NPASS Compound

Structure

CID119094 OpenBabel06191715472D 68 75 0 0 1 0 0 0 0 0999 V2000 -3.4077 0.9837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5558 2.4593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9684 -1.9114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7317 0.7236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3275 2.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0799 0.3427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1155 -1.0474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5558 1.4756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7973 -1.3207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2714 0.3159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3275 2.3275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1795 0.8519 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2597 1.4756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4077 2.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5655 -2.0585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3149 0.5289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8676 3.2630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8519 -0.4919 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7755 1.0383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2233 -0.8772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3944 -0.2866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1795 1.4756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8676 2.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2597 2.4593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9914 -1.6150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4379 -0.0736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4077 2.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8203 -1.0244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9776 -0.4813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6713 1.3438 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7039 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4077 2.3275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7039 0.9837 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8519 1.4756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7039 0.9837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2141 -1.5154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8825 0.7922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7039 2.3275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8676 0.3118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0314 1.7039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9837 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1116 0.9837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4077 3.9349 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8391 -3.0034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0512 1.1812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8676 4.2467 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7257 0.7837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5209 1.9885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1116 2.9512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9466 -1.8505 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3710 -0.3851 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2597 3.4430 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5018 -0.3149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1744 -1.4452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9259 0.3936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7039 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2932 -2.4960 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4735 1.5786 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4493 3.2777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5632 -0.3838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9816 1.4493 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6071 -1.4168 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 2.3275 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8996 2.1957 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3168 