NPASS Compound

Structure

CID52021 OpenBabel06191715392D 34 38 0 0 1 0 0 0 0 0999 V2000 -4.4713 -0.4540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9921 1.0803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5058 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0186 -0.6177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6876 -2.9231 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5315 -2.4359 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5315 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5315 1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 -3.8974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 18 2 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 29 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 30 1 0 0 0 0 16 19 1 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 0 0 0 0 19 30 1 6 0 0 0 20 23 1 0 0 0 0 20 31 1 6 0 0 0 21 26 1 0 0 0 0 21 27 1 1 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 26 1 0 0 0 0 23 32 1 6 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	313.13
Volume:	327.837
LogP:	2.439
LogD:	2.898
LogS:	-3.674
# Rotatable Bonds:	7
TPSA:	78.79
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.716
Synthetic Accessibility Score:	2.011
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.847
MDCK Permeability:	1.1772313882829621e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	95.90667724609375%
Volume Distribution (VD):	0.549
Pgp-substrate:	2.533156156539917%

ADMET: Metabolism

CYP1A2-inhibitor:	0.931
CYP1A2-substrate:	0.335
CYP2C19-inhibitor:	0.82
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.763
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.794
CYP2D6-substrate:	0.898
CYP3A4-inhibitor:	0.867
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	12.668
Half-life (T1/2):	0.906

ADMET: Toxicity

hERG Blockers:	0.3
Human Hepatotoxicity (H-HT):	0.288
Drug-inuced Liver Injury (DILI):	0.231
AMES Toxicity:	0.348
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.228
Skin Sensitization:	0.885
Carcinogencity:	0.553
Eye Corrosion:	0.004
Eye Irritation:	0.19
Respiratory Toxicity:	0.114

Download Data

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

Natural Product: NPC52021

Natural Product ID:	NPC52021
*Common Name:**	3-Epimaslinic Acid
IUPAC Name:	(4aS,6aR,6aS,6bR,8aR,10S,11R,12aR,14bS)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:	3-Epi-Masilinic Acid; 3-Epi-Maslinic Acid; 3-Epimaslinic Acid
Standard InCHIKey:	MDZKJHQSJHYOHJ-HFYZCPLSSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-25(2)12-14-30(24(33)34)15-13-28(6)18(19(30)16-25)8-9-22-27(5)17-20(31)23(32)26(3,4)21(27)10-11-29(22,28)7/h8,19-23,31-32H,9-17H2,1-7H3,(H,33,34)/t19-,20+,21-,22+,23+,27-,28+,29+,30-/m0/s1
SMILES:	O[C@@H]1C[C@@]2(C)[C@H](C([C@@H]1O)(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL383749
PubChem CID:	25564831
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF02675902]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11816-015-0350-y]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/0031-9422(86)88033-5]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/0031-9422(86)88033-5]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	whole plant	n.a.	n.a.	DOI[10.1016/j.tetlet.2016.12.029]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1055/s-2008-1074888]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1248/cpb.30.4088]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10353265]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10553679]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11720520]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12055308]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14600382]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15070765]
NPO28035	Streptomyces fumanus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15730262]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16038540]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	PMID[1612412]
NPO28391	Euonymus nanoides	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	PMID[16462067]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17520525]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18327911]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	roots	Gabon	1987	PMID[18327911]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO8068	Blumea mollis	Species	Asteraceae	Eukaryota	n.a.	leaf	n.a.	PMID[18566831]
NPO14162	Chlorophytum borivilianum	Species	Asparagaceae	Eukaryota	roots	n.a.	n.a.	PMID[19128156]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19276083]
NPO7016	Gardenia tubifera	Species	Rubiaceae	Eukaryota	exudate	n.a.	n.a.	PMID[20028108]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20448045]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20509707]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20550123]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20674349]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20843794]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[21428274]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21428274]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22194604]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22272932]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22530813]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22966846]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964677]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24516143]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25028392]
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25245917]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25320841]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26169681]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26466957]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26774486]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26938998]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26996316]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27242221]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27807341]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5583807]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8917504]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[97292]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4004	Aquilegia ecalcarata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16703	Isodon lophanthoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28391	Euonymus nanoides	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12509	Dipterocarpus dyeri	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27959	Codonocarpus australis	Species	Gyrostemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28035	Streptomyces fumanus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28374	Pleogyne cunninghami	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8892	Sordaria araneosa	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17494	Prunella vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22758	Picradeniopsis pringlei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4004	Aquilegia ecalcarata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11998	Ledebouria socialis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27990	Schizonepeta multifida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28073	Crateva nurvala	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6331	Jacobaea subalpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28670	Mortierella elongata	Species	Mortierellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO746	Panax innovans	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28200	Unonopsis glaucopetala	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28481	Cerbera dilatata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25704	Tetraneuris acaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28269	Rubus rosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28633	Bystropogon origanifolius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5191	Penicillium cinerascens	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13766	Ceanothus velutinus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16669	Diospyros verrucosa	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28704	Agaricus hortensis	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7016	Gardenia tubifera	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12800	Glycine falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28131	Polygala amara	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO205	Lasianthus fordii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20395	Athanasia crithmifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4671	Persea mexicana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14057	Apollonias barbujana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28053	Quercus serrata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10550	Artemisia hanseniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28509	Achillea clypeolata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16703	Isodon lophanthoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8068	Blumea mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29353	Benzoin praecox	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28656	Lactobacillus casei	Species	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28303	Pleogyne cunninghamii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13467	Anarsia lineatella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28161	Stephania sutchuenensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28614	Zieria smithii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27943	Cardamine pinnata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28691	Streptomyces odorifer	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28596	Streptomyces lavendofoliae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29115	Rhinella arenarum	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6321	Agathosma thymifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14162	Chlorophytum borivilianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27867	Turbo argyrostoma	Species	Turbinidae	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
GI50	3
IC50	12
Others	3

