NPASS Compound

Structure

CID175793 OpenBabel06191715552D 56 61 0 0 1 0 0 0 0 0999 V2000 -0.0000 -5.0000 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 -3.4641 -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 4.7519 0.6832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4954 -3.5963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4067 0.3413 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0619 -0.0405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3061 -2.6144 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 1.7321 -6.0000 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 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7238 0.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4404 -3.9234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3436 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0619 -1.9595 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 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0055 -0.5120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1961 -3.2685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3154 -1.2358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0069 -2.2866 0.0000 C 0 0 0 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 -0.0000 -2.0000 0.0000 C 0 0 1 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 -3.5000 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 3.3061 0.6144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3163 -2.7567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 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 2.5981 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 6.4138 1.1712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6296 -4.9053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -7.5000 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 6.9773 -0.7478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1411 -3.5956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5971 -2.1953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7626 -1.6317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7215 1.5240 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1740 -3.7465 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 2.3163 0.7567 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 1.4067 -2.3413 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 1 8 2 0 0 0 0 1 12 1 0 0 0 0 2 8 1 0 0 0 0 2 13 2 0 0 0 0 3 9 2 0 0 0 0 3 14 1 0 0 0 0 4 9 1 0 0 0 0 4 15 2 0 0 0 0 5 10 2 0 0 0 0 5 16 1 0 0 0 0 6 11 2 0 0 0 0 6 17 1 0 0 0 0 7 52 1 0 0 0 0 8 30 1 0 0 0 0 9 31 1 0 0 0 0 10 19 1 0 0 0 0 10 32 1 0 0 0 0 11 20 1 0 0 0 0 11 33 1 0 0 0 0 12 21 2 0 0 0 0 12 35 1 0 0 0 0 13 21 1 0 0 0 0 13 36 1 0 0 0 0 14 22 2 0 0 0 0 14 37 1 0 0 0 0 15 22 1 0 0 0 0 15 38 1 0 0 0 0 16 23 2 0 0 0 0 16 39 1 0 0 0 0 17 24 2 0 0 0 0 17 40 1 0 0 0 0 18 7 1 6 0 0 0 18 27 1 0 0 0 0 18 53 1 0 0 0 0 19 20 1 0 0 0 0 19 25 2 0 0 0 0 20 26 2 0 0 0 0 21 41 1 0 0 0 0 22 42 1 0 0 0 0 23 25 1 0 0 0 0 23 43 1 0 0 0 0 24 26 1 0 0 0 0 24 44 1 0 0 0 0 25 45 1 0 0 0 0 26 46 1 0 0 0 0 27 28 1 0 0 0 0 27 54 1 1 0 0 0 28 29 1 0 0 0 0 28 55 1 6 0 0 0 29 34 1 0 0 0 0 29 56 1 1 0 0 0 30 47 2 0 0 0 0 30 55 1 0 0 0 0 31 48 2 0 0 0 0 31 56 1 0 0 0 0 32 49 2 0 0 0 0 32 52 1 0 0 0 0 33 50 2 0 0 0 0 33 54 1 0 0 0 0 34 51 1 6 0 0 0 34 53 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	786.09
Volume:	696.483
LogP:	1.574
LogD:	0.686
LogS:	-2.619
# Rotatable Bonds:	6
TPSA:	377.42
# H-Bond Aceptor:	22
# H-Bond Donor:	13
# Rings:	6
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.077
Synthetic Accessibility Score:	5.396
Fsp3:	0.176
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:	-7.115
MDCK Permeability:	6.911509444762487e-06
Pgp-inhibitor:	0.14
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.997
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	88.22297668457031%
Volume Distribution (VD):	0.429
Pgp-substrate:	30.93804168701172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.237
CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.018
CYP2C9-inhibitor:	0.403
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	12.624
Half-life (T1/2):	0.974

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.992
AMES Toxicity:	0.098
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.96
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.926
Respiratory Toxicity:	0.002

Download Data

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

Natural Product: NPC175793

Natural Product ID:	NPC175793
*Common Name:**	YKDNTEQLKGYZHT-JSAIFSMWSA-N
IUPAC Name:	n.a.
