NPASS Compound

Structure

CID190204 OpenBabel06191715572D 67 73 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 2.5981 -4.5000 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 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 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 1 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 3.4641 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 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 5.1962 -5.0000 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 -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 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 -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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 1 15 1 0 0 0 0 2 10 1 0 0 0 0 2 16 2 0 0 0 0 3 11 2 0 0 0 0 3 17 1 0 0 0 0 4 11 1 0 0 0 0 4 18 2 0 0 0 0 5 12 2 0 0 0 0 5 19 1 0 0 0 0 6 12 1 0 0 0 0 6 20 2 0 0 0 0 7 13 2 0 0 0 0 7 21 1 0 0 0 0 8 14 2 0 0 0 0 8 22 1 0 0 0 0 9 62 1 0 0 0 0 10 36 1 0 0 0 0 11 37 1 0 0 0 0 12 38 1 0 0 0 0 13 24 1 0 0 0 0 13 39 1 0 0 0 0 14 25 1 0 0 0 0 14 40 1 0 0 0 0 15 26 2 0 0 0 0 15 42 1 0 0 0 0 16 26 1 0 0 0 0 16 43 1 0 0 0 0 17 27 2 0 0 0 0 17 44 1 0 0 0 0 18 27 1 0 0 0 0 18 45 1 0 0 0 0 19 28 2 0 0 0 0 19 46 1 0 0 0 0 20 28 1 0 0 0 0 20 47 1 0 0 0 0 21 29 2 0 0 0 0 21 48 1 0 0 0 0 22 30 2 0 0 0 0 22 49 1 0 0 0 0 23 9 1 1 0 0 0 23 33 1 0 0 0 0 23 63 1 0 0 0 0 24 25 1 0 0 0 0 24 31 2 0 0 0 0 25 32 2 0 0 0 0 26 50 1 0 0 0 0 27 51 1 0 0 0 0 28 52 1 0 0 0 0 29 31 1 0 0 0 0 29 53 1 0 0 0 0 30 32 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 6 0 0 0 34 35 1 0 0 0 0 34 65 1 1 0 0 0 35 41 1 0 0 0 0 35 66 1 6 0 0 0 36 57 2 0 0 0 0 36 65 1 0 0 0 0 37 58 2 0 0 0 0 37 66 1 0 0 0 0 38 59 2 0 0 0 0 38 67 1 0 0 0 0 39 60 2 0 0 0 0 39 62 1 0 0 0 0 40 61 2 0 0 0 0 40 64 1 0 0 0 0 41 63 1 0 0 0 0 41 67 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	938.1
Volume:	833.613
LogP:	2.145
LogD:	1.149
LogS:	-3.078
# Rotatable Bonds:	9
TPSA:	444.18
# H-Bond Aceptor:	26
# H-Bond Donor:	15
# Rings:	7
# Heavy Atoms:	26

MedChem Properties

QED Drug-Likeness Score:	0.065
Synthetic Accessibility Score:	5.589
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:	-7.256
MDCK Permeability:	7.883221769589e-06
Pgp-inhibitor:	0.264
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	87.5580062866211%
Volume Distribution (VD):	0.247
Pgp-substrate:	44.58602523803711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.525
CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.012
CYP2C9-inhibitor:	0.251
CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	13.534
Half-life (T1/2):	0.977

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.125
Drug-inuced Liver Injury (DILI):	0.993
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.972
Carcinogencity:	0.007
Eye Corrosion:	0.003
Eye Irritation:	0.953
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: NPC190204

Natural Product ID:	NPC190204
*Common Name:**	Eugeniin
IUPAC Name:	n.a.