Activity Type	# Activity
Cell Line	10
Individual Protein	7
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2681	Individual Protein	Glycogen phosphorylase, muscle form	Oryctolagus cuniculus	IC50	=	144000.0	nM	PMID[529800]
NPT2681	Individual Protein	Glycogen phosphorylase, muscle form	Oryctolagus cuniculus	IC50	=	144000.0	nM	PMID[529801]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	14330.0	nM	PMID[529802]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	22100.0	nM	PMID[529803]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	41730.0	nM	PMID[529803]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	19520.0	nM	PMID[529803]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	12530.0	nM	PMID[529803]
NPT2681	Individual Protein	Glycogen phosphorylase, muscle form	Oryctolagus cuniculus	IC50	=	144000.0	nM	PMID[529804]
NPT2681	Individual Protein	Glycogen phosphorylase, muscle form	Oryctolagus cuniculus	IC50	=	144543.98	nM	PMID[529804]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	27700.0	nM	PMID[529805]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	21600.0	nM	PMID[529807]
NPT34	Cell Line	BV-2	Mus musculus	Activity	=	87.0	%	PMID[529807]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	IC50	>	100000.0	nM	PMID[529808]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	=	51000.0	nM	PMID[529808]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Inhibition	=	20.0	%	PMID[529808]
NPT81	Cell Line	A549	Homo sapiens	GI50	>	100000.0	nM	PMID[529808]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	>	100000.0	nM	PMID[529808]
NPT21657	SINGLE PROTEIN	DNA topoisomerase I	Bos taurus	Inhibition	=	30.0	%	PMID[529808]

☑ 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 NPC52021 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	208
0.1-0.2	1320
0.2-0.3	4770
0.3-0.4	14065
0.4-0.5	9392
0.5-0.6	5404
0.6-0.7	4760
0.7-0.8	2018
0.8-0.85	413
0.85-0.9	131
0.9-0.95	137
0.95-1	79