Synonyms:	1-Desgalloyleugeniin
Standard InCHIKey:	YKDNTEQLKGYZHT-JSAIFSMWSA-N
Standard InCHI:	InChI=1S/C34H26O22/c35-12-1-8(2-13(36)21(12)41)30(47)55-28-27-18(53-34(51)29(28)56-31(48)9-3-14(37)22(42)15(38)4-9)7-52-32(49)10-5-16(39)23(43)25(45)19(10)20-11(33(50)54-27)6-17(40)24(44)26(20)46/h1-6,18,27-29,34-46,51H,7H2/t18-,27-,28+,29-,34-/m1/s1
SMILES:	O[C@@H]1O[C@@H]2COC(=O)c3cc(O)c(c(c3c3c(C(=O)O[C@H]2[C@@H]([C@H]1OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O)cc(O)c(c3O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450376
PubChem CID:	9918701
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
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s00217-007-0799-1]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1016/j.foodchem.2011.01.077]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932140]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402962]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15620261]
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16124765]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121251]
NPO1590	Sinningia aggregata	Species	Gesneriaceae	Eukaryota	Tubers	n.a.	n.a.	PMID[20684540]
NPO6850	Typha domingensis	Species	Typhaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21417376]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21438588]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21848268]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	Urup Island (4557,9 N; 15044,9 E; depth 66 m)	2008-AUG	PMID[21848268]
NPO20146	Cladiella krempfi	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21861494]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21899269]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22612410]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23822585]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26295595]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[26977531]
NPO5842	Annulohypoxylon truncatum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[28009172]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[31301930]
NPO17226	Burkholderia pyrrocinia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[4955234]
NPO22052	Aspergillus candidus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5391291]
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	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Twig	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO1934	Strychnos triplinervia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO577	Lactifluus subvellereus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22121	Piper arboreum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22624	Clematis tangutica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1934	Strychnos triplinervia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6395	Phedimus kamtschaticus	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29466	Triglochin maritima	Species	Juncaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28912	Astragalus gummifer	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20332	Dioscoreophyllum cumminsii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15735	Galeocerdo arcticus	Species	Carcharhinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2968	Anthopleura xanthogrammica	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1897	Ephedra aphylla	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22763	Cuphea carthagenensis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23759	Litsea zeylanica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21730	Pouzolzia occidentalis	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20972	Oscillatoria princeps	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16414	Thuja plicata	Species	Cupressaceae	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]
NPO23010	Crinum defixum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3756	Munronia delavayi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5842	Annulohypoxylon truncatum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22250	Parastrephia lepidophylla	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]
