NPASS Compound

Structure

CID231518 OpenBabel06191716032D 50 56 0 0 1 0 0 0 0 0999 V2000 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5160 -2.1910 0.0000 C 0 0 0 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 -3.4641 -3.0000 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3926 -4.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2701 -4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0562 -2.5477 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 -8.6495 -3.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2646 -4.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2587 -3.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6713 -3.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 2 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 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 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 -4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7646 -5.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1722 -4.0371 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 -5.7038 -2.5664 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 -10.0508 -2.6522 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 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 35 1 0 0 0 0 4 45 1 0 0 0 0 5 6 1 0 0 0 0 5 18 1 0 0 0 0 6 21 1 0 0 0 0 7 9 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 20 1 0 0 0 0 9 34 1 0 0 0 0 10 35 1 0 0 0 0 11 17 2 0 0 0 0 11 24 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 22 1 0 0 0 0 13 36 1 0 0 0 0 14 37 1 0 0 0 0 15 17 1 0 0 0 0 15 46 1 0 0 0 0 16 1 1 6 0 0 0 16 30 1 0 0 0 0 16 47 1 0 0 0 0 17 25 1 0 0 0 0 18 34 1 1 0 0 0 19 48 1 6 0 0 0 20 21 1 0 0 0 0 20 34 1 6 0 0 0 21 36 1 1 0 0 0 22 25 1 0 0 0 0 22 38 1 6 0 0 0 23 14 1 6 0 0 0 23 26 1 0 0 0 0 23 49 1 0 0 0 0 24 39 2 0 0 0 0 24 46 1 0 0 0 0 25 35 1 6 0 0 0 26 27 1 0 0 0 0 26 40 1 1 0 0 0 27 28 1 0 0 0 0 27 41 1 6 0 0 0 28 32 1 0 0 0 0 28 42 1 1 0 0 0 29 31 1 0 0 0 0 29 33 1 0 0 0 0 29 43 1 1 0 0 0 30 31 1 0 0 0 0 30 50 1 6 0 0 0 31 45 1 6 0 0 0 32 49 1 0 0 0 0 32 50 1 6 0 0 0 33 47 1 0 0 0 0 33 48 1 6 0 0 0 34 2 1 6 0 0 0 35 36 1 6 0 0 0 36 44 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	712.37
Volume:	689.107
LogP:	1.999
LogD:	2.085
LogS:	-3.231
# Rotatable Bonds:	7
TPSA:	221.13
# H-Bond Aceptor:	14
# H-Bond Donor:	8
# Rings:	7
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.184
Synthetic Accessibility Score:	5.832
Fsp3:	0.889
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.458
MDCK Permeability:	8.17952022771351e-05
Pgp-inhibitor:	0.035
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.983
20% Bioavailability (F20%):	0.689
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.138
Plasma Protein Binding (PPB):	86.31804656982422%
Volume Distribution (VD):	0.291
Pgp-substrate:	11.85444164276123%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.658
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.22
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.084
CYP3A4-substrate:	0.088

ADMET: Excretion

Clearance (CL):	0.957
Half-life (T1/2):	0.705

ADMET: Toxicity

hERG Blockers:	0.311
Human Hepatotoxicity (H-HT):	0.249
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.329
Maximum Recommended Daily Dose:	0.681
Skin Sensitization:	0.904
Carcinogencity:	0.098
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC231518

Natural Product ID:	NPC231518
*Common Name:**	Digitalin
IUPAC Name:	3-[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14,16-dihydroxy-3-[(2R,3R,4R,5S,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms:	Digitalin
Standard InCHIKey:	CKNOLMVLQUPVMU-YMMLYESFSA-N
Standard InCHI:	InChI=1S/C36H56O14/c1-16-30(50-32-28(42)27(41)26(40)23(14-37)49-32)31(45-4)29(43)33(47-16)48-19-7-9-34(2)18(12-19)5-6-21-20(34)8-10-35(3)25(17-11-24(39)46-15-17)22(38)13-36(21,35)44/h11,16,18-23,25-33,37-38,40-44H,5-10,12-15H2,1-4H3/t16-,18-,19+,20+,21-,22+,23-,25+,26-,27+,28-,29-,30+,31-,32+,33+,34+,35-,36+/m1/s1
SMILES:	C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](C4=CC(=O)OC4)[C@H](C[C@]32O)O)C1)O)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505674
PubChem CID:	441856
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