1.0332 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1638 2.0157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8519 1.4756 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 19 1 0 0 0 0 7 62 1 0 0 0 0 8 35 1 0 0 0 0 9 20 1 0 0 0 0 9 36 1 0 0 0 0 10 21 1 0 0 0 0 10 37 1 0 0 0 0 11 23 1 0 0 0 0 11 38 1 0 0 0 0 12 6 1 6 0 0 0 12 22 1 0 0 0 0 12 39 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 7 1 1 0 0 0 18 31 1 0 0 0 0 18 63 1 0 0 0 0 19 47 2 0 0 0 0 19 48 1 0 0 0 0 20 21 1 0 0 0 0 20 28 2 0 0 0 0 21 29 2 0 0 0 0 22 23 1 1 0 0 0 22 30 1 0 0 0 0 23 32 2 0 0 0 0 24 49 1 0 0 0 0 25 28 1 0 0 0 0 25 50 1 0 0 0 0 26 29 1 0 0 0 0 26 51 1 0 0 0 0 27 32 1 0 0 0 0 27 52 1 0 0 0 0 28 53 1 0 0 0 0 29 54 1 0 0 0 0 30 40 1 0 0 0 0 30 55 1 1 0 0 0 31 33 1 0 0 0 0 31 64 1 6 0 0 0 32 65 1 0 0 0 0 33 34 1 0 0 0 0 33 66 1 1 0 0 0 34 41 1 0 0 0 0 34 67 1 6 0 0 0 35 56 2 0 0 0 0 35 68 1 0 0 0 0 36 57 2 0 0 0 0 36 62 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 64 1 0 0 0 0 40 61 2 0 0 0 0 40 65 1 0 0 0 0 41 63 1 0 0 0 0 41 68 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	954.1
Volume:	836.484
LogP:	1.058
LogD:	0.39
LogS:	-3.938
# Rotatable Bonds:	5
TPSA:	454.16
# H-Bond Aceptor:	27
# H-Bond Donor:	14
# Rings:	8
# Heavy Atoms:	27

MedChem Properties

QED Drug-Likeness Score:	0.051
Synthetic Accessibility Score:	7.315
Fsp3:	0.22
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-7.027
MDCK Permeability:	6.609135652979603e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.991
20% Bioavailability (F20%):	0.88
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	84.3093032836914%
Volume Distribution (VD):	0.48
Pgp-substrate:	50.962303161621094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.017
CYP2C9-inhibitor:	0.394
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	6.068
Half-life (T1/2):	0.981

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.578
Drug-inuced Liver Injury (DILI):	0.998
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.185
Skin Sensitization:	0.94
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.903
Respiratory Toxicity:	0.003

Download Data

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

Natural Product: NPC119094

Natural Product ID:	NPC119094
*Common Name:**	Chebulagic Acid
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HGJXAVROWQLCTP-YABCKIEDSA-N
Standard InCHI:	InChI=1S/C41H30O27/c42-13-1-8(2-14(43)24(13)49)35(56)68-41-34-33-31(64-39(60)12(6-19(47)48)22-23-11(38(59)67-34)5-17(46)27(52)32(23)65-40(61)30(22)55)18(63-41)7-62-36(57)9-3-15(44)25(50)28(53)20(9)21-10(37(58)66-33)4-16(45)26(51)29(21)54/h1-5,12,18,22,30-31,33-34,41-46,49-55H,6-7H2,(H,47,48)/t12-,18+,22-,30-,31+,33-,34+,41-/m0/s1
SMILES:	OC(=O)C[C@@H]1C(=O)O[C@@H]2[C@H]3COC(=O)c4cc(O)c(c(c4c4c(C(=O)O[C@@H]2[C@@H](OC(=O)c2c5[C@H]1[C@H](O)C(=O)Oc5c(c(c2)O)O)[C@@H](O3)OC(=O)c1cc(O)c(c(c1)O)O)cc(O)c(c4O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL525240
PubChem CID:	442674
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
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754604]
NPO28847	Plectranthus fruticosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713399]
NPO28847	Plectranthus fruticosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104491]
NPO27007	Cunonia macrophylla	Species	Cunoniaceae	Eukaryota	n.a.	New Caledonia	n.a.	PMID[15652581]
NPO28785	Lumbricus terrestris	Species	Lumbricidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1909513]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	Roots	Simao city, Yunnan Province, China	2007-MAY	PMID[19374435]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21190854]
