NPASS Compound

Structure

NPC28811 OpenBabel06302215432D 67 74 0 0 1 0 0 0 0 0999 V2000 -7.5890 -5.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2686 -4.5430 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1968 -4.7917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.8764 -4.1122 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.6277 -3.1839 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6994 -2.9351 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0198 -3.6147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4506 -2.0068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5223 -1.7581 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8428 -2.4377 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0915 -3.3659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4120 -4.0455 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9145 -2.1889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6658 -1.2606 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3453 -0.5811 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2736 -0.8298 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9532 -0.1502 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0966 0.3472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7375 -1.0119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4887 -0.0836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5604 0.1651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3117 1.0934 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3834 1.3422 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7039 0.6626 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9526 -0.2657 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8809 -0.5144 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2730 -0.9452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5835 -0.4478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9427 -1.8069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8323 0.4805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8323 1.4416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6646 1.9221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4969 1.4416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4579 1.4416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9774 2.2738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4969 0.4805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6646 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6646 -0.9610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4969 -1.4416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4969 -2.4026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6646 -2.8831 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6646 -3.8442 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4969 -3.3636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4969 -4.3247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4969 -5.2857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6646 -5.7662 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8323 -5.2857 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1288 -5.2857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3518 -6.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6093 -6.1180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8323 -4.3247 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -3.8442 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.8831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8323 -2.4026 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8323 -1.4416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8323 -1.4416 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.9221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8323 -4.3247 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6646 -6.7273 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7756 0.9113 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1347 2.2705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9913 1.7730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3072 -2.5043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8047 -4.3609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4456 -5.7200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 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 67 1 0 0 0 0 4 5 1 0 0 0 0 4 66 1 0 0 0 0 5 6 1 0 0 0 0 5 65 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 8 9 1 0 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 13 1 0 0 0 0 11 12 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 21 26 1 0 0 0 0 22 23 1 0 0 0 0 22 64 1 0 0 0 0 23 24 1 0 0 0 0 23 63 1 0 0 0 0 24 25 1 0 0 0 0 24 62 1 0 0 0 0 25 26 1 0 0 0 0 25 27 1 0 0 0 0 27 28 1 0 0 0 0 28 29 2 0 0 0 0 28 30 1 0 0 0 0 30 59 1 0 0 0 0 30 31 1 0 0 0 0 30 37 1 0 0 0 0 31 32 1 0 0 0 0 32 33 1 0 0 0 0 33 34 1 0 0 0 0 33 35 1 0 0 0 0 33 36 1 0 0 0 0 36 37 1 0 0 0 0 37 38 1 0 0 0 0 38 56 1 0 0 0 0 38 39 2 0 0 0 0 39 40 1 0 0 0 0 40 41 1 0 0 0 0 41 42 1 0 0 0 0 41 54 1 0 0 0 0 42 51 1 0 0 0 0 42 43 1 6 0 0 0 42 44 1 0 0 0 0 44 45 1 0 0 0 0 45 46 1 0 0 0 0 46 47 1 0 0 0 0 46 61 1 0 0 0 0 47 48 1 6 0 0 0 47 49 1 0 0 0 0 47 51 1 0 0 0 0 49 50 1 0 0 0 0 51 52 1 0 0 0 0 52 53 1 0 0 0 0 52 60 1 0 0 0 0 53 54 1 0 0 0 0 54 55 1 0 0 0 0 54 56 1 0 0 0 0 56 57 1 0 0 0 0 56 58 1 0 0 0 0 58 59 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	958.51
Volume:	932.053
LogP:	1.896
LogD:	1.266
LogS:	-3.252
# Rotatable Bonds:	10
TPSA:	315.21
# H-Bond Aceptor:	19
# H-Bond Donor:	12
# Rings:	8
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.099
Synthetic Accessibility Score:	6.487
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:	-6.164
MDCK Permeability:	0.00011348658154020086
Pgp-inhibitor:	0.059
Pgp-substrate:	0.528
Human Intestinal Absorption (HIA):	0.961
20% Bioavailability (F20%):	0.239
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	60.859596252441406%
Volume Distribution (VD):	0.162
Pgp-substrate:	20.9614315032959%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.431
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.329
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.098
CYP3A4-substrate:	0.009