NPO2395	Siphonaria australis	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO577	Lactifluus subvellereus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO115	Eutreptia viridis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2609	Neonectria candida	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1456	Bersama abyssinica	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6395	Phedimus kamtschaticus	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22568	Aristolochia elegans	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13355	Selinum carvifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21991	Modiolus demissus	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO173	Aconitum sajanense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19899	Crepis foetida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3419	Quercus suber	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4293	Allium neapolitanum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12409	Artemisia jacutica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6072	Andinobates bombetes	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28912	Astragalus gummifer	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9718	Cyphelium chrysocephalum	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19333	Byssothecium obiones	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18463	Plectocephalus chilensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21227	Aglaia elaeagnoidea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8829	Baccharis obtusifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22052	Aspergillus candidus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22635	Penstemon secundiflorus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22381	Euphorbia segetalis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20209	Dorstenia lindeniana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22315	Phlogacanthus thyrsiflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21282	Aplidium orthium	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21420	Phormia regina	Species	Calliphoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21603	Eskemukerjea megacarpum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO291	Suillus bovinus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1934	Strychnos triplinervia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6302	Licaria armeniaca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6130	Mammillaria magnimamma	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22509	Syncolostemon parviflorus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12362	Coreopsis fasciculata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22624	Clematis tangutica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9456	Rubus sanctus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20146	Cladiella krempfi	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2922	Botryosphaeria berengeriana	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4816	Cycas armstrongii	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22121	Piper arboreum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19259	Agrostis epigeios	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1590	Sinningia aggregata	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29466	Triglochin maritima	Species	Juncaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6783	Avrainvillea rawsonii	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7383	Puccinia lagenophorae	Species	Pucciniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22447	Sidastrum acuminatum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22829	Ozoroa insignis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2780	Brenneria rubrifaciens	Species	Pectobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO23953	Zanthoxylum monophyllum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10870	Trichilia hirta	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21473	Urtica triangularis	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22893	Apterostigma dentigerum	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21859	Centaurea nigrescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17226	Burkholderia pyrrocinia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25775	Dasystenella acanthina	Species	Primnoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4504	Cassia jahnii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20842	Beauveria felina	Species	Cordycipitaceae	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]
NPO6850	Typha domingensis	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	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
IC50	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1585	Organism	Microcystis aeruginosa	Microcystis aeruginosa	IC50	=	3700.0	nM	PMID[486875]
NPT1586	Organism	Anabaena flos-aquae	Dolichospermum flos-aquae	IC50	=	9500.0	nM	PMID[486875]

☑ 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 NPC175793 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	396
0.1-0.2	1598
0.2-0.3	3462
0.3-0.4	7969
0.4-0.5	9714
0.5-0.6	5483
0.6-0.7	6374
0.7-0.8	6467
0.8-0.85	978
0.85-0.9	186
0.9-0.95	52
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC311389
0.9936	High Similarity	NPC470271
0.9811	High Similarity	NPC470272
0.981	High Similarity	NPC261411
0.981	High Similarity	NPC190204
0.981	High Similarity	NPC43918
0.981	High Similarity	NPC31034
0.9688	High Similarity	NPC47521
0.9682	High Similarity	NPC291957