NPO25909	Leonurus sibiricus	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21375312]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	stems and twigs	Beihai, Guangxi province, China	2008-Jan	PMID[22196120]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	roots	n.a.	n.a.	PMID[26259802]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	twig	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	bark	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[7623051]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29030	Zanthoxylum americanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7690	Nyssa sinensis	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27007	Cunonia macrophylla	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25909	Leonurus sibiricus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7690	Nyssa sinensis	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27007	Cunonia macrophylla	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29030	Zanthoxylum americanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25909	Leonurus sibiricus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29030	Zanthoxylum americanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25909	Leonurus sibiricus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29030	Zanthoxylum americanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	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]
NPO22244	Terminalia bellirica	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7862	Faramea cyanea	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27007	Cunonia macrophylla	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1496	Stevia porphyrea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8313	Rhipocephalus phoenix	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1290	Trilisa odoratissima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29030	Zanthoxylum americanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29145	Carya tonkinensis	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2922	Botryosphaeria berengeriana	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28785	Lumbricus terrestris	Species	Lumbricidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29452	Plantago indica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7690	Nyssa sinensis	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28867	Holocarpha obconica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28924	Spongilla lacustris	Species	Spongillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9757	Cladonia macilenta	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28828	Rana arvalis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25909	Leonurus sibiricus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6382	Chlorocebus aethiops	Species	Cercopithecidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7292	Excoecaria kawakamii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8848	Colubrina elliptica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2461	Perilla acuta	Species	Araneidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29533	Argusia argentea	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28847	Plectranthus fruticosus	Species	Lamiaceae	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
EC50	1
ED50	5
IC50	12
Others	18

Activity Type	# Activity
Cell Line	4
Individual Protein	3
NON-MOLECULAR	1
Organism	11
Others	16
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT326	Individual Protein	Squalene monooxygenase	Rattus norvegicus	IC50	=	3200.0	nM	PMID[564707]
NPT672	Cell Line	TE-671	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[564708]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[564708]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[564708]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[564708]
NPT143	Individual Protein	DNA topoisomerase I	Homo sapiens	IC50	=	50.0	nM	PMID[564709]
NPT143	Individual Protein	DNA topoisomerase I	Homo sapiens	IC50	=	100.0	nM	PMID[564709]
NPT316	Protein Family	Protein kinase C (PKC)	Homo sapiens	IC50	=	30000.0	nM	PMID[564702]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	>	50.0	%	PMID[564703]
NPT2	Others	Unspecified		IC50	>	50.0	ug.mL-1	PMID[564705]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	50.0	ug.mL-1	PMID[564705]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	>	50.0	ug.mL-1	PMID[564705]
NPT2	Others	Unspecified		IC50	>	50.0	ug.mL-1	PMID[564706]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	50.0	ug.mL-1	PMID[564706]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	>	50.0	ug.mL-1	PMID[564706]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.8	ug ml-1	PMID[564708]