Synonyms:	Eugeniin
Standard InCHIKey:	JCGHAEBIBSEQAD-UUUCSUBKSA-N
Standard InCHI:	InChI=1S/C41H30O26/c42-15-1-10(2-16(43)26(15)50)36(57)65-34-33-23(9-62-39(60)13-7-21(48)29(53)31(55)24(13)25-14(40(61)64-33)8-22(49)30(54)32(25)56)63-41(67-38(59)12-5-19(46)28(52)20(47)6-12)35(34)66-37(58)11-3-17(44)27(51)18(45)4-11/h1-8,23,33-35,41-56H,9H2/t23-,33-,34+,35-,41+/m1/s1
SMILES:	O=C(c1cc(O)c(c(c1)O)O)O[C@@H]1[C@@H](OC(=O)c2cc(O)c(c(c2)O)O)[C@@H](O[C@H]2[C@H]1OC(=O)c1cc(O)c(c(c1c1c(C(=O)OC2)cc(c(c1O)O)O)O)O)OC(=O)c1cc(O)c(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450745
PubChem CID:	442679
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]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402962]
NPO16699	Agave utahensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19645463]
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]
NPO6850	Typha domingensis	Species	Typhaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21417376]
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]
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]
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]
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	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]
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]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10884	Glycyrrhiza squamulosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16775	Thermopsis lanceolata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1934	Strychnos triplinervia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27015	Valeriana hardwickii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1524	Rosa rugosa	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]
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]
NPO16775	Thermopsis lanceolata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO577	Lactifluus subvellereus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10884	Glycyrrhiza squamulosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27015	Valeriana hardwickii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	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]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10884	Glycyrrhiza squamulosa	Species	Fabaceae	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]
NPO16775	Thermopsis lanceolata	Species	Fabaceae	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]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	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]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7383	Puccinia lagenophorae	Species	Pucciniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3756	Munronia delavayi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6850	Typha domingensis	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4504	Cassia jahnii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4816	Cycas armstrongii	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7720	Cyathocline purpurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10870	Trichilia hirta	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO577	Lactifluus subvellereus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14669	Sclerotinia fructigena	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2609	Neonectria candida	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2968	Anthopleura xanthogrammica	Species	Actiniidae	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]
NPO16207	Acacia glaucescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12393	Xanthoparmelia subincerta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4293	Allium neapolitanum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8606	Mallotus repandus	Species	Euphorbiaceae	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]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6072	Andinobates bombetes	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6302	Licaria armeniaca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18463	Plectocephalus chilensis	Species	Asteraceae	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]