*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
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.lwt.2014.11.023]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11277760]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19731587]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13401	Phoenix canariensis	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13401	Phoenix canariensis	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18930	Rubus coreanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1308	Veronica pectinata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8585	Verpa digitaliformis	Species	Morchellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6776	Trifolium apertum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6377	Cocculus diversifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2361	Aconitum brevicalcaratum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7097	Rhynchosporium orthosporum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4082	Ophiarthrum elegans	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6974	Solanum racemigerum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19441	Strychnos splendens	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8840	Ptilidium ciliare	Species	Ptilidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18180	Erysimum repandum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1607	Croton rhamnifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5591	Fucus spiralis	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20132	Scutellaria seleriana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18930	Rubus coreanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19175	Iguana iguana	Species	Iguanidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5980	Eria subsessilis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3146	Ammodendron conollyi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO715	Teucrium pestalozzae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13401	Phoenix canariensis	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8472	Knightia deplanchei	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15583	Tripodanthus acutifolius	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19093	Streptomyces aburaviensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12474	Cordyline fruticosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17635	Aria arguta	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO351	Cirsium dipsacolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4253	Viguiera annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27168	Atropa belladona	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5197	Streptomyces eurythermus	Species	Streptomycetaceae	Bacteria	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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ratio IC50	=	16000.0	n.a.	PMID[549842]

☑ 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 NPC231518 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	275
0.1-0.2	1858
0.2-0.3	5260
0.3-0.4	11769
0.4-0.5	9837
0.5-0.6	6631
0.6-0.7	4074
0.7-0.8	2056
0.8-0.85	543
0.85-0.9	240
0.9-0.95	79
0.95-1	75

