarity	NPC252979
0.8523	High Similarity	NPC132111
0.8514	High Similarity	NPC471030
0.8512	High Similarity	NPC266365
0.8509	High Similarity	NPC268366
0.8506	High Similarity	NPC473713
0.8503	High Similarity	NPC87317
0.85	High Similarity	NPC108455
0.8497	Intermediate Similarity	NPC172033
0.8497	Intermediate Similarity	NPC88560
0.8497	Intermediate Similarity	NPC175230
0.8494	Intermediate Similarity	NPC318432
0.8488	Intermediate Similarity	NPC204937
0.8488	Intermediate Similarity	NPC149011
0.8483	Intermediate Similarity	NPC269625
0.8483	Intermediate Similarity	NPC179947
0.8483	Intermediate Similarity	NPC475179
0.848	Intermediate Similarity	NPC311912
0.8466	Intermediate Similarity	NPC170203
0.8466	Intermediate Similarity	NPC469371
0.8462	Intermediate Similarity	NPC33298
0.8462	Intermediate Similarity	NPC90905
0.8462	Intermediate Similarity	NPC285108
0.8462	Intermediate Similarity	NPC4013
0.8457	Intermediate Similarity	NPC113836
0.8457	Intermediate Similarity	NPC476618
0.8457	Intermediate Similarity	NPC476619
0.8457	Intermediate Similarity	NPC37668
0.8457	Intermediate Similarity	NPC253521
0.8457	Intermediate Similarity	NPC293626
0.8457	Intermediate Similarity	NPC217387
0.8457	Intermediate Similarity	NPC476623
0.8457	Intermediate Similarity	NPC196127
0.8457	Intermediate Similarity	NPC476620
0.8457	Intermediate Similarity	NPC476621
0.8457	Intermediate Similarity	NPC476622
0.8457	Intermediate Similarity	NPC258044
0.8457	Intermediate Similarity	NPC267680
0.8452	Intermediate Similarity	NPC24164
0.8452	Intermediate Similarity	NPC53889
0.8443	Intermediate Similarity	NPC472860
0.8439	Intermediate Similarity	NPC38438
0.8439	Intermediate Similarity	NPC102851
0.8439	Intermediate Similarity	NPC5786
0.8438	Intermediate Similarity	NPC121573
0.8438	Intermediate Similarity	NPC190587
0.8438	Intermediate Similarity	NPC229036
0.8438	Intermediate Similarity	NPC22176
0.8438	Intermediate Similarity	NPC226738
0.8436	Intermediate Similarity	NPC473618
0.8434	Intermediate Similarity	NPC156624
0.8434	Intermediate Similarity	NPC172920
0.843	Intermediate Similarity	NPC88557
0.8427	Intermediate Similarity	NPC104910
0.8427	Intermediate Similarity	NPC475352
0.8427	Intermediate Similarity	NPC229817
0.8427	Intermediate Similarity	NPC474093
0.8427	Intermediate Similarity	NPC221140
0.8427	Intermediate Similarity	NPC473686
0.8427	Intermediate Similarity	NPC475220
0.8418	Intermediate Similarity	NPC293227
0.8418	Intermediate Similarity	NPC473717
0.8418	Intermediate Similarity	NPC475662
0.8418	Intermediate Similarity	NPC473631
0.8405	Intermediate Similarity	NPC75945
0.84	Intermediate Similarity	NPC144097

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 NPC47521 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	936
0.2-0.3	1841
0.3-0.4	2791
0.4-0.5	1917
0.5-0.6	943
0.6-0.7	240
0.7-0.8	113
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8606	High Similarity	NPD4868	Clinical (unspecified phase)
0.8547	High Similarity	NPD7993	Clinical (unspecified phase)
0.8167	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD1465	Phase 2
0.809	Intermediate Similarity	NPD8313	Approved
0.809	Intermediate Similarity	NPD8312	Approved
0.8068	Intermediate Similarity	NPD7074	Phase 3
0.8068	Intermediate Similarity	NPD7472	Approved
0.8057	Intermediate Similarity	NPD3818	Discontinued
0.8057	Intermediate Similarity	NPD7228	Approved
0.8034	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6797	Phase 2
0.8011	Intermediate Similarity	NPD5844	Phase 1
0.8011	Intermediate Similarity	NPD7054	Approved
0.801	Intermediate Similarity	NPD8151	Discontinued
0.7978	Intermediate Similarity	NPD7251	Discontinued
0.7965	Intermediate Similarity	NPD6234	Discontinued