NPO16102	Senecio chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12218	Pulicaria wightiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4754	Yucca flexilis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15984	Blainvillea rhomboidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25775	Dasystenella acanthina	Species	Primnoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1897	Ephedra aphylla	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9718	Cyphelium chrysocephalum	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2395	Siphonaria australis	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13938	Plantago alpina	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15735	Galeocerdo arcticus	Species	Carcharhinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO173	Aconitum sajanense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO642	Artemisia bigelovii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16699	Agave utahensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16244	Clusia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO115	Eutreptia viridis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16775	Thermopsis lanceolata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO291	Suillus bovinus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3419	Quercus suber	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12409	Artemisia jacutica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11633	Kelletia kelletii	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19333	Byssothecium obiones	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1590	Sinningia aggregata	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15300	Bipolaris zeicola	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1934	Strychnos triplinervia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8829	Baccharis obtusifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1456	Bersama abyssinica	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25538	Senegalia pennata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11453	Centaurea cadmea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17226	Burkholderia pyrrocinia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9456	Rubus sanctus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13047	Epipolasis kushimotoensis	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6130	Mammillaria magnimamma	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11429	Matricaria parthenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27015	Valeriana hardwickii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10884	Glycyrrhiza squamulosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14435	Mnium hornum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6783	Avrainvillea rawsonii	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6756	Davallia orientalis	Species	Davalliaceae	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	4
Ki	1
Others	6

Activity Type	# Activity
Cell Line	4
Individual Protein	3
NON-MOLECULAR	1
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT326	Individual Protein	Squalene monooxygenase	Rattus norvegicus	IC50	=	1600.0	nM	PMID[456127]
NPT672	Cell Line	TE-671	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[456128]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[456128]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[456128]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[456128]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.74	ug ml-1	PMID[456128]
NPT1585	Organism	Microcystis aeruginosa	Microcystis aeruginosa	IC50	=	1600.0	nM	PMID[456129]
NPT1586	Organism	Anabaena flos-aquae	Dolichospermum flos-aquae	IC50	=	2800.0	nM	PMID[456129]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	17.2	%	PMID[456130]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	21.2	%	PMID[456130]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	35.7	%	PMID[456130]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	18.4	%	PMID[456130]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	51.3	%	PMID[456130]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	92.8	%	PMID[456130]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	3100.0	nM	PMID[456131]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Ki	=	6840.0	nM	PMID[456131]

☑ 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 NPC190204 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	1654
0.2-0.3	3563
0.3-0.4	8190
0.4-0.5	9501
0.5-0.6	5372
0.6-0.7	6455
0.7-0.8	6388
0.8-0.85	925
0.85-0.9	180
0.9-0.95	43
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC43918
1.0	High Similarity	NPC261411
0.9874	High Similarity	NPC47521
0.9873	High Similarity	NPC470271
0.9873	High Similarity	NPC311389
0.981	High Similarity	NPC175793
0.975	High Similarity	NPC470272
0.9625	High Similarity	NPC31034
0.962	High Similarity	NPC14030
0.962	High Similarity	NPC291957
0.956	High Similarity	NPC470898
0.9512	High Similarity	NPC472723
0.9458	High Similarity	NPC8940
0.943	High Similarity	NPC114791
0.943	High Similarity	NPC141331
0.943	High Similarity	NPC210501
0.943	High Similarity	NPC318826
0.943	High Similarity	NPC104222
0.9398	High Similarity	NPC80956
0.9383	High Similarity	NPC217781