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475219
0.9911	High Similarity	NPC193893
0.9821	High Similarity	NPC40749
0.982	High Similarity	NPC5883
0.982	High Similarity	NPC469756
0.982	High Similarity	NPC55532
0.982	High Similarity	NPC32177
0.982	High Similarity	NPC236973
0.982	High Similarity	NPC44899
0.982	High Similarity	NPC30483
0.982	High Similarity	NPC470897
0.982	High Similarity	NPC292467
0.982	High Similarity	NPC29639
0.982	High Similarity	NPC304260
0.9732	High Similarity	NPC72260
0.9732	High Similarity	NPC475629
0.9732	High Similarity	NPC475556
0.9732	High Similarity	NPC107607
0.9646	High Similarity	NPC314535
0.9646	High Similarity	NPC173555
0.9646	High Similarity	NPC475590
0.9646	High Similarity	NPC474908
0.9646	High Similarity	NPC475419
0.9646	High Similarity	NPC120390
0.9643	High Similarity	NPC329905
0.9643	High Similarity	NPC81222
0.9643	High Similarity	NPC291820
0.964	High Similarity	NPC93883
0.9561	High Similarity	NPC74259
0.9561	High Similarity	NPC264336
0.9561	High Similarity	NPC474423
0.9558	High Similarity	NPC474466
0.9558	High Similarity	NPC475136
0.9554	High Similarity	NPC218093
0.955	High Similarity	NPC193382
0.955	High Similarity	NPC5311
0.955	High Similarity	NPC99620
0.955	High Similarity	NPC199428
0.955	High Similarity	NPC310341
0.9478	High Similarity	NPC208193
0.9478	High Similarity	NPC117445
0.9478	High Similarity	NPC308262
0.9464	High Similarity	NPC34390
0.9464	High Similarity	NPC142066
0.9464	High Similarity	NPC471353
0.9464	High Similarity	NPC99728
0.9464	High Similarity	NPC309034
0.9464	High Similarity	NPC50305
0.9464	High Similarity	NPC196429
0.9464	High Similarity	NPC157376
0.9464	High Similarity	NPC471354
0.9464	High Similarity	NPC244402
0.9464	High Similarity	NPC473852
0.9464	High Similarity	NPC84987
0.9464	High Similarity	NPC243196
0.9464	High Similarity	NPC203862
0.9464	High Similarity	NPC27507
0.9464	High Similarity	NPC471351
0.9464	High Similarity	NPC474418
0.9464	High Similarity	NPC471355
0.9464	High Similarity	NPC158344
0.9464	High Similarity	NPC87250
0.9464	High Similarity	NPC77319
0.9464	High Similarity	NPC152615
0.9459	High Similarity	NPC471633
0.9459	High Similarity	NPC69576
0.9459	High Similarity	NPC84949
0.9459	High Similarity	NPC31354
0.9391	High Similarity	NPC115349
0.9381	High Similarity	NPC83287
0.9292	High Similarity	NPC290693
0.9237	High Similarity	NPC329784
0.9237	High Similarity	NPC240070
0.9083	High Similarity	NPC188234
0.9083	High Similarity	NPC232785
0.9083	High Similarity	NPC276838
0.9083	High Similarity	NPC140092
0.9083	High Similarity	NPC329986
0.9083	High Similarity	NPC125077
0.9052	High Similarity	NPC135369
0.9018	High Similarity	NPC114188
0.9016	High Similarity	NPC142756
0.9016	High Similarity	NPC225385
0.9016	High Similarity	NPC298783
0.9016	High Similarity	NPC157817
0.9016	High Similarity	NPC104585
0.8983	High Similarity	NPC27363
0.8966	High Similarity	NPC268326
0.8966	High Similarity	NPC153085
0.8919	High Similarity	NPC38217
0.8919	High Similarity	NPC472988
0.8889	High Similarity	NPC470312
0.8879	High Similarity	NPC475403
0.8879	High Similarity	NPC160888
0.887	High Similarity	NPC207637
0.8862	High Similarity	NPC32793
0.8862	High Similarity	NPC247190
0.8862	High Similarity	NPC116075
0.8862	High Similarity	NPC469749
0.8862	High Similarity	NPC476221