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC300351
1.0	High Similarity	NPC84319
1.0	High Similarity	NPC306541
1.0	High Similarity	NPC25299
1.0	High Similarity	NPC235884
1.0	High Similarity	NPC71074
1.0	High Similarity	NPC472149
0.9884	High Similarity	NPC307335
0.9884	High Similarity	NPC275809
0.9884	High Similarity	NPC136313
0.9884	High Similarity	NPC74855
0.9882	High Similarity	NPC49320
0.977	High Similarity	NPC32407
0.977	High Similarity	NPC145667
0.977	High Similarity	NPC88116
0.977	High Similarity	NPC299996
0.977	High Similarity	NPC231063
0.977	High Similarity	NPC282395
0.977	High Similarity	NPC263548
0.977	High Similarity	NPC20235
0.9659	High Similarity	NPC198245
0.9659	High Similarity	NPC96916
0.9655	High Similarity	NPC133579
0.9655	High Similarity	NPC474806
0.9647	High Similarity	NPC52169
0.9647	High Similarity	NPC182797
0.9551	High Similarity	NPC158371
0.9551	High Similarity	NPC259733
0.9551	High Similarity	NPC19376
0.9551	High Similarity	NPC307282
0.9551	High Similarity	NPC204961
0.9551	High Similarity	NPC305464
0.9551	High Similarity	NPC73004
0.9551	High Similarity	NPC207922
0.9551	High Similarity	NPC230151
0.9551	High Similarity	NPC201657
0.9551	High Similarity	NPC25848
0.9551	High Similarity	NPC173744
0.9545	High Similarity	NPC188102
0.9545	High Similarity	NPC87095
0.9535	High Similarity	NPC130520
0.9535	High Similarity	NPC225585
0.9535	High Similarity	NPC234346
0.9535	High Similarity	NPC61543
0.9535	High Similarity	NPC127689
0.9535	High Similarity	NPC59263
0.9535	High Similarity	NPC263393
0.9535	High Similarity	NPC274330
0.9535	High Similarity	NPC270768
0.9535	High Similarity	NPC143232
0.9535	High Similarity	NPC121798
0.9535	High Similarity	NPC293048
0.9535	High Similarity	NPC290972
0.9535	High Similarity	NPC25906
0.9535	High Similarity	NPC198664
0.9535	High Similarity	NPC64872
0.9529	High Similarity	NPC130577
0.9529	High Similarity	NPC293564
0.9529	High Similarity	NPC88716
0.9529	High Similarity	NPC142415
0.9529	High Similarity	NPC98442
0.9529	High Similarity	NPC18064
0.9529	High Similarity	NPC68160
0.9529	High Similarity	NPC307426
0.9529	High Similarity	NPC171203
0.9529	High Similarity	NPC102683
0.9529	High Similarity	NPC51700
0.9529	High Similarity	NPC242468
0.9444	High Similarity	NPC261935
0.9444	High Similarity	NPC43686
0.9444	High Similarity	NPC9613
0.9444	High Similarity	NPC259788
0.9444	High Similarity	NPC106112
0.9444	High Similarity	NPC255589
0.9444	High Similarity	NPC247139
0.9438	High Similarity	NPC32118
0.9425	High Similarity	NPC120968
0.9425	High Similarity	NPC470589
0.9425	High Similarity	NPC227467
0.9425	High Similarity	NPC210037
0.9425	High Similarity	NPC477872
0.9425	High Similarity	NPC111110
0.9425	High Similarity	NPC273621
0.9425	High Similarity	NPC18872
0.9425	High Similarity	NPC290614
0.9425	High Similarity	NPC291028
0.9425	High Similarity	NPC126369
0.9425	High Similarity	NPC130278
0.9425	High Similarity	NPC7260
0.9419	High Similarity	NPC246708
0.9419	High Similarity	NPC470629
0.9419	High Similarity	NPC473242
0.9419	High Similarity	NPC17733
0.9419	High Similarity	NPC40552
0.9419	High Similarity	NPC474512
0.9419	High Similarity	NPC181225
0.9419	High Similarity	NPC290690
0.9412	High Similarity	NPC72638
0.9341	High Similarity	NPC111214
0.9341	High Similarity	NPC29765