NPT2	Others	Unspecified		Activity	=	67.0	%	PMID[564710]
NPT2	Others	Unspecified		Activity	=	94.0	%	PMID[564710]
NPT2	Others	Unspecified		Activity	=	6.0	%	PMID[564710]
NPT2	Others	Unspecified		Activity	=	31.0	%	PMID[564710]
NPT2	Others	Unspecified		Activity	=	48.0	%	PMID[564710]
NPT2	Others	Unspecified		Activity	=	90.0	%	PMID[564710]
NPT2	Others	Unspecified		Activity	=	106.0	%	PMID[564710]
NPT2	Others	Unspecified		Activity	=	74.0	%	PMID[564710]
NPT2	Others	Unspecified		Activity	=	68.0	%	PMID[564710]
NPT2	Others	Unspecified		Activity	=	8.0	%	PMID[564710]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-6.5	mmHg	PMID[564711]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	4.7	n.a.	PMID[564712]
NPT27	Others	Unspecified		CC50	=	104910.0	nM	PMID[564712]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	EC50	=	22250.0	nM	PMID[564712]
NPT2	Others	Unspecified		IC50	=	9030.0	nM	PMID[564712]
NPT2	Others	Unspecified		IC50	=	48000.0	nM	PMID[564713]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	12.0	mm	PMID[564713]
NPT1285	Organism	Corynebacterium accolens	Corynebacterium accolens	IZ	=	10.0	mm	PMID[564713]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	11.0	mm	PMID[564713]
NPT1286	Organism	Pectobacterium carotovorum	Pectobacterium carotovorum	IZ	=	19.0	mm	PMID[564713]

☑ 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 NPC119094 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	456
0.1-0.2	1892
0.2-0.3	4142
0.3-0.4	9364
0.4-0.5	8887
0.5-0.6	4712
0.6-0.7	6444
0.7-0.8	5514
0.8-0.85	943
0.85-0.9	269
0.9-0.95	70
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC173872
0.9884	High Similarity	NPC7839
0.9884	High Similarity	NPC142291
0.9649	High Similarity	NPC80956
0.9532	High Similarity	NPC297574
0.9489	High Similarity	NPC201814
0.9425	High Similarity	NPC123259
0.9425	High Similarity	NPC129533
0.9419	High Similarity	NPC472723
0.9322	High Similarity	NPC269046
0.9322	High Similarity	NPC477083
0.9322	High Similarity	NPC477081
0.9318	High Similarity	NPC261623
0.9318	High Similarity	NPC111490
0.927	High Similarity	NPC472721
0.927	High Similarity	NPC31208
0.927	High Similarity	NPC160543
0.927	High Similarity	NPC93065
0.927	High Similarity	NPC472720
0.927	High Similarity	NPC469652
0.927	High Similarity	NPC472724
0.9266	High Similarity	NPC237202
0.9261	High Similarity	NPC231254
0.9257	High Similarity	NPC8940
0.9227	High Similarity	NPC3474
0.9222	High Similarity	NPC477082
0.9213	High Similarity	NPC240200
0.9213	High Similarity	NPC158214
0.9213	High Similarity	NPC223534
0.9213	High Similarity	NPC290289
0.9209	High Similarity	NPC469650
0.9195	High Similarity	NPC473713
0.9191	High Similarity	NPC219600
0.9191	High Similarity	NPC34436
0.9191	High Similarity	NPC263119
0.9191	High Similarity	NPC166674
0.9191	High Similarity	NPC473550
0.9191	High Similarity	NPC46640
0.9186	High Similarity	NPC181778
0.9186	High Similarity	NPC470272
0.9181	High Similarity	NPC311389
0.9181	High Similarity	NPC470271
0.9162	High Similarity	NPC187632
0.9157	High Similarity	NPC65489
0.9157	High Similarity	NPC469649
0.9157	High Similarity	NPC260521
0.9148	High Similarity	NPC208797
0.9148	High Similarity	NPC53680
0.9123	High Similarity	NPC175793
0.9116	High Similarity	NPC476358
0.9111	High Similarity	NPC97924
0.9111	High Similarity	NPC471091
0.9111	High Similarity	NPC264302
0.9111	High Similarity	NPC40078
0.907	High Similarity	NPC43918
0.907	High Similarity	NPC261411
0.907	High Similarity	NPC473818
0.907	High Similarity	NPC190204
0.904	High Similarity	NPC170203
0.904	High Similarity	NPC125352
0.9023	High Similarity	NPC65333
0.9017	High Similarity	NPC149300
0.9016	High Similarity	NPC189312
0.8989	High Similarity	NPC135831
0.8989	High Similarity	NPC297503
0.8989	High Similarity	NPC97119
0.8983	High Similarity	NPC198902
0.8977	High Similarity	NPC67629
0.8977	High Similarity	NPC79736
0.8966	High Similarity	NPC47521
0.896	High Similarity	NPC31034
0.8947	High Similarity	NPC291957
0.8947	High Similarity	NPC14030
0.8944	High Similarity	NPC475360
0.8927	High Similarity	NPC267549
0.8914	High Similarity	NPC38438
0.8914	High Similarity	NPC100251
0.8908	High Similarity	NPC198125
0.8908	High Similarity	NPC197708
