NPASS Compound

Structure

NPC261245 OpenBabel06302215532D 66 73 0 0 1 0 0 0 0 0999 V2000 7.6889 1.4797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8346 0.9865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8346 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9803 -0.4932 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1259 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1259 0.9865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9803 1.4797 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2716 1.4797 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2716 2.4662 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1259 2.9595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1259 3.9459 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2716 4.4392 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2716 5.4257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4173 5.9189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4173 3.9459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4173 2.9595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5630 2.4662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7086 2.9595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7086 3.9459 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8543 4.4392 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 3.9459 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8543 4.4392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7086 3.9459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8543 5.4257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8543 2.4662 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8543 1.4797 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8543 1.4797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7086 0.9865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7086 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5630 0.4932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8543 -0.4932 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8543 -1.4797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7086 -1.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5630 -1.4797 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5630 -3.4527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5630 -0.4932 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4173 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2716 -0.4932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2716 -1.4797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1259 -1.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9803 -1.4797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8346 -1.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8211 -1.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3278 -1.1187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8346 -2.9595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9803 -3.4527 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1259 -2.9595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1259 -3.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2716 -3.4527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4173 -2.9595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4173 -1.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5630 -2.4662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9803 -4.4392 0.0000 O 0 0 0 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 0.9865 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4932 -0.8543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7086 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8543 5.4257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5630 4.4392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9803 4.4392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9803 2.4662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2716 -0.4932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9803 -1.4797 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6889 -0.4932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 0 0 0 2 3 1 0 0 0 0 2 7 1 0 0 0 0 3 4 1 0 0 0 0 3 66 1 6 0 0 0 4 5 1 0 0 0 0 4 65 1 1 0 0 0 5 6 1 0 0 0 0 5 64 1 6 0 0 0 6 7 1 0 0 0 0 6 8 1 1 0 0 0 9 8 1 6 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 63 1 1 0 0 0 11 12 1 0 0 0 0 11 62 1 6 0 0 0 12 13 1 1 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 1 0 0 0 18 17 1 6 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 61 1 1 0 0 0 20 21 1 0 0 0 0 20 60 1 6 0 0 0 21 22 1 1 0 0 0 21 25 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 25 26 1 0 0 0 0 26 27 1 1 0 0 0 28 27 1 6 0 0 0 28 29 1 0 0 0 0 28 56 1 0 0 0 0 29 30 1 0 0 0 0 30 31 1 0 0 0 0 31 38 1 0 0 0 0 31 32 1 6 0 0 0 31 33 1 0 0 0 0 33 34 1 6 0 0 0 33 56 1 0 0 0 0 34 35 1 0 0 0 0 35 36 1 0 0 0 0 36 53 1 0 0 0 0 36 37 1 6 0 0 0 36 38 1 0 0 0 0 38 39 1 6 0 0 0 39 40 1 0 0 0 0 40 41 2 0 0 0 0 41 53 1 0 0 0 0 41 42 1 0 0 0 0 42 43 1 6 0 0 0 42 49 1 0 0 0 0 43 44 1 0 0 0 0 44 45 1 0 0 0 0 44 46 1 0 0 0 0 44 47 1 0 0 0 0 47 48 1 0 0 0 0 48 49 1 0 0 0 0 48 55 1 6 0 0 0 49 50 1 1 0 0 0 49 51 1 0 0 0 0 51 52 1 0 0 0 0 52 53 1 0 0 0 0 53 54 1 1 0 0 0 56 57 1 6 0 0 0 56 58 1 0 0 0 0 58 59 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	942.52
Volume:	923.263
LogP:	1.932
LogD:	1.502
LogS:	-3.704
# Rotatable Bonds:	9
TPSA:	294.98
# H-Bond Aceptor:	18
# H-Bond Donor:	11
# Rings:	8
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.112
Synthetic Accessibility Score:	6.408
Fsp3:	0.938
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:	-5.999
MDCK Permeability:	4.680429265135899e-05
Pgp-inhibitor:	0.628
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.953
20% Bioavailability (F20%):	0.097
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	81.26017761230469%
Volume Distribution (VD):	0.187
Pgp-substrate:	11.83016586303711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.28
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	0.484
Half-life (T1/2):	0.745