0.9341	High Similarity	NPC188833
0.9341	High Similarity	NPC271614
0.9326	High Similarity	NPC296164
0.9318	High Similarity	NPC65120
0.9318	High Similarity	NPC187722
0.9318	High Similarity	NPC145067
0.9318	High Similarity	NPC105189
0.9318	High Similarity	NPC155120
0.9318	High Similarity	NPC282616
0.9318	High Similarity	NPC158030
0.9318	High Similarity	NPC233455
0.9318	High Similarity	NPC228784
0.9318	High Similarity	NPC4036
0.9318	High Similarity	NPC474525
0.9318	High Similarity	NPC288833
0.9318	High Similarity	NPC324341
0.9318	High Similarity	NPC966
0.931	High Similarity	NPC474972
0.931	High Similarity	NPC161751
0.931	High Similarity	NPC470588
0.931	High Similarity	NPC95246
0.9239	High Similarity	NPC35239
0.9231	High Similarity	NPC312075
0.9231	High Similarity	NPC203343
0.9213	High Similarity	NPC214756
0.9213	High Similarity	NPC86368
0.9213	High Similarity	NPC158059
0.9213	High Similarity	NPC298554
0.9213	High Similarity	NPC118519
0.9213	High Similarity	NPC202728
0.9213	High Similarity	NPC229281
0.9213	High Similarity	NPC295643
0.9213	High Similarity	NPC272075
0.9205	High Similarity	NPC46441
0.9205	High Similarity	NPC86372
0.9205	High Similarity	NPC193750
0.9205	High Similarity	NPC172361
0.9205	High Similarity	NPC113989
0.9205	High Similarity	NPC120840
0.9205	High Similarity	NPC474728
0.914	High Similarity	NPC233012
0.914	High Similarity	NPC256247
0.914	High Similarity	NPC54909
0.9121	High Similarity	NPC88847
0.9111	High Similarity	NPC222047
0.9111	High Similarity	NPC209868
0.9111	High Similarity	NPC159365
0.9111	High Similarity	NPC474529
0.9111	High Similarity	NPC114159
0.9111	High Similarity	NPC191412
0.9111	High Similarity	NPC6818
0.9111	High Similarity	NPC91010
0.9101	High Similarity	NPC189520
0.9101	High Similarity	NPC6255
0.9101	High Similarity	NPC77099
0.9101	High Similarity	NPC38754
0.9101	High Similarity	NPC475708
0.9101	High Similarity	NPC285184
0.9101	High Similarity	NPC471588
0.9101	High Similarity	NPC60755
0.9101	High Similarity	NPC470590
0.9091	High Similarity	NPC30522
0.9091	High Similarity	NPC474686
0.908	High Similarity	NPC71507
0.907	High Similarity	NPC133954
0.9011	High Similarity	NPC148523
0.9011	High Similarity	NPC474727
0.9011	High Similarity	NPC473240
0.9011	High Similarity	NPC139570
0.9	High Similarity	NPC49776
0.9	High Similarity	NPC118490
0.9	High Similarity	NPC474436
0.9	High Similarity	NPC63118
0.8966	High Similarity	NPC73038
0.8966	High Similarity	NPC324063
0.8966	High Similarity	NPC235341
0.8966	High Similarity	NPC477579
0.8966	High Similarity	NPC74363
0.8966	High Similarity	NPC95594
0.8966	High Similarity	NPC213412
0.8966	High Similarity	NPC475862
0.8953	High Similarity	NPC171789
0.8913	High Similarity	NPC132824
0.8913	High Similarity	NPC327179
0.8913	High Similarity	NPC62516
0.8913	High Similarity	NPC98874
0.8913	High Similarity	NPC476327
0.8913	High Similarity	NPC157113
0.8913	High Similarity	NPC116457
0.8913	High Similarity	NPC476318
0.8901	High Similarity	NPC80365
0.8901	High Similarity	NPC60692
0.8901	High Similarity	NPC78580
0.8901	High Similarity	NPC74751
0.8901	High Similarity	NPC184006
0.8901	High Similarity	NPC23621
0.8889	High Similarity	NPC301244
0.8876	High Similarity	NPC281524
0.8876	High Similarity	NPC220498
0.8864	High Similarity	NPC73064