0.8908	High Similarity	NPC658
0.8908	High Similarity	NPC95421
0.8895	High Similarity	NPC121290
0.8895	High Similarity	NPC470898
0.8889	High Similarity	NPC474093
0.8889	High Similarity	NPC104910
0.8883	High Similarity	NPC132111
0.8883	High Similarity	NPC470718
0.8871	High Similarity	NPC470450
0.8864	High Similarity	NPC98583
0.884	High Similarity	NPC97817
0.884	High Similarity	NPC269625
0.884	High Similarity	NPC179947
0.884	High Similarity	NPC475179
0.884	High Similarity	NPC72554
0.884	High Similarity	NPC30011
0.884	High Similarity	NPC105591
0.8833	High Similarity	NPC470713
0.8833	High Similarity	NPC25946
0.8833	High Similarity	NPC470720
0.8833	High Similarity	NPC460984
0.8833	High Similarity	NPC21359
0.8833	High Similarity	NPC470717
0.882	High Similarity	NPC113836
0.882	High Similarity	NPC476620
0.882	High Similarity	NPC476622
0.882	High Similarity	NPC37668
0.882	High Similarity	NPC476618
0.882	High Similarity	NPC476623
0.882	High Similarity	NPC476619
0.882	High Similarity	NPC253521
0.882	High Similarity	NPC258044
0.882	High Similarity	NPC267680
0.882	High Similarity	NPC217387
0.882	High Similarity	NPC196127
0.882	High Similarity	NPC293626
0.882	High Similarity	NPC476621
0.8817	High Similarity	NPC174140
0.8814	High Similarity	NPC473630
0.8807	High Similarity	NPC47140
0.8807	High Similarity	NPC102851
0.8807	High Similarity	NPC5786
0.8807	High Similarity	NPC67134
0.8791	High Similarity	NPC473618
0.8791	High Similarity	NPC205721
0.8785	High Similarity	NPC473554
0.8785	High Similarity	NPC295625
0.8785	High Similarity	NPC112380
0.8785	High Similarity	NPC470719
0.8778	High Similarity	NPC241781
0.8778	High Similarity	NPC156785
0.8778	High Similarity	NPC162394
0.8771	High Similarity	NPC471030
0.8771	High Similarity	NPC472726
0.8771	High Similarity	NPC472725
0.8764	High Similarity	NPC144097
0.8764	High Similarity	NPC61904
0.8757	High Similarity	NPC175230
0.8757	High Similarity	NPC88560
0.8757	High Similarity	NPC163165
0.8757	High Similarity	NPC172033
0.875	High Similarity	NPC204937
0.875	High Similarity	NPC149011
0.8729	High Similarity	NPC249560
0.8729	High Similarity	NPC223860
0.8729	High Similarity	NPC470416
0.8729	High Similarity	NPC49690
0.8729	High Similarity	NPC275977
0.8729	High Similarity	NPC318119
0.8728	High Similarity	NPC285108
0.8728	High Similarity	NPC33298
0.8722	High Similarity	NPC117668
0.8722	High Similarity	NPC469371
0.8721	High Similarity	NPC289346
0.8721	High Similarity	NPC24627
0.8721	High Similarity	NPC24164
0.8715	High Similarity	NPC477895
0.8715	High Similarity	NPC217520
0.8715	High Similarity	NPC35167
0.8715	High Similarity	NPC472387
0.8715	High Similarity	NPC139571
0.8713	High Similarity	NPC238419
0.8713	High Similarity	NPC172419
0.8708	High Similarity	NPC34267
0.8708	High Similarity	NPC81042
0.8708	High Similarity	NPC253685
0.8708	High Similarity	NPC214621
0.8708	High Similarity	NPC171706
0.8708	High Similarity	NPC223426
0.8681	High Similarity	NPC221140
0.8681	High Similarity	NPC473686
0.8681	High Similarity	NPC475352
0.8681	High Similarity	NPC475220
0.8681	High Similarity	NPC33083
0.8681	High Similarity	NPC87583
0.8681	High Similarity	NPC229817
0.8678	High Similarity	NPC67959
0.8674	High Similarity	NPC36138
0.8674	High Similarity	NPC321916
0.8667	High Similarity	NPC212290
0.8663	High Similarity	NPC37502
0.8663	High Similarity	NPC87317
0.8663	High Similarity	NPC40702
0.8663	High Similarity	NPC267627
0.8659	High Similarity	NPC268533
0.8659	High Similarity	NPC472992
0.8659	High Similarity	NPC472991
0.8655	High Similarity	NPC239019
0.8655	High Similarity	NPC104983
0.8655	High Similarity	NPC300845
0.8655	High Similarity	NPC247629
0.8655	High Similarity	NPC250436
0.8655	High Similarity	NPC318432
0.8655	High Similarity	NPC291948
0.8655	High Similarity	NPC88803
0.8652	High Similarity	NPC316539
0.8652	High Similarity	NPC472993
0.8644	High Similarity	NPC52598
0.8644	High Similarity	NPC285197
0.8636	High Similarity	NPC298847
0.8636	High Similarity	NPC45400

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 NPC119094 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	985
0.2-0.3	2116
0.3-0.4	2676
0.4-0.5	1785
0.5-0.6	795
0.6-0.7	285
0.7-0.8	95
0.8-0.85	18