0.8862	High Similarity	NPC477709
0.8862	High Similarity	NPC146857
0.886	High Similarity	NPC144068
0.8852	High Similarity	NPC253456
0.8852	High Similarity	NPC159338
0.8852	High Similarity	NPC16569
0.885	High Similarity	NPC473021
0.885	High Similarity	NPC472987
0.8839	High Similarity	NPC43976
0.8839	High Similarity	NPC296761
0.8839	High Similarity	NPC51925
0.8839	High Similarity	NPC154085
0.8839	High Similarity	NPC125361
0.8839	High Similarity	NPC475030
0.8833	High Similarity	NPC250556
0.8833	High Similarity	NPC469750
0.8829	High Similarity	NPC234160
0.8803	High Similarity	NPC476085
0.8803	High Similarity	NPC229962
0.8803	High Similarity	NPC195560
0.8803	High Similarity	NPC473633
0.8793	High Similarity	NPC20979
0.8793	High Similarity	NPC476690
0.8793	High Similarity	NPC100048
0.879	High Similarity	NPC329636
0.878	High Similarity	NPC19124
0.878	High Similarity	NPC93416
0.878	High Similarity	NPC42670
0.877	High Similarity	NPC91
0.876	High Similarity	NPC471357
0.876	High Similarity	NPC471356
0.876	High Similarity	NPC146456
0.876	High Similarity	NPC469757
0.876	High Similarity	NPC117702
0.876	High Similarity	NPC179412
0.875	High Similarity	NPC295980
0.8739	High Similarity	NPC119855
0.8739	High Similarity	NPC220217
0.8739	High Similarity	NPC473199
0.8739	High Similarity	NPC471082
0.8739	High Similarity	NPC43842
0.8729	High Similarity	NPC50689
0.8729	High Similarity	NPC233391
0.8729	High Similarity	NPC207243
0.8729	High Similarity	NPC198325
0.872	High Similarity	NPC194716
0.8718	High Similarity	NPC10366
0.8718	High Similarity	NPC472080
0.8707	High Similarity	NPC146652
0.8699	High Similarity	NPC173347
0.8689	High Similarity	NPC311534
0.8684	High Similarity	NPC13190
0.8684	High Similarity	NPC65167
0.8678	High Similarity	NPC179261
0.8673	High Similarity	NPC472901
0.8673	High Similarity	NPC157530
0.8673	High Similarity	NPC14630
0.8673	High Similarity	NPC250089
0.8667	High Similarity	NPC202261
0.8667	High Similarity	NPC219804
0.8667	High Similarity	NPC106589
0.8667	High Similarity	NPC295133
0.8667	High Similarity	NPC257207
0.8661	High Similarity	NPC473469
0.8661	High Similarity	NPC231340
0.8651	High Similarity	NPC329675
0.8651	High Similarity	NPC59288
0.8644	High Similarity	NPC470914
0.8618	High Similarity	NPC251866
0.8618	High Similarity	NPC471359
0.8618	High Similarity	NPC180079
0.8618	High Similarity	NPC471358
0.8618	High Similarity	NPC469754
0.8618	High Similarity	NPC471361
0.8618	High Similarity	NPC197707
0.8618	High Similarity	NPC471352
0.8618	High Similarity	NPC469751
0.8618	High Similarity	NPC219085
0.8618	High Similarity	NPC70542
0.8618	High Similarity	NPC469752
0.8618	High Similarity	NPC17896
0.8618	High Similarity	NPC9499
0.8618	High Similarity	NPC6108
0.8618	High Similarity	NPC284406
0.8618	High Similarity	NPC86159
0.8618	High Similarity	NPC469755
0.8618	High Similarity	NPC89514
0.8618	High Similarity	NPC469753
0.8618	High Similarity	NPC471360
0.8618	High Similarity	NPC10823
0.8609	High Similarity	NPC112274
0.8609	High Similarity	NPC19888
0.8584	High Similarity	NPC7213
0.8584	High Similarity	NPC472897
0.8584	High Similarity	NPC472896
0.8571	High Similarity	NPC242748
0.8571	High Similarity	NPC472899
0.8571	High Similarity	NPC472900
0.8571	High Similarity	NPC475358
0.8571	High Similarity	NPC472898