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 NPC52021 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1702
0.2-0.3	3817
0.3-0.4	2300
0.4-0.5	690
0.5-0.6	209
0.6-0.7	197
0.7-0.8	41
0.8-0.85	4
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9318	High Similarity	NPD7515	Phase 2
0.8901	High Similarity	NPD7748	Approved
0.8617	High Similarity	NPD7902	Approved
0.8427	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD7900	Approved
0.8161	Intermediate Similarity	NPD7645	Phase 2
0.7935	Intermediate Similarity	NPD3618	Phase 1
0.7912	Intermediate Similarity	NPD4786	Approved
0.7895	Intermediate Similarity	NPD8034	Phase 2
0.7895	Intermediate Similarity	NPD8035	Phase 2
0.7889	Intermediate Similarity	NPD3667	Approved
0.7872	Intermediate Similarity	NPD5328	Approved
0.7812	Intermediate Similarity	NPD6399	Phase 3
0.7708	Intermediate Similarity	NPD6079	Approved
0.7684	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7638	Approved
0.7579	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD3666	Approved
0.7527	Intermediate Similarity	NPD3665	Phase 1
0.7527	Intermediate Similarity	NPD3133	Approved
0.7525	Intermediate Similarity	NPD7640	Approved
0.7525	Intermediate Similarity	NPD7639	Approved
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD6402	Approved
0.7473	Intermediate Similarity	NPD7525	Registered
0.7449	Intermediate Similarity	NPD4202	Approved
0.7416	Intermediate Similarity	NPD6117	Approved
0.74	Intermediate Similarity	NPD5221	Approved
0.74	Intermediate Similarity	NPD4697	Phase 3
0.74	Intermediate Similarity	NPD5222	Approved
0.74	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6684	Approved
0.7368	Intermediate Similarity	NPD8328	Phase 3
0.7368	Intermediate Similarity	NPD7146	Approved
0.7368	Intermediate Similarity	NPD5330	Approved
0.7368	Intermediate Similarity	NPD7521	Approved
0.7368	Intermediate Similarity	NPD7334	Approved
0.7368	Intermediate Similarity	NPD6409	Approved
0.7358	Intermediate Similarity	NPD7320	Approved
0.7358	Intermediate Similarity	NPD6899	Approved
0.7358	Intermediate Similarity	NPD6881	Approved
0.7347	Intermediate Similarity	NPD6411	Approved
0.734	Intermediate Similarity	NPD3668	Phase 3
0.7333	Intermediate Similarity	NPD6116	Phase 1
0.7327	Intermediate Similarity	NPD6084	Phase 2
0.7327	Intermediate Similarity	NPD6083	Phase 2
0.7327	Intermediate Similarity	NPD5173	Approved
0.7327	Intermediate Similarity	NPD4755	Approved
0.7297	Intermediate Similarity	NPD7115	Discovery
0.7297	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3573	Approved
0.729	Intermediate Similarity	NPD6373	Approved
0.729	Intermediate Similarity	NPD6372	Approved
0.7264	Intermediate Similarity	NPD5701	Approved
0.7264	Intermediate Similarity	NPD5697	Approved
0.7253	Intermediate Similarity	NPD6115	Approved
0.7253	Intermediate Similarity	NPD6118	Approved
0.7253	Intermediate Similarity	NPD6114	Approved
0.7253	Intermediate Similarity	NPD6697	Approved
0.7248	Intermediate Similarity	NPD8297	Approved
0.7228	Intermediate Similarity	NPD7614	Phase 1
0.7222	Intermediate Similarity	NPD6883	Approved
0.7222	Intermediate Similarity	NPD7102	Approved
0.7222	Intermediate Similarity	NPD7290	Approved
0.7216	Intermediate Similarity	NPD6903	Approved
0.7216	Intermediate Similarity	NPD6672	Approved
0.7216	Intermediate Similarity	NPD5737	Approved
0.7196	Intermediate Similarity	NPD6011	Approved
0.7191	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5286	Approved
0.7184	Intermediate Similarity	NPD5285	Approved
0.7184	Intermediate Similarity	NPD4700	Approved
0.7184	Intermediate Similarity	NPD4696	Approved
0.7182	Intermediate Similarity	NPD4632	Approved
0.7156	Intermediate Similarity	NPD8130	Phase 1
0.7156	Intermediate Similarity	NPD6650	Approved
0.7156	Intermediate Similarity	NPD6617	Approved
0.7156	Intermediate Similarity	NPD6869	Approved
0.7156	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6649	Approved
0.7156	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD4753	Phase 2
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6012	Approved
0.713	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6013	Approved
0.713	Intermediate Similarity	NPD6014	Approved