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9023	High Similarity	NPD7993	Clinical (unspecified phase)
0.8655	High Similarity	NPD4868	Clinical (unspecified phase)
0.8538	High Similarity	NPD1465	Phase 2
0.85	High Similarity	NPD4338	Clinical (unspecified phase)
0.85	High Similarity	NPD7808	Phase 3
0.8492	Intermediate Similarity	NPD6797	Phase 2
0.8444	Intermediate Similarity	NPD7251	Discontinued
0.8436	Intermediate Similarity	NPD7074	Phase 3
0.8436	Intermediate Similarity	NPD7472	Approved
0.8418	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD6166	Phase 2
0.8418	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD7054	Approved
0.838	Intermediate Similarity	NPD5844	Phase 1
0.8352	Intermediate Similarity	NPD8313	Approved
0.8352	Intermediate Similarity	NPD8312	Approved
0.8324	Intermediate Similarity	NPD7228	Approved
0.8324	Intermediate Similarity	NPD3818	Discontinued
0.8138	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8128	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD8455	Phase 2
0.8079	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD8151	Discontinued
0.8056	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD7199	Phase 2
0.8034	Intermediate Similarity	NPD6234	Discontinued
0.8	Intermediate Similarity	NPD6232	Discontinued
0.7968	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD7473	Discontinued
0.7955	Intermediate Similarity	NPD37	Approved
0.7946	Intermediate Similarity	NPD7240	Approved
0.7944	Intermediate Similarity	NPD6959	Discontinued
0.7923	Intermediate Similarity	NPD3751	Discontinued
0.7921	Intermediate Similarity	NPD4966	Approved
0.7921	Intermediate Similarity	NPD4965	Approved
0.7921	Intermediate Similarity	NPD4967	Phase 2
0.7853	Intermediate Similarity	NPD1934	Approved
0.7849	Intermediate Similarity	NPD7685	Pre-registration
0.7829	Intermediate Similarity	NPD1653	Approved
0.7814	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD3787	Discontinued
0.7765	Intermediate Similarity	NPD3817	Phase 2
0.7754	Intermediate Similarity	NPD6559	Discontinued
0.7722	Intermediate Similarity	NPD3882	Suspended
0.7709	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD3749	Approved
0.768	Intermediate Similarity	NPD7075	Discontinued
0.767	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD7435	Discontinued
0.7635	Intermediate Similarity	NPD7783	Phase 2
0.7635	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD7819	Suspended
0.7611	Intermediate Similarity	NPD2801	Approved
0.7596	Intermediate Similarity	NPD5494	Approved
0.7576	Intermediate Similarity	NPD6779	Approved
0.7576	Intermediate Similarity	NPD6781	Approved
0.7576	Intermediate Similarity	NPD6778	Approved
0.7576	Intermediate Similarity	NPD6782	Approved
0.7576	Intermediate Similarity	NPD6777	Approved
0.7576	Intermediate Similarity	NPD6780	Approved
0.7576	Intermediate Similarity	NPD6776	Approved
0.7569	Intermediate Similarity	NPD5402	Approved
0.7569	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7697	Approved
0.755	Intermediate Similarity	NPD7680	Approved
0.755	Intermediate Similarity	NPD7698	Approved
0.755	Intermediate Similarity	NPD7696	Phase 3
0.7542	Intermediate Similarity	NPD4380	Phase 2
0.7527	Intermediate Similarity	NPD7768	Phase 2
0.7525	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD1512	Approved
0.7514	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD8320	Phase 1
0.7512	Intermediate Similarity	NPD7871	Phase 2
0.7512	Intermediate Similarity	NPD8319	Approved
0.7512	Intermediate Similarity	NPD7870	Phase 2
0.75	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7874	Approved
0.7488	Intermediate Similarity	NPD7701	Phase 2
0.7486	Intermediate Similarity	NPD6190	Approved
0.7459	Intermediate Similarity	NPD6801	Discontinued
0.7429	Intermediate Similarity	NPD3750	Approved
0.7401	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD1511	Approved
0.7389	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD7699	Phase 2
0.7387	Intermediate Similarity	NPD7700	Phase 2
0.7379	Intermediate Similarity	NPD7801	Approved
0.7374	Intermediate Similarity	NPD5403	Approved
0.7371	Intermediate Similarity	NPD8434	Phase 2
0.736	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7266	Discontinued
0.7323	Intermediate Similarity	NPD6534	Approved