ADMET: Excretion

Clearance (CL):	0.603
Half-life (T1/2):	0.625

ADMET: Toxicity

hERG Blockers:	0.215
Human Hepatotoxicity (H-HT):	0.213
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.102
Rat Oral Acute Toxicity:	0.107
Maximum Recommended Daily Dose:	0.798
Skin Sensitization:	0.165
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.897

Download Data

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

Natural Product: NPC28811

Natural Product ID:	NPC28811
*Common Name:**	DUQMBNHUHLOXBM-VKJCULEXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DUQMBNHUHLOXBM-VKJCULEXSA-N
Standard InCHI:	InChI=1S/C48H78O19/c1-21-29(53)31(55)34(58)40(63-21)66-37-25(18-49)64-39(36(60)33(37)57)62-19-26-30(54)32(56)35(59)41(65-26)67-42(61)48-14-12-43(2,3)16-23(48)22-8-9-27-44(4)11-10-28(52)45(5,20-50)38(44)24(51)17-47(27,7)46(22,6)13-15-48/h8,21,23-41,49-60H,9-20H2,1-7H3/t21-,23-,24+,25+,26+,27+,28-,29-,30+,31+,32-,33+,34+,35+,36+,37+,38+,39+,40-,41-,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](CO)O[C@H]([C@@H]([C@H]1O)O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=O)[C@@]12CCC(C)(C)C[C@H]2C2=CC[C@@H]3[C@@]4(C)CC[C@@H]([C@@](C)(CO)[C@@H]4[C@@H](C[C@@]3(C)[C@]2(C)CC1)O)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	101103171
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
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]
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]
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]
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]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19276083]
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]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20843794]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22194604]
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]
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]
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]
NPO28576	Berberis julianae	Species	Berberidaceae	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]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	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]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28576	Berberis julianae	Species	Berberidaceae	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]
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]
NPO28011	Swertia japonica	Species	Gentianaceae	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]
NPO28374	Pleogyne cunninghami	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28269	Rubus rosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28073	Crateva nurvala	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28200	Unonopsis glaucopetala	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28656	Lactobacillus casei	Species	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28509	Achillea clypeolata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28303	Pleogyne cunninghamii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16669	Diospyros verrucosa	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28161	Stephania sutchuenensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28704	Agaricus hortensis	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28691	Streptomyces odorifer	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27867	Turbo argyrostoma	Species	Turbinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27990	Schizonepeta multifida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28131	Polygala amara	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28481	Cerbera dilatata	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]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27943	Cardamine pinnata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29115	Rhinella arenarum	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20395	Athanasia crithmifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28614	Zieria smithii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27959	Codonocarpus australis	Species	Gyrostemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28053	Quercus serrata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28596	Streptomyces lavendofoliae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28035	Streptomyces fumanus	Species	Streptomycetaceae	Bacteria	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]
NPO28633	Bystropogon origanifolius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28670	Mortierella elongata	Species	Mortierellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6331	Jacobaea subalpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28391	Euonymus nanoides	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25704	Tetraneuris acaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	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 NPC28811 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	261
0.1-0.2	1737
0.2-0.3	5108
0.3-0.4	11934
0.4-0.5	10269
0.5-0.6	6164
0.6-0.7	3984
0.7-0.8	1930
0.8-0.85	607
0.85-0.9	291
0.9-0.95	169
0.95-1	243

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 NPC28811 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	2042
0.2-0.3	3876
0.3-0.4	1952
0.4-0.5	598
0.5-0.6	266
0.6-0.7	142
0.7-0.8	21
0.8-0.85	8
0.85-0.9	3
0.9-0.95	1
0.95-1	0

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