0.7933	Intermediate Similarity	NPD7808	Phase 3
0.7931	Intermediate Similarity	NPD6232	Discontinued
0.7907	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6166	Phase 2
0.7841	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD8455	Phase 2
0.7812	Intermediate Similarity	NPD230	Phase 1
0.7797	Intermediate Similarity	NPD7473	Discontinued
0.7778	Intermediate Similarity	NPD37	Approved
0.7771	Intermediate Similarity	NPD6959	Discontinued
0.7746	Intermediate Similarity	NPD4966	Approved
0.7746	Intermediate Similarity	NPD4967	Phase 2
0.7746	Intermediate Similarity	NPD4965	Approved
0.7711	Intermediate Similarity	NPD6190	Approved
0.7705	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7266	Discontinued
0.768	Intermediate Similarity	NPD7685	Pre-registration
0.768	Intermediate Similarity	NPD7240	Approved
0.7674	Intermediate Similarity	NPD1934	Approved
0.767	Intermediate Similarity	NPD7199	Phase 2
0.764	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7390	Discontinued
0.7611	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6559	Discontinued
0.7558	Intermediate Similarity	NPD4380	Phase 2
0.7529	Intermediate Similarity	NPD7819	Suspended
0.75	Intermediate Similarity	NPD3749	Approved
0.7471	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD3751	Discontinued
0.7443	Intermediate Similarity	NPD7768	Phase 2
0.7442	Intermediate Similarity	NPD1653	Approved
0.7436	Intermediate Similarity	NPD8319	Approved
0.7436	Intermediate Similarity	NPD8320	Phase 1
0.743	Intermediate Similarity	NPD3787	Discontinued
0.7429	Intermediate Similarity	NPD2801	Approved
0.7421	Intermediate Similarity	NPD6535	Approved
0.7421	Intermediate Similarity	NPD6534	Approved
0.7412	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7075	Discontinued
0.7396	Intermediate Similarity	NPD7700	Phase 2
0.7396	Intermediate Similarity	NPD7699	Phase 2
0.7386	Intermediate Similarity	NPD3817	Phase 2
0.7385	Intermediate Similarity	NPD7435	Discontinued
0.738	Intermediate Similarity	NPD8150	Discontinued
0.7347	Intermediate Similarity	NPD7871	Phase 2
0.7347	Intermediate Similarity	NPD7870	Phase 2
0.7345	Intermediate Similarity	NPD3882	Suspended
0.7337	Intermediate Similarity	NPD3750	Approved
0.7337	Intermediate Similarity	NPD8166	Discontinued
0.732	Intermediate Similarity	NPD6776	Approved
0.732	Intermediate Similarity	NPD6779	Approved
0.732	Intermediate Similarity	NPD6780	Approved
0.732	Intermediate Similarity	NPD6781	Approved
0.732	Intermediate Similarity	NPD6777	Approved
0.732	Intermediate Similarity	NPD6778	Approved
0.732	Intermediate Similarity	NPD6782	Approved
0.7317	Intermediate Similarity	NPD943	Approved
0.7314	Intermediate Similarity	NPD7411	Suspended
0.731	Intermediate Similarity	NPD1511	Approved
0.7305	Intermediate Similarity	NPD5405	Approved
0.7305	Intermediate Similarity	NPD5404	Approved
0.7305	Intermediate Similarity	NPD5406	Approved
0.7305	Intermediate Similarity	NPD5408	Approved
0.7301	Intermediate Similarity	NPD3764	Approved
0.73	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7783	Phase 2
0.7299	Intermediate Similarity	NPD7458	Discontinued
0.7296	Intermediate Similarity	NPD7680	Approved
0.7288	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7874	Approved
0.725	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD9269	Phase 2
0.7232	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD1512	Approved
0.7222	Intermediate Similarity	NPD5494	Approved
0.7219	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7697	Approved
0.7208	Intermediate Similarity	NPD7698	Approved
0.7208	Intermediate Similarity	NPD7696	Phase 3
0.7191	Intermediate Similarity	NPD5402	Approved
0.7188	Intermediate Similarity	NPD6212	Phase 3