0.9367	High Similarity	NPC172419
0.9367	High Similarity	NPC238419
0.9321	High Similarity	NPC142707
0.9321	High Similarity	NPC26536
0.9321	High Similarity	NPC49983
0.9321	High Similarity	NPC317671
0.9304	High Similarity	NPC239019
0.9304	High Similarity	NPC247629
0.9259	High Similarity	NPC162169
0.9259	High Similarity	NPC166851
0.9235	High Similarity	NPC260521
0.9235	High Similarity	NPC65489
0.9235	High Similarity	NPC469649
0.9231	High Similarity	NPC231254
0.9181	High Similarity	NPC240200
0.9181	High Similarity	NPC158214
0.9181	High Similarity	NPC290289
0.9181	High Similarity	NPC223534
0.9176	High Similarity	NPC469650
0.9176	High Similarity	NPC111490
0.9176	High Similarity	NPC261623
0.9162	High Similarity	NPC297574
0.9128	High Similarity	NPC187632
0.9128	High Similarity	NPC472720
0.9128	High Similarity	NPC31208
0.9128	High Similarity	NPC160543
0.9128	High Similarity	NPC472721
0.9128	High Similarity	NPC472724
0.9128	High Similarity	NPC93065
0.9128	High Similarity	NPC469652
0.9125	High Similarity	NPC474010
0.9125	High Similarity	NPC135222
0.9114	High Similarity	NPC61152
0.9114	High Similarity	NPC205037
0.9114	High Similarity	NPC44260
0.9114	High Similarity	NPC16024
0.9114	High Similarity	NPC3746
0.9075	High Similarity	NPC471091
0.9075	High Similarity	NPC40078
0.9075	High Similarity	NPC97924
0.907	High Similarity	NPC119094
0.907	High Similarity	NPC173872
0.907	High Similarity	NPC269046
0.9059	High Similarity	NPC123259
0.9059	High Similarity	NPC129533
0.9053	High Similarity	NPC198902
0.9017	High Similarity	NPC201814
0.9012	High Similarity	NPC237202
0.8976	High Similarity	NPC149300
0.8971	High Similarity	NPC476358
0.8966	High Similarity	NPC264302
0.8963	High Similarity	NPC469651
0.896	High Similarity	NPC477081
0.896	High Similarity	NPC7839
0.896	High Similarity	NPC477083
0.896	High Similarity	NPC142291
0.8929	High Similarity	NPC473550
0.8916	High Similarity	NPC473818
0.8889	High Similarity	NPC208797
0.8889	High Similarity	NPC53680
0.887	High Similarity	NPC3474
0.887	High Similarity	NPC189312
0.8869	High Similarity	NPC100251
0.8869	High Similarity	NPC65333
0.8868	High Similarity	NPC140151
0.8864	High Similarity	NPC477082
0.8862	High Similarity	NPC95421
0.8862	High Similarity	NPC198125
0.8861	High Similarity	NPC92117
0.8827	High Similarity	NPC134925
0.8824	High Similarity	NPC79736
0.8824	High Similarity	NPC67629
0.8817	High Similarity	NPC166674
0.8817	High Similarity	NPC98583
0.8817	High Similarity	NPC219600
0.8817	High Similarity	NPC34436
0.8817	High Similarity	NPC263119
0.8817	High Similarity	NPC46640
0.881	High Similarity	NPC181778
0.8797	High Similarity	NPC120621
0.8797	High Similarity	NPC248257
0.8797	High Similarity	NPC142528
0.8779	High Similarity	NPC125352
0.8772	High Similarity	NPC267549
0.8771	High Similarity	NPC174140
0.8765	High Similarity	NPC171706
0.8735	High Similarity	NPC121290
0.8728	High Similarity	NPC297503
0.8728	High Similarity	NPC97119
0.8728	High Similarity	NPC135831
0.8721	High Similarity	NPC472725
0.8721	High Similarity	NPC472726
0.8712	High Similarity	NPC300845
0.8712	High Similarity	NPC104983
0.8712	High Similarity	NPC88803
0.8712	High Similarity	NPC250436
0.8712	High Similarity	NPC291948
0.8686	High Similarity	NPC105591
0.8667	High Similarity	NPC24627
0.8667	High Similarity	NPC289346
0.8659	High Similarity	NPC38779
0.8659	High Similarity	NPC257309
0.8659	High Similarity	NPC114179
0.8659	High Similarity	NPC68324
0.8659	High Similarity	NPC289322
0.8659	High Similarity	NPC160512
0.8659	High Similarity	NPC156818
0.865	High Similarity	NPC472835
0.865	High Similarity	NPC203757
0.8647	High Similarity	NPC67134
0.8647	High Similarity	NPC47140
0.8639	High Similarity	NPC197708
0.8639	High Similarity	NPC658
0.8634	High Similarity	NPC252979
0.8629	High Similarity	NPC112380
0.8621	High Similarity	NPC132111
0.8616	High Similarity	NPC268366
0.8614	High Similarity	NPC266365
0.8613	High Similarity	NPC471030
0.8608	High Similarity	NPC108455
0.8606	High Similarity	NPC87317
0.8605	High Similarity	NPC473713
0.8598	High Similarity	NPC318432
0.8596	High Similarity	NPC88560
0.8596	High Similarity	NPC175230
0.8596	High Similarity	NPC172033
0.8588	High Similarity	NPC204937
0.8588	High Similarity	NPC149011
0.858	High Similarity	NPC179947
0.858	High Similarity	NPC311912
0.858	High Similarity	NPC269625
0.858	High Similarity	NPC475179
0.8563	High Similarity	NPC90905
0.8563	High Similarity	NPC285108
0.8563	High Similarity	NPC4013
0.8563	High Similarity	NPC33298
0.8563	High Similarity	NPC170203
0.8563	High Similarity	NPC469371
0.8555	High Similarity	NPC253521
0.8555	High Similarity	NPC476618
0.8555	High Similarity	NPC267680
0.8555	High Similarity	NPC476619
0.8555	High Similarity	NPC196127
0.8555	High Similarity	NPC476622