0.9682	High Similarity	NPC14030
0.962	High Similarity	NPC470898
0.9571	High Similarity	NPC472723
0.9487	High Similarity	NPC247629
0.9487	High Similarity	NPC239019
0.9455	High Similarity	NPC80956
0.9441	High Similarity	NPC217781
0.9437	High Similarity	NPC166851
0.9437	High Similarity	NPC162169
0.9427	High Similarity	NPC172419
0.9427	High Similarity	NPC238419
0.9379	High Similarity	NPC49983
0.9379	High Similarity	NPC317671
0.9379	High Similarity	NPC142707
0.9379	High Similarity	NPC26536
0.9304	High Similarity	NPC474010
0.9304	High Similarity	NPC135222
0.9286	High Similarity	NPC231254
0.9281	High Similarity	NPC8940
0.9245	High Similarity	NPC318826
0.9245	High Similarity	NPC210501
0.9245	High Similarity	NPC114791
0.9245	High Similarity	NPC141331
0.9245	High Similarity	NPC104222
0.9231	High Similarity	NPC111490
0.9231	High Similarity	NPC261623
0.9231	High Similarity	NPC469650
0.9226	High Similarity	NPC123259
0.9226	High Similarity	NPC129533
0.9217	High Similarity	NPC297574
0.9176	High Similarity	NPC65489
0.9172	High Similarity	NPC3746
0.9172	High Similarity	NPC205037
0.9172	High Similarity	NPC61152
0.9172	High Similarity	NPC44260
0.9172	High Similarity	NPC16024
0.9123	High Similarity	NPC477083
0.9123	High Similarity	NPC477081
0.9123	High Similarity	NPC119094
0.9123	High Similarity	NPC269046
0.9123	High Similarity	NPC173872
0.9107	High Similarity	NPC198902
0.907	High Similarity	NPC472721
0.907	High Similarity	NPC31208
0.907	High Similarity	NPC160543
0.907	High Similarity	NPC93065
0.907	High Similarity	NPC472720
0.907	High Similarity	NPC469652
0.907	High Similarity	NPC472724
0.9064	High Similarity	NPC260521
0.9064	High Similarity	NPC237202
0.9064	High Similarity	NPC469649
0.9017	High Similarity	NPC264302
0.9012	High Similarity	NPC223534
0.9012	High Similarity	NPC240200
0.9012	High Similarity	NPC290289
0.9012	High Similarity	NPC7839
0.9012	High Similarity	NPC158214
0.9012	High Similarity	NPC142291
0.8974	High Similarity	NPC248257
0.8974	High Similarity	NPC142528
0.8974	High Similarity	NPC120621
0.896	High Similarity	NPC187632
0.896	High Similarity	NPC201814
0.8941	High Similarity	NPC208797
0.8941	High Similarity	NPC53680
0.8924	High Similarity	NPC140151
0.8922	High Similarity	NPC65333
0.8917	High Similarity	NPC92117
0.8916	High Similarity	NPC95421
0.8916	High Similarity	NPC198125
0.8914	High Similarity	NPC477082
0.8914	High Similarity	NPC476358
0.8908	High Similarity	NPC40078
0.8908	High Similarity	NPC97924
0.8908	High Similarity	NPC471091
0.8902	High Similarity	NPC469651
0.8876	High Similarity	NPC79736
0.8876	High Similarity	NPC67629
0.8869	High Similarity	NPC166674
0.8869	High Similarity	NPC473550
0.8869	High Similarity	NPC46640
0.8869	High Similarity	NPC263119
0.8869	High Similarity	NPC34436
0.8869	High Similarity	NPC219600
0.8862	High Similarity	NPC181778
0.8855	High Similarity	NPC473818
0.8834	High Similarity	NPC24627
0.883	High Similarity	NPC125352
0.8824	High Similarity	NPC267549
0.882	High Similarity	NPC203757
0.8817	High Similarity	NPC171706
0.881	High Similarity	NPC100251
0.8802	High Similarity	NPC149300
0.879	High Similarity	NPC268366
0.8788	High Similarity	NPC121290
0.8779	High Similarity	NPC135831
0.8779	High Similarity	NPC297503
0.8779	High Similarity	NPC97119
0.8765	High Similarity	NPC134925
0.8765	High Similarity	NPC291948
0.8765	High Similarity	NPC88803
0.8765	High Similarity	NPC300845
0.8765	High Similarity	NPC250436
0.8765	High Similarity	NPC104983
0.8757	High Similarity	NPC98583
0.8736	High Similarity	NPC105591
0.872	High Similarity	NPC24164
0.872	High Similarity	NPC289346
0.8718	High Similarity	NPC190587
0.8718	High Similarity	NPC226738
0.8718	High Similarity	NPC121573
0.8718	High Similarity	NPC229036
0.8718	High Similarity	NPC22176
0.8712	High Similarity	NPC160512
0.8712	High Similarity	NPC156818
0.8712	High Similarity	NPC38779
0.8712	High Similarity	NPC289322
0.8712	High Similarity	NPC257309
0.8712	High Similarity	NPC68324
0.8712	High Similarity	NPC114179
0.8708	High Similarity	NPC189312
0.8708	High Similarity	NPC3474
0.8698	High Similarity	NPC47140
0.8698	High Similarity	NPC67134
0.869	High Similarity	NPC658
0.869	High Similarity	NPC197708
0.8688	High Similarity	NPC252979
0.8679	High Similarity	NPC75945
0.8671	High Similarity	NPC132111
0.8667	High Similarity	NPC266365
0.8663	High Similarity	NPC471030
0.8662	High Similarity	NPC108455
0.8659	High Similarity	NPC87317
0.8655	High Similarity	NPC473713
0.865	High Similarity	NPC318432
0.8647	High Similarity	NPC175230
0.8647	High Similarity	NPC88560
0.8647	High Similarity	NPC172033
0.8639	High Similarity	NPC204937
0.8639	High Similarity	NPC149011
0.8629	High Similarity	NPC179947
0.8629	High Similarity	NPC269625
0.8616	High Similarity	NPC81835
0.8614	High Similarity	NPC4013
0.8614	High Similarity	NPC33298
0.8614	High Similarity	NPC476372
0.8614	High Similarity	NPC285108
0.8614	High Similarity	NPC90905
0.8614	High Similarity	NPC476371