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 NPC231518 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	237
0.1-0.2	1952
0.2-0.3	4086
0.3-0.4	1938
0.4-0.5	497
0.5-0.6	295
0.6-0.7	111
0.7-0.8	20
0.8-0.85	1
0.85-0.9	2
0.9-0.95	3
0.95-1	8

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8033	Approved
0.9732	High Similarity	NPD8294	Approved
0.9732	High Similarity	NPD8377	Approved
0.9646	High Similarity	NPD8296	Approved
0.9646	High Similarity	NPD8335	Approved
0.9646	High Similarity	NPD8380	Approved
0.9646	High Similarity	NPD8379	Approved
0.9646	High Similarity	NPD8378	Approved
0.9381	High Similarity	NPD7328	Approved
0.9381	High Similarity	NPD7327	Approved
0.9298	High Similarity	NPD7516	Approved
0.8833	High Similarity	NPD7507	Approved
0.8655	High Similarity	NPD7503	Approved
0.8618	High Similarity	NPD7319	Approved
0.822	Intermediate Similarity	NPD8133	Approved
0.7949	Intermediate Similarity	NPD6686	Approved
0.7754	Intermediate Similarity	NPD7625	Phase 1
0.7719	Intermediate Similarity	NPD7638	Approved
0.7712	Intermediate Similarity	NPD6412	Phase 2
0.7674	Intermediate Similarity	NPD7736	Approved
0.7652	Intermediate Similarity	NPD7640	Approved
0.7652	Intermediate Similarity	NPD7639	Approved
0.75	Intermediate Similarity	NPD8328	Phase 3
0.7462	Intermediate Similarity	NPD8293	Discontinued
0.7434	Intermediate Similarity	NPD8171	Discontinued
0.7302	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD6370	Approved
0.7209	Intermediate Similarity	NPD8513	Phase 3
0.7209	Intermediate Similarity	NPD8516	Approved
0.7209	Intermediate Similarity	NPD8515	Approved
0.7209	Intermediate Similarity	NPD8517	Approved
0.7176	Intermediate Similarity	NPD7492	Approved
0.7165	Intermediate Similarity	NPD7115	Discovery
0.7132	Intermediate Similarity	NPD6059	Approved
0.7132	Intermediate Similarity	NPD6054	Approved
0.7121	Intermediate Similarity	NPD6616	Approved
0.712	Intermediate Similarity	NPD6882	Approved
0.712	Intermediate Similarity	NPD8297	Approved
0.7107	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7632	Discontinued
0.7068	Intermediate Similarity	NPD7078	Approved
0.7031	Intermediate Similarity	NPD6009	Approved
0.7016	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6319	Approved
0.6984	Remote Similarity	NPD6053	Discontinued
0.6975	Remote Similarity	NPD4225	Approved
0.6947	Remote Similarity	NPD6016	Approved
0.6947	Remote Similarity	NPD6015	Approved
0.6935	Remote Similarity	NPD7320	Approved
0.6934	Remote Similarity	NPD8449	Approved
0.6929	Remote Similarity	NPD4632	Approved
0.6911	Remote Similarity	NPD6675	Approved
0.6911	Remote Similarity	NPD7128	Approved
0.6911	Remote Similarity	NPD5739	Approved
0.6911	Remote Similarity	NPD6402	Approved
0.6905	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5988	Approved
0.6884	Remote Similarity	NPD8450	Suspended
0.688	Remote Similarity	NPD6373	Approved
0.688	Remote Similarity	NPD6372	Approved
0.686	Remote Similarity	NPD5344	Discontinued
0.6842	Remote Similarity	NPD6067	Discontinued
0.6833	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6881	Approved
0.68	Remote Similarity	NPD6899	Approved
0.6774	Remote Similarity	NPD6008	Approved
0.6772	Remote Similarity	NPD8130	Phase 1
0.6772	Remote Similarity	NPD6649	Approved
0.6772	Remote Similarity	NPD6650	Approved
0.6724	Remote Similarity	NPD6051	Approved
0.672	Remote Similarity	NPD5697	Approved
0.672	Remote Similarity	NPD5701	Approved
0.6693	Remote Similarity	NPD6883	Approved
0.6693	Remote Similarity	NPD7290	Approved
0.6693	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD7525	Registered
0.6642	Remote Similarity	NPD6033	Approved
0.6641	Remote Similarity	NPD6617	Approved
0.6641	Remote Similarity	NPD6869	Approved
0.6641	Remote Similarity	NPD6847	Approved
0.6639	Remote Similarity	NPD7748	Approved
0.6614	Remote Similarity	NPD6014	Approved
0.6614	Remote Similarity	NPD6013	Approved
0.6614	Remote Similarity	NPD6012	Approved
0.6612	Remote Similarity	NPD6083	Phase 2
0.6612	Remote Similarity	NPD6084	Phase 2
0.6612	Remote Similarity	NPD7902	Approved
0.6593	Remote Similarity	NPD7604	Phase 2
0.6587	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD5983	Phase 2
0.6552	Remote Similarity	NPD7524	Approved
0.6535	Remote Similarity	NPD6011	Approved