0.7323	Intermediate Similarity	NPD6535	Approved
0.7303	Intermediate Similarity	NPD6799	Approved
0.7287	Intermediate Similarity	NPD3926	Phase 2
0.7282	Intermediate Similarity	NPD8150	Discontinued
0.7273	Intermediate Similarity	NPD8127	Discontinued
0.7267	Intermediate Similarity	NPD230	Phase 1
0.7263	Intermediate Similarity	NPD5401	Approved
0.7253	Intermediate Similarity	NPD6599	Discontinued
0.7232	Intermediate Similarity	NPD4628	Phase 3
0.723	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD1549	Phase 2
0.7209	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1613	Approved
0.7198	Intermediate Similarity	NPD3226	Approved
0.7198	Intermediate Similarity	NPD7458	Discontinued
0.7175	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD6674	Discontinued
0.7167	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD919	Approved
0.7163	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3748	Approved
0.7092	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6823	Phase 2
0.7072	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD2534	Approved
0.7072	Intermediate Similarity	NPD2533	Approved
0.7072	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD2532	Approved
0.7053	Intermediate Similarity	NPD7229	Phase 3
0.7033	Intermediate Similarity	NPD6273	Approved
0.7018	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7390	Discontinued
0.7	Intermediate Similarity	NPD1247	Approved
0.6995	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7549	Discontinued
0.6986	Remote Similarity	NPD7585	Approved
0.6977	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD1510	Phase 2
0.6944	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7003	Approved
0.6944	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD7583	Approved
0.6936	Remote Similarity	NPD3027	Phase 3
0.6931	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6213	Phase 3
0.6931	Remote Similarity	NPD6212	Phase 3
0.6915	Remote Similarity	NPD5353	Approved
0.691	Remote Similarity	NPD2796	Approved
0.6907	Remote Similarity	NPD7177	Discontinued
0.6897	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6798	Discontinued
0.6893	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7097	Phase 1
0.6879	Remote Similarity	NPD4908	Phase 1
0.6875	Remote Similarity	NPD1933	Approved
0.6875	Remote Similarity	NPD447	Suspended
0.6866	Remote Similarity	NPD4287	Approved
0.6854	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD8166	Discontinued
0.6839	Remote Similarity	NPD5242	Approved
0.6818	Remote Similarity	NPD943	Approved
0.6818	Remote Similarity	NPD4060	Phase 1
0.6816	Remote Similarity	NPD5408	Approved
0.6816	Remote Similarity	NPD5405	Approved
0.6816	Remote Similarity	NPD1551	Phase 2
0.6816	Remote Similarity	NPD6099	Approved
0.6816	Remote Similarity	NPD5404	Approved
0.6816	Remote Similarity	NPD6100	Approved
0.6816	Remote Similarity	NPD5406	Approved
0.681	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3764	Approved
0.68	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7930	Approved
0.678	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6355	Discontinued
0.6777	Remote Similarity	NPD7584	Approved
0.6768	Remote Similarity	NPD7039	Approved
0.6768	Remote Similarity	NPD7038	Approved
0.6761	Remote Similarity	NPD6233	Phase 2
0.6737	Remote Similarity	NPD4288	Approved
0.6733	Remote Similarity	NPD6841	Approved
0.6733	Remote Similarity	NPD6842	Approved
0.6733	Remote Similarity	NPD6843	Phase 3
0.6725	Remote Similarity	NPD9269	Phase 2
0.6723	Remote Similarity	NPD1240	Approved
0.6722	Remote Similarity	NPD2935	Discontinued
0.672	Remote Similarity	NPD920	Approved
0.6717	Remote Similarity	NPD5953	Discontinued
0.6705	Remote Similarity	NPD3268	Approved
0.6703	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5710	Approved
0.6701	Remote Similarity	NPD5711	Approved
0.6685	Remote Similarity	NPD5124	Phase 1
0.6685	Remote Similarity	NPD2346	Discontinued
0.6685	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD8285	Discontinued
0.6682	Remote Similarity	NPD8059	Phase 3
0.6682	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4111	Phase 1
0.6667	Remote Similarity	NPD5005	Approved
0.6667	Remote Similarity	NPD5006	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