0.7115	Intermediate Similarity	NPD5223	Approved
0.7111	Intermediate Similarity	NPD7339	Approved
0.7111	Intermediate Similarity	NPD6942	Approved
0.7103	Intermediate Similarity	NPD6412	Phase 2
0.7097	Intermediate Similarity	NPD4695	Discontinued
0.7091	Intermediate Similarity	NPD6882	Approved
0.7087	Intermediate Similarity	NPD4225	Approved
0.7048	Intermediate Similarity	NPD5211	Phase 2
0.7048	Intermediate Similarity	NPD4633	Approved
0.7048	Intermediate Similarity	NPD5226	Approved
0.7048	Intermediate Similarity	NPD5224	Approved
0.7048	Intermediate Similarity	NPD5225	Approved
0.7033	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5279	Phase 3
0.701	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5175	Approved
0.6981	Remote Similarity	NPD4754	Approved
0.6981	Remote Similarity	NPD5174	Approved
0.6961	Remote Similarity	NPD5695	Phase 3
0.6961	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4223	Phase 3
0.6947	Remote Similarity	NPD4221	Approved
0.6923	Remote Similarity	NPD5696	Approved
0.6916	Remote Similarity	NPD5141	Approved
0.6909	Remote Similarity	NPD4634	Approved
0.6907	Remote Similarity	NPD5329	Approved
0.6903	Remote Similarity	NPD6868	Approved
0.6893	Remote Similarity	NPD7732	Phase 3
0.6887	Remote Similarity	NPD7632	Discontinued
0.6881	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6686	Approved
0.6875	Remote Similarity	NPD8133	Approved
0.6875	Remote Similarity	NPD4788	Approved
0.6852	Remote Similarity	NPD4768	Approved
0.6852	Remote Similarity	NPD4767	Approved
0.6842	Remote Similarity	NPD6009	Approved
0.6837	Remote Similarity	NPD6098	Approved
0.6832	Remote Similarity	NPD5281	Approved
0.6832	Remote Similarity	NPD5284	Approved
0.681	Remote Similarity	NPD6319	Approved
0.6807	Remote Similarity	NPD7507	Approved
0.6804	Remote Similarity	NPD4197	Approved
0.68	Remote Similarity	NPD6080	Approved
0.68	Remote Similarity	NPD6673	Approved
0.68	Remote Similarity	NPD6904	Approved
0.6796	Remote Similarity	NPD5210	Approved
0.6796	Remote Similarity	NPD4629	Approved
0.6783	Remote Similarity	NPD6335	Approved
0.6778	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5779	Approved
0.6765	Remote Similarity	NPD5778	Approved
0.6757	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6274	Approved
0.6742	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4730	Approved
0.6727	Remote Similarity	NPD5168	Approved
0.6727	Remote Similarity	NPD4729	Approved
0.6727	Remote Similarity	NPD5128	Approved
0.6724	Remote Similarity	NPD7100	Approved
0.6724	Remote Similarity	NPD7101	Approved
0.6702	Remote Similarity	NPD3617	Approved
0.6702	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6008	Approved
0.6696	Remote Similarity	NPD6317	Approved
0.6694	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD6933	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD4693	Phase 3
0.6639	Remote Similarity	NPD7319	Approved
0.6639	Remote Similarity	NPD7604	Phase 2
0.6638	Remote Similarity	NPD6314	Approved
0.6638	Remote Similarity	NPD6313	Approved
0.661	Remote Similarity	NPD5983	Phase 2
0.661	Remote Similarity	NPD6909	Approved
0.661	Remote Similarity	NPD6908	Approved
0.6607	Remote Similarity	NPD5251	Approved
0.6607	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5250	Approved
0.6607	Remote Similarity	NPD5249	Phase 3
0.6607	Remote Similarity	NPD5169	Approved
0.6607	Remote Similarity	NPD5247	Approved
0.6607	Remote Similarity	NPD5248	Approved
0.6607	Remote Similarity	NPD5135	Approved
0.6583	Remote Similarity	NPD7492	Approved
0.6581	Remote Similarity	NPD7516	Approved
0.6566	Remote Similarity	NPD1694	Approved
0.6562	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD3703	Phase 2
0.6549	Remote Similarity	NPD5127	Approved
0.6549	Remote Similarity	NPD5215	Approved
0.6549	Remote Similarity	NPD5216	Approved
0.6549	Remote Similarity	NPD5217	Approved
0.6538	Remote Similarity	NPD6001	Approved
0.6535	Remote Similarity	NPD5208	Approved
0.6529	Remote Similarity	NPD6336	Discontinued
0.6529	Remote Similarity	NPD6616	Approved
0.6525	Remote Similarity	NPD8377	Approved
0.6525	Remote Similarity	NPD6059	Approved
0.6525	Remote Similarity	NPD6054	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