0.8613	High Similarity	NPC170203
0.8613	High Similarity	NPC469371
0.8611	High Similarity	NPC174140
0.8606	High Similarity	NPC53889
0.8605	High Similarity	NPC253521
0.8605	High Similarity	NPC113836
0.8605	High Similarity	NPC37668
0.8605	High Similarity	NPC258044
0.8605	High Similarity	NPC476619
0.8605	High Similarity	NPC196127
0.8605	High Similarity	NPC293626
0.8605	High Similarity	NPC476618
0.8605	High Similarity	NPC267680
0.8605	High Similarity	NPC476620
0.8605	High Similarity	NPC476622
0.8605	High Similarity	NPC476621
0.8605	High Similarity	NPC217387
0.8605	High Similarity	NPC476623
0.8598	High Similarity	NPC472860
0.8589	High Similarity	NPC472835
0.8589	High Similarity	NPC172920
0.8589	High Similarity	NPC156624
0.8588	High Similarity	NPC102851
0.8588	High Similarity	NPC38438
0.8588	High Similarity	NPC5786
0.858	High Similarity	NPC473618
0.8571	High Similarity	NPC104910
0.8571	High Similarity	NPC112380
0.8571	High Similarity	NPC474093
0.8555	High Similarity	NPC472726
0.8555	High Similarity	NPC472725
0.8547	High Similarity	NPC472992
0.8547	High Similarity	NPC472991
0.8547	High Similarity	NPC144097
0.8547	High Similarity	NPC61904
0.8545	High Similarity	NPC471750
0.8538	High Similarity	NPC472993
0.8529	High Similarity	NPC476365
0.8528	High Similarity	NPC125487
0.8528	High Similarity	NPC238672
0.8528	High Similarity	NPC144801

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 NPC175793 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	907
0.2-0.3	1834
0.3-0.4	2759
0.4-0.5	1908
0.5-0.6	993
0.6-0.7	262
0.7-0.8	122
0.8-0.85	13
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.881	High Similarity	NPD7993	Clinical (unspecified phase)
0.8765	High Similarity	NPD4868	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD1465	Phase 2
0.8256	Intermediate Similarity	NPD5844	Phase 1
0.8208	Intermediate Similarity	NPD7074	Phase 3
0.8208	Intermediate Similarity	NPD7472	Approved
0.8198	Intermediate Similarity	NPD3818	Discontinued
0.8198	Intermediate Similarity	NPD7228	Approved
0.8171	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD6797	Phase 2
0.815	Intermediate Similarity	NPD7054	Approved
0.8125	Intermediate Similarity	NPD8312	Approved
0.8125	Intermediate Similarity	NPD8313	Approved
0.8114	Intermediate Similarity	NPD7251	Discontinued
0.8101	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD6166	Phase 2
0.8081	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD6232	Discontinued
0.8068	Intermediate Similarity	NPD7808	Phase 3
0.8047	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD8151	Discontinued
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6234	Discontinued
0.7976	Intermediate Similarity	NPD8455	Phase 2
0.7963	Intermediate Similarity	NPD6190	Approved
0.7962	Intermediate Similarity	NPD230	Phase 1
0.7931	Intermediate Similarity	NPD7473	Discontinued
0.7917	Intermediate Similarity	NPD37	Approved
0.7907	Intermediate Similarity	NPD6959	Discontinued
0.7882	Intermediate Similarity	NPD4967	Phase 2
0.7882	Intermediate Similarity	NPD4965	Approved
0.7882	Intermediate Similarity	NPD4966	Approved
0.7826	Intermediate Similarity	NPD7266	Discontinued
0.7811	Intermediate Similarity	NPD1934	Approved
0.7809	Intermediate Similarity	NPD7685	Pre-registration
0.7809	Intermediate Similarity	NPD7240	Approved
0.7803	Intermediate Similarity	NPD7199	Phase 2
0.7798	Intermediate Similarity	NPD4380	Phase 2
0.7771	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD6559	Discontinued
0.7661	Intermediate Similarity	NPD7819	Suspended
0.7651	Intermediate Similarity	NPD7390	Discontinued
0.763	Intermediate Similarity	NPD3749	Approved
0.7614	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD8150	Discontinued
0.7584	Intermediate Similarity	NPD3751	Discontinued
0.7574	Intermediate Similarity	NPD1653	Approved
0.7572	Intermediate Similarity	NPD7768	Phase 2
0.7558	Intermediate Similarity	NPD2801	Approved
0.7557	Intermediate Similarity	NPD3787	Discontinued
0.7552	Intermediate Similarity	NPD8320	Phase 1
0.7552	Intermediate Similarity	NPD8319	Approved
0.754	Intermediate Similarity	NPD6535	Approved
0.754	Intermediate Similarity	NPD6534	Approved
0.7529	Intermediate Similarity	NPD7075	Discontinued
0.7514	Intermediate Similarity	NPD3817	Phase 2
0.7513	Intermediate Similarity	NPD7699	Phase 2
0.7513	Intermediate Similarity	NPD7700	Phase 2
0.75	Intermediate Similarity	NPD7435	Discontinued
0.7471	Intermediate Similarity	NPD3882	Suspended
0.747	Intermediate Similarity	NPD3750	Approved
0.7453	Intermediate Similarity	NPD943	Approved
0.7442	Intermediate Similarity	NPD7411	Suspended
0.744	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1511	Approved
0.7439	Intermediate Similarity	NPD5406	Approved
0.7439	Intermediate Similarity	NPD5405	Approved
0.7439	Intermediate Similarity	NPD5408	Approved
0.7439	Intermediate Similarity	NPD5404	Approved
0.7438	Intermediate Similarity	NPD3764	Approved