0.7188	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6213	Phase 3
0.7168	Intermediate Similarity	NPD2532	Approved
0.7168	Intermediate Similarity	NPD2534	Approved
0.7168	Intermediate Similarity	NPD2533	Approved
0.715	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD1549	Phase 2
0.7102	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6801	Discontinued
0.7071	Intermediate Similarity	NPD6823	Phase 2
0.7069	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7801	Approved
0.7041	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3748	Approved
0.7041	Intermediate Similarity	NPD1510	Phase 2
0.7035	Intermediate Similarity	NPD7003	Approved
0.7035	Intermediate Similarity	NPD4628	Phase 3
0.7011	Intermediate Similarity	NPD6799	Approved
0.7006	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1613	Approved
0.7	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5403	Approved
0.6981	Remote Similarity	NPD9268	Approved
0.6977	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6599	Discontinued
0.6965	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5401	Approved
0.6867	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7229	Phase 3
0.6839	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5242	Approved
0.6828	Remote Similarity	NPD3926	Phase 2
0.6826	Remote Similarity	NPD3027	Phase 3
0.6816	Remote Similarity	NPD3226	Approved
0.6813	Remote Similarity	NPD5353	Approved
0.6811	Remote Similarity	NPD8127	Discontinued
0.6809	Remote Similarity	NPD7177	Discontinued
0.6805	Remote Similarity	NPD1240	Approved
0.6802	Remote Similarity	NPD2796	Approved
0.6802	Remote Similarity	NPD2935	Discontinued
0.6786	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6674	Discontinued
0.6774	Remote Similarity	NPD5710	Approved
0.6774	Remote Similarity	NPD5711	Approved
0.6753	Remote Similarity	NPD8434	Phase 2
0.6743	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7585	Approved
0.6725	Remote Similarity	NPD1607	Approved
0.6722	Remote Similarity	NPD3455	Phase 2
0.6708	Remote Similarity	NPD9545	Approved
0.6705	Remote Similarity	NPD1551	Phase 2
0.6703	Remote Similarity	NPD919	Approved
0.6699	Remote Similarity	NPD7930	Approved
0.6686	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4287	Approved
0.6683	Remote Similarity	NPD7583	Approved
0.6667	Remote Similarity	NPD1933	Approved
0.6667	Remote Similarity	NPD4908	Phase 1
0.665	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.665	Remote Similarity	NPD5006	Approved
0.665	Remote Similarity	NPD5005	Approved
0.6648	Remote Similarity	NPD6273	Approved
0.6634	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7549	Discontinued
0.663	Remote Similarity	NPD4288	Approved
0.6627	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6099	Approved
0.6609	Remote Similarity	NPD6100	Approved
0.6607	Remote Similarity	NPD9494	Approved
0.6605	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7584	Approved
0.6597	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.659	Remote Similarity	NPD8059	Phase 3
0.659	Remote Similarity	NPD7097	Phase 1
0.659	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6798	Discontinued
0.6587	Remote Similarity	NPD1470	Approved
0.6571	Remote Similarity	NPD2346	Discontinued
0.6571	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.657	Remote Similarity	NPD447	Suspended
0.6557	Remote Similarity	NPD6386	Approved
0.6557	Remote Similarity	NPD6385	Approved
0.6553	Remote Similarity	NPD7999	Approved
0.6545	Remote Similarity	NPD7799	Discontinued
0.6543	Remote Similarity	NPD1247	Approved
0.6535	Remote Similarity	NPD4420	Approved
0.6528	Remote Similarity	NPD5953	Discontinued

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