0.6525	Remote Similarity	NPD7838	Discovery
0.6525	Remote Similarity	NPD46	Approved
0.6525	Remote Similarity	NPD6698	Approved
0.6518	Remote Similarity	NPD6928	Phase 2
0.6512	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6648	Approved
0.6496	Remote Similarity	NPD6336	Discontinued
0.6475	Remote Similarity	NPD4755	Approved
0.6471	Remote Similarity	NPD8034	Phase 2
0.6471	Remote Similarity	NPD8035	Phase 2
0.6471	Remote Similarity	NPD7515	Phase 2
0.6449	Remote Similarity	NPD8074	Phase 3
0.6442	Remote Similarity	NPD7799	Discontinued
0.6435	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD6371	Approved
0.6434	Remote Similarity	NPD4634	Approved
0.6417	Remote Similarity	NPD6399	Phase 3
0.6417	Remote Similarity	NPD4202	Approved
0.641	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5211	Phase 2
0.6371	Remote Similarity	NPD5285	Approved
0.6371	Remote Similarity	NPD4700	Approved
0.6371	Remote Similarity	NPD5286	Approved
0.6371	Remote Similarity	NPD4696	Approved
0.6364	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7900	Approved
0.6356	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6695	Phase 3
0.6333	Remote Similarity	NPD7637	Suspended
0.632	Remote Similarity	NPD4159	Approved
0.6316	Remote Similarity	NPD6274	Approved
0.6311	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5695	Phase 3
0.6299	Remote Similarity	NPD5141	Approved
0.6296	Remote Similarity	NPD7100	Approved
0.6296	Remote Similarity	NPD7101	Approved
0.629	Remote Similarity	NPD5696	Approved
0.6283	Remote Similarity	NPD7645	Phase 2
0.6271	Remote Similarity	NPD7750	Discontinued
0.627	Remote Similarity	NPD5225	Approved
0.627	Remote Similarity	NPD5224	Approved
0.627	Remote Similarity	NPD4633	Approved
0.627	Remote Similarity	NPD5226	Approved
0.625	Remote Similarity	NPD4768	Approved
0.625	Remote Similarity	NPD4767	Approved
0.6239	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6335	Approved
0.622	Remote Similarity	NPD5174	Approved
0.622	Remote Similarity	NPD5175	Approved
0.6218	Remote Similarity	NPD6903	Approved
0.6204	Remote Similarity	NPD6908	Approved
0.6204	Remote Similarity	NPD6909	Approved
0.6198	Remote Similarity	NPD5693	Phase 1
0.6197	Remote Similarity	NPD5956	Approved
0.619	Remote Similarity	NPD5223	Approved
0.6186	Remote Similarity	NPD7334	Approved
0.6186	Remote Similarity	NPD7146	Approved
0.6186	Remote Similarity	NPD6684	Approved
0.6186	Remote Similarity	NPD6409	Approved
0.6186	Remote Similarity	NPD5330	Approved
0.6186	Remote Similarity	NPD7521	Approved
0.617	Remote Similarity	NPD8336	Approved
0.617	Remote Similarity	NPD8337	Approved
0.6167	Remote Similarity	NPD4753	Phase 2
0.6167	Remote Similarity	NPD5328	Approved
0.6161	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4729	Approved
0.6154	Remote Similarity	NPD4730	Approved
0.6148	Remote Similarity	NPD6317	Approved
0.6134	Remote Similarity	NPD4250	Approved
0.6134	Remote Similarity	NPD4251	Approved
0.6103	Remote Similarity	NPD6313	Approved
0.6103	Remote Similarity	NPD6314	Approved
0.6102	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD4754	Approved
0.6087	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6931	Approved
0.6087	Remote Similarity	NPD6930	Phase 2
0.6071	Remote Similarity	NPD7339	Approved
0.6071	Remote Similarity	NPD6942	Approved
0.6066	Remote Similarity	NPD6079	Approved
0.6061	Remote Similarity	NPD5248	Approved
0.6061	Remote Similarity	NPD5249	Phase 3
0.6061	Remote Similarity	NPD5251	Approved
0.6061	Remote Similarity	NPD5250	Approved
0.6061	Remote Similarity	NPD5247	Approved
0.605	Remote Similarity	NPD4249	Approved
0.605	Remote Similarity	NPD3618	Phase 1
0.6042	Remote Similarity	NPD7260	Phase 2
0.6033	Remote Similarity	NPD6673	Approved
0.6033	Remote Similarity	NPD6080	Approved
0.6033	Remote Similarity	NPD6904	Approved
0.6031	Remote Similarity	NPD5128	Approved
0.6018	Remote Similarity	NPD6933	Approved
0.6017	Remote Similarity	NPD4786	Approved
0.6017	Remote Similarity	NPD3133	Approved
0.6017	Remote Similarity	NPD3665	Phase 1
0.6017	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD4195	Approved
0.6	Remote Similarity	NPD7829	Approved
0.6	Remote Similarity	NPD7830	Approved
0.6	Remote Similarity	NPD8338	Approved
0.6	Remote Similarity	NPD6929	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