ADMET: Toxicity

hERG Blockers:	0.094
Human Hepatotoxicity (H-HT):	0.189
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.094
Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.097
Skin Sensitization:	0.096
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.873

Download Data

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

Natural Product: NPC261245

Natural Product ID:	NPC261245
*Common Name:**	PTDAHAWQAGSZDD-ZFNUSGPSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PTDAHAWQAGSZDD-ZFNUSGPSSA-N
Standard InCHI:	InChI=1S/C48H78O18/c1-21-29(52)31(54)35(58)40(61-21)65-37-32(55)30(53)24(19-49)62-41(37)66-38-34(57)33(56)36(39(59)60)64-42(38)63-28-12-13-45(5)25(46(28,6)20-50)11-14-48(8)26(45)10-9-22-23-17-43(2,3)18-27(51)44(23,4)15-16-47(22,48)7/h9,21,23-38,40-42,49-58H,10-20H2,1-8H3,(H,59,60)/t21-,23+,24-,25+,26+,27+,28-,29-,30-,31+,32+,33+,34+,35-,36+,37-,38-,40+,41+,42-,44-,45-,46-,47+,48+/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)O[C@H]1[C@@H]([C@H]([C@H](CO)O[C@@H]1O[C@H]1[C@@H]([C@H]([C@H](C(=O)O)O[C@@H]1O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@H]4CC(C)(C)C[C@H]([C@@]4(C)CC[C@@]32C)O)[C@]1(C)CO)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654410]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10843587]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11054840]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	twigs	n.a.	n.a.	PMID[1453182]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15165152]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15165152]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15568770]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15911254]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16392664]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	roots	Hualien Hsien, Taiwan	2003-JUL	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17951038]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18175961]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18348535]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	root	n.a.	PMID[18975262]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19407970]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	bark	n.a.	PMID[21553897]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295087]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24333010]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24459770]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27575476]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30298740]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[9868163]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11523	Erysimum leptophyllum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17849	Centaurea maculosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28072	Theonella conica	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21243	Siphonaria capensis	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4051	Tricholoma columbetta	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21108	Eria anomala	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12313	Haplophyllum obtusifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13449	Syzygium polycephaloides	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16141	Piper regnellii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21562	Diospyros assimilis	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14241	Planchonia grandis	Species	Asterolecaniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17560	Pancratium sickenbergeri	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17258	Rhinella marina	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18866	Pteridium esculentum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19810	Myxococcus stipitatus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9968	Shigella dysenteriae	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21495	Abelia chinensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27367	Latrunculia magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20843	Monsonia senegalensis	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20624	Simarouba glauca	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22961	Cordia leucocephala	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18473	Plathymenia reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19036	Esenbeckia leiocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11795	Plantago stauntoni	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19511	Dolabella californica	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22937	Vernonia fagifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21631	Faramea salicifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21038	Lemaireocereus longispinus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5903	Conus mus	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28202	Helichrysum tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19912	Vellozia nanuzae	Species	Velloziaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20084	Atraphaxis spinosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18143	Dendronephthya griffini	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20421	Aplophyllum alberti-regelii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16569	Gymnocalycium schickendantzii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19995	Baccharis neglecta	Species	Asteraceae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC261245 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	282
0.1-0.2	1992
0.2-0.3	5500
0.3-0.4	10948
0.4-0.5	10876
0.5-0.6	6687
0.6-0.7	3662
0.7-0.8	1846
0.8-0.85	332
0.85-0.9	114
0.9-0.95	337
0.95-1	121

Similarity Score	Similarity Level	Natural Product ID

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 NPC261245 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	2284
0.2-0.3	3889
0.3-0.4	1740
0.4-0.5	564
0.5-0.6	246
0.6-0.7	123
0.7-0.8	35
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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