0.8555	High Similarity	NPC293626
0.8555	High Similarity	NPC476620
0.8555	High Similarity	NPC476621
0.8555	High Similarity	NPC37668
0.8555	High Similarity	NPC217387
0.8555	High Similarity	NPC476623
0.8555	High Similarity	NPC258044
0.8555	High Similarity	NPC113836
0.8554	High Similarity	NPC24164
0.8554	High Similarity	NPC53889
0.8545	High Similarity	NPC472860
0.8544	High Similarity	NPC226738
0.8544	High Similarity	NPC190587
0.8544	High Similarity	NPC229036
0.8544	High Similarity	NPC22176
0.8544	High Similarity	NPC121573
0.8538	High Similarity	NPC5786
0.8538	High Similarity	NPC102851
0.8538	High Similarity	NPC38438
0.8537	High Similarity	NPC156624
0.8537	High Similarity	NPC172920
0.8531	High Similarity	NPC473618
0.8529	High Similarity	NPC88557
0.8523	High Similarity	NPC473686
0.8523	High Similarity	NPC229817
0.8523	High Similarity	NPC475352
0.8523	High Similarity	NPC474093
0.8523	High Similarity	NPC475220
0.8523	High Similarity	NPC221140
0.8523	High Similarity	NPC104910
0.8514	High Similarity	NPC475662
0.8514	High Similarity	NPC293227
0.8514	High Similarity	NPC473631
0.8514	High Similarity	NPC473717
0.8509	High Similarity	NPC75945
0.8497	Intermediate Similarity	NPC61904

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 NPC190204 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	928
0.2-0.3	1824
0.3-0.4	2780
0.4-0.5	1906
0.5-0.6	968
0.6-0.7	254
0.7-0.8	120
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8712	High Similarity	NPD4868	Clinical (unspecified phase)
0.8647	High Similarity	NPD7993	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD1465	Phase 2
0.8182	Intermediate Similarity	NPD8313	Approved
0.8182	Intermediate Similarity	NPD8312	Approved
0.8161	Intermediate Similarity	NPD7074	Phase 3
0.8161	Intermediate Similarity	NPD7472	Approved
0.815	Intermediate Similarity	NPD7228	Approved
0.815	Intermediate Similarity	NPD3818	Discontinued
0.8125	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD6797	Phase 2
0.8103	Intermediate Similarity	NPD7054	Approved
0.8103	Intermediate Similarity	NPD5844	Phase 1
0.8095	Intermediate Similarity	NPD8151	Discontinued
0.8068	Intermediate Similarity	NPD7251	Discontinued
0.8059	Intermediate Similarity	NPD6234	Discontinued
0.8023	Intermediate Similarity	NPD7808	Phase 3
0.8023	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6166	Phase 2
0.7931	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD8455	Phase 2
0.7911	Intermediate Similarity	NPD230	Phase 1
0.7886	Intermediate Similarity	NPD7473	Discontinued
0.787	Intermediate Similarity	NPD37	Approved
0.7861	Intermediate Similarity	NPD6959	Discontinued
0.7836	Intermediate Similarity	NPD4965	Approved
0.7836	Intermediate Similarity	NPD4967	Phase 2
0.7836	Intermediate Similarity	NPD4966	Approved
0.7805	Intermediate Similarity	NPD6190	Approved
0.779	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7266	Discontinued
0.7765	Intermediate Similarity	NPD1934	Approved
0.7765	Intermediate Similarity	NPD7685	Pre-registration
0.7765	Intermediate Similarity	NPD7240	Approved
0.7759	Intermediate Similarity	NPD7199	Phase 2
0.7727	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7390	Discontinued
0.7697	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6559	Discontinued
0.7647	Intermediate Similarity	NPD4380	Phase 2
0.7616	Intermediate Similarity	NPD7819	Suspended
0.7586	Intermediate Similarity	NPD3749	Approved
0.756	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD3751	Discontinued
0.7529	Intermediate Similarity	NPD7768	Phase 2
0.7529	Intermediate Similarity	NPD1653	Approved
0.7514	Intermediate Similarity	NPD2801	Approved
0.7514	Intermediate Similarity	NPD3787	Discontinued
0.7513	Intermediate Similarity	NPD8319	Approved
0.7513	Intermediate Similarity	NPD8320	Phase 1
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6535	Approved
0.75	Intermediate Similarity	NPD6534	Approved
0.7486	Intermediate Similarity	NPD7075	Discontinued
0.7474	Intermediate Similarity	NPD7700	Phase 2
0.7474	Intermediate Similarity	NPD7699	Phase 2
0.7471	Intermediate Similarity	NPD3817	Phase 2
0.7461	Intermediate Similarity	NPD7435	Discontinued
0.7459	Intermediate Similarity	NPD8150	Discontinued
0.7429	Intermediate Similarity	NPD3882	Suspended
0.7425	Intermediate Similarity	NPD3750	Approved
0.7425	Intermediate Similarity	NPD8166	Discontinued
0.7423	Intermediate Similarity	NPD7871	Phase 2
0.7423	Intermediate Similarity	NPD7870	Phase 2
0.7407	Intermediate Similarity	NPD943	Approved
0.7399	Intermediate Similarity	NPD7411	Suspended
0.7396	Intermediate Similarity	NPD6781	Approved
0.7396	Intermediate Similarity	NPD6778	Approved
0.7396	Intermediate Similarity	NPD6779	Approved
0.7396	Intermediate Similarity	NPD1511	Approved