0.7435	Intermediate Similarity	NPD6779	Approved
0.7435	Intermediate Similarity	NPD6776	Approved
0.7435	Intermediate Similarity	NPD6780	Approved
0.7435	Intermediate Similarity	NPD6781	Approved
0.7435	Intermediate Similarity	NPD6782	Approved
0.7435	Intermediate Similarity	NPD6777	Approved
0.7435	Intermediate Similarity	NPD6778	Approved
0.7414	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5402	Approved
0.7411	Intermediate Similarity	NPD7783	Phase 2
0.7411	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7680	Approved
0.7382	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD9269	Phase 2
0.7371	Intermediate Similarity	NPD7871	Phase 2
0.7371	Intermediate Similarity	NPD7870	Phase 2
0.7365	Intermediate Similarity	NPD8166	Discontinued
0.736	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7874	Approved
0.7356	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1512	Approved
0.7349	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5494	Approved
0.7326	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7697	Approved
0.732	Intermediate Similarity	NPD7696	Phase 3
0.732	Intermediate Similarity	NPD7698	Approved
0.7302	Intermediate Similarity	NPD6212	Phase 3
0.7302	Intermediate Similarity	NPD6213	Phase 3
0.7302	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6801	Discontinued
0.7294	Intermediate Similarity	NPD2534	Approved
0.7294	Intermediate Similarity	NPD2533	Approved
0.7294	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD2532	Approved
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4628	Phase 3
0.7259	Intermediate Similarity	NPD7701	Phase 2
0.7246	Intermediate Similarity	NPD1549	Phase 2
0.7239	Intermediate Similarity	NPD1613	Approved
0.7239	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7458	Discontinued
0.7209	Intermediate Similarity	NPD5403	Approved
0.7186	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6823	Phase 2
0.7169	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD3748	Approved
0.7169	Intermediate Similarity	NPD1510	Phase 2
0.715	Intermediate Similarity	NPD7801	Approved
0.7135	Intermediate Similarity	NPD6799	Approved
0.7115	Intermediate Similarity	NPD9268	Approved
0.7101	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5401	Approved
0.7087	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6599	Discontinued
0.7059	Intermediate Similarity	NPD7003	Approved
0.7055	Intermediate Similarity	NPD3027	Phase 3
0.7037	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD8127	Discontinued
0.6994	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7229	Phase 3
0.6959	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8434	Phase 2
0.694	Remote Similarity	NPD3926	Phase 2
0.694	Remote Similarity	NPD5242	Approved
0.6932	Remote Similarity	NPD3226	Approved
0.6928	Remote Similarity	NPD1240	Approved
0.6927	Remote Similarity	NPD5353	Approved
0.6923	Remote Similarity	NPD2796	Approved
0.6923	Remote Similarity	NPD2935	Discontinued
0.6919	Remote Similarity	NPD7177	Discontinued
0.6909	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6674	Discontinued
0.6885	Remote Similarity	NPD5710	Approved
0.6885	Remote Similarity	NPD5711	Approved
0.686	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6273	Approved
0.6845	Remote Similarity	NPD1607	Approved
0.6837	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD3455	Phase 2
0.6835	Remote Similarity	NPD9545	Approved
0.6832	Remote Similarity	NPD7585	Approved
0.6824	Remote Similarity	NPD1551	Phase 2
0.6813	Remote Similarity	NPD919	Approved
0.6796	Remote Similarity	NPD7930	Approved
0.6788	Remote Similarity	NPD4908	Phase 1
0.6788	Remote Similarity	NPD4287	Approved
0.6782	Remote Similarity	NPD7583	Approved
0.674	Remote Similarity	NPD4288	Approved
0.6737	Remote Similarity	NPD7549	Discontinued
0.6734	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD9494	Approved
0.6725	Remote Similarity	NPD6100	Approved
0.6725	Remote Similarity	NPD6099	Approved
0.6707	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6798	Discontinued
0.6707	Remote Similarity	NPD1470	Approved
0.6706	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7097	Phase 1
0.6705	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7584	Approved
0.6698	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1933	Approved
0.6686	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD447	Suspended
0.6686	Remote Similarity	NPD2346	Discontinued
0.6682	Remote Similarity	NPD8059	Phase 3
0.6682	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6385	Approved
0.6667	Remote Similarity	NPD5005	Approved
0.6667	Remote Similarity	NPD5006	Approved
0.6667	Remote Similarity	NPD6386	Approved
0.665	Remote Similarity	NPD7999	Approved
0.6649	Remote Similarity	NPD1247	Approved
0.6649	Remote Similarity	NPD7799	Discontinued
0.6647	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5953	Discontinued
0.6629	Remote Similarity	NPD920	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