0.7396	Intermediate Similarity	NPD6780	Approved
0.7396	Intermediate Similarity	NPD6777	Approved
0.7396	Intermediate Similarity	NPD6782	Approved
0.7396	Intermediate Similarity	NPD6776	Approved
0.7394	Intermediate Similarity	NPD5405	Approved
0.7394	Intermediate Similarity	NPD5406	Approved
0.7394	Intermediate Similarity	NPD5408	Approved
0.7394	Intermediate Similarity	NPD5404	Approved
0.7391	Intermediate Similarity	NPD3764	Approved
0.7384	Intermediate Similarity	NPD7458	Discontinued
0.7374	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7783	Phase 2
0.7371	Intermediate Similarity	NPD7680	Approved
0.7371	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD9269	Phase 2
0.7323	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7874	Approved
0.7314	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1512	Approved
0.7305	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5494	Approved
0.7282	Intermediate Similarity	NPD7696	Phase 3
0.7282	Intermediate Similarity	NPD7698	Approved
0.7282	Intermediate Similarity	NPD7697	Approved
0.7273	Intermediate Similarity	NPD5402	Approved
0.7263	Intermediate Similarity	NPD6213	Phase 3
0.7263	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6212	Phase 3
0.7251	Intermediate Similarity	NPD2533	Approved
0.7251	Intermediate Similarity	NPD2532	Approved
0.7251	Intermediate Similarity	NPD2534	Approved
0.7229	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7701	Phase 2
0.7202	Intermediate Similarity	NPD1549	Phase 2
0.7184	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6801	Discontinued
0.7151	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6823	Phase 2
0.7143	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3748	Approved
0.7126	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1510	Phase 2
0.7118	Intermediate Similarity	NPD4628	Phase 3
0.7118	Intermediate Similarity	NPD7003	Approved
0.7114	Intermediate Similarity	NPD7801	Approved
0.7093	Intermediate Similarity	NPD6799	Approved
0.7091	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1613	Approved
0.7074	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD9268	Approved
0.7069	Intermediate Similarity	NPD5403	Approved
0.7059	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6599	Discontinued
0.7035	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5401	Approved
0.6954	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7229	Phase 3
0.6919	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3027	Phase 3
0.6902	Remote Similarity	NPD5242	Approved
0.6902	Remote Similarity	NPD3926	Phase 2
0.6893	Remote Similarity	NPD3226	Approved
0.6889	Remote Similarity	NPD5353	Approved
0.6886	Remote Similarity	NPD1240	Approved
0.6885	Remote Similarity	NPD8127	Discontinued
0.6882	Remote Similarity	NPD2935	Discontinued
0.6882	Remote Similarity	NPD2796	Approved
0.6882	Remote Similarity	NPD7177	Discontinued
0.6867	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6674	Discontinued
0.6848	Remote Similarity	NPD5710	Approved
0.6848	Remote Similarity	NPD5711	Approved
0.6823	Remote Similarity	NPD8434	Phase 2
0.6821	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD1607	Approved
0.6798	Remote Similarity	NPD7585	Approved
0.6798	Remote Similarity	NPD3455	Phase 2
0.6792	Remote Similarity	NPD9545	Approved
0.6784	Remote Similarity	NPD1551	Phase 2
0.6776	Remote Similarity	NPD919	Approved
0.6765	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7930	Approved
0.6753	Remote Similarity	NPD4287	Approved
0.6749	Remote Similarity	NPD7583	Approved
0.6747	Remote Similarity	NPD4908	Phase 1
0.6746	Remote Similarity	NPD1933	Approved
0.6723	Remote Similarity	NPD6273	Approved
0.6717	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5006	Approved
0.6716	Remote Similarity	NPD5005	Approved
0.6707	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4288	Approved
0.6702	Remote Similarity	NPD7549	Discontinued
0.67	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD9494	Approved
0.6686	Remote Similarity	NPD6099	Approved
0.6686	Remote Similarity	NPD6100	Approved
0.6667	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7584	Approved
0.6667	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1470	Approved
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD8059	Phase 3
0.6651	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD447	Suspended
0.6647	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2346	Discontinued
0.663	Remote Similarity	NPD6386	Approved
0.663	Remote Similarity	NPD6385	Approved
0.6618	Remote Similarity	NPD7999	Approved
0.6614	Remote Similarity	NPD7799	Discontinued
0.6613	Remote Similarity	NPD1247	Approved
0.66	Remote Similarity	NPD4420	Approved
0.6597	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