NPASS Compound

Structure

NPC216199 OpenBabel06302215592D 42 43 0 0 1 0 0 0 0 0999 V2000 -5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.5885 -9.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -15.5885 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.2224 -6.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.2224 -6.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.4545 -9.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 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 2 1 0 0 0 0 2 3 2 0 0 0 0 2 26 1 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 6 7 2 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 14 15 3 0 0 0 0 15 16 1 0 0 0 0 16 22 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 20 25 1 1 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 26 27 2 0 0 0 0 27 28 1 0 0 0 0 28 29 2 0 0 0 0 29 30 1 0 0 0 0 29 31 1 0 0 0 0 31 32 3 0 0 0 0 32 33 1 0 0 0 0 33 39 1 0 0 0 0 33 34 2 0 0 0 0 34 35 1 0 0 0 0 34 36 1 0 0 0 0 36 37 1 0 0 0 0 37 38 1 0 0 0 0 37 42 1 6 0 0 0 38 39 1 0 0 0 0 39 40 1 0 0 0 0 39 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	564.4
Volume:	666.589
LogP:	6.713
LogD:	5.125
LogS:	-5.46
# Rotatable Bonds:	6
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.249
Synthetic Accessibility Score:	4.966
Fsp3:	0.45
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-5.216
MDCK Permeability:	1.4399806786968838e-05
Pgp-inhibitor:	0.056
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	102.71393585205078%
Volume Distribution (VD):	3.931
Pgp-substrate:	1.6136832237243652%

ADMET: Metabolism

CYP1A2-inhibitor:	0.515
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.921
CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.937
CYP2C9-substrate:	0.998
CYP2D6-inhibitor:	0.968
CYP2D6-substrate:	0.963
CYP3A4-inhibitor:	0.979
CYP3A4-substrate:	0.871

ADMET: Excretion

Clearance (CL):	3.937
Half-life (T1/2):	0.005

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.218
AMES Toxicity:	0.057
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.942
Carcinogencity:	0.538
Eye Corrosion:	0.229
Eye Irritation:	0.174
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC216199

Natural Product ID:	NPC216199
*Common Name:**	DVICWXUADSCSLL-DDEWRDOISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DVICWXUADSCSLL-DDEWRDOISA-N
Standard InCHI:	InChI=1S/C40H52O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-20,35-36,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,29-15+,30-16+,31-19+,32-20+/t35-,36-/m1/s1
SMILES:	C/C(=CC=CC=C(/C)C=CC=C(/C)C#CC1=C(C)C[C@H](CC1(C)C)O)/C=C/C=C(C)/C#CC1=C(C)C[C@H](CC1(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	6443740
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO21005	Baphia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(92)80059-N]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	DOI[10.1016/S0040-4039(00)86970-1]
NPO4343	Guanomyces polythrix	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[10869195]
NPO17256	Kobresia nepalensis	Species	Cyperaceae	Eukaryota	n.a.	stem	n.a.	PMID[16508191]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17340534]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	skin-removed stems	Pingle Town, Sichuang Province, China	2008-AUG	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	stem	n.a.	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22690646]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[23397723]
NPO20739	Jungermannia hyalina	Species	Jungermanniaceae	Eukaryota	n.a.	Guangxi Zhuang Autonomous Region, China	n.a.	PMID[25856683]
NPO21618	Ircinia oros	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28840725]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31182315]
NPO20212	Callistemon viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31276403]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3430163]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[3760884]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6736970]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6875576]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6875577]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	PMID[6875577]
NPO20671	Selliguea feei	Species	Polypodiaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[8254348]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO23343	Cynara cardunculus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8650.1	Perilla frutescens var. arguta	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1663	Amberboa muricata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23343	Cynara cardunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19488	Trifolium subterraneum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO17256	Kobresia nepalensis	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8678	Trillium camschatcense	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1663	Amberboa muricata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8650.1	Perilla frutescens var. arguta	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19488	Trifolium subterraneum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11966	Euphorbia kamerunica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9635	Fenneropenaeus orientalis	Species	Penaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23343	Cynara cardunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23343	Cynara cardunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1663	Amberboa muricata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20612	Ursinia abrotanifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4031.1	Cynara cardunculus var. scolymus	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16044	Cupressus lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19488	Trifolium subterraneum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11966	Euphorbia kamerunica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20212	Callistemon viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13260	Eria foetida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20739	Jungermannia hyalina	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19773	Xenorhabdus bovienii	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21005	Baphia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1663	Amberboa muricata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20872	Melampodium heterophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21550	Achillea macrophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8678	Trillium camschatcense	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22510	Eupatorium havanense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17256	Kobresia nepalensis	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20340	Pausinystalia mayumbensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20408	Ajuga spectabilis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14466	Penicillium olsonii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21231	Astragalus tragacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21426	Alstroemeria revoluta	Species	Alstroemeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21486	Marrubium alysson	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18096	Excoecaria oppositifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19622	Euphorbia marginata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27626	Limonia acidissima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26840	Litsea aciculata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20671	Selliguea feei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21088	Litsea pulchella	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2854	Gymnosporia senegalensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21365	Ligularia muliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20546	Cissus pallidiflorus	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20813	Myrmica sabuleti	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17515	Pronephrium triphyllum	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3777	Stevia chamaedrys	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21289	Teucrium oxylepis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19986	Crataegus davisii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8650.1	Perilla frutescens var. arguta	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11622.1	Shuteria involucrata var. vestita	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3237	Mytilus edulis	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21618	Ircinia oros	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16907	Pentzia incana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15216	Encephalartos altensteinii	Species	Zamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9635	Fenneropenaeus orientalis	Species	Penaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4343	Guanomyces polythrix	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20051	Gardenia collinsae	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14136	Acherontia atropus	Species	Sphingidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14330	Agave aurea	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16454	Crinum erubescens	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18620	Grindelia acutifolia	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 NPC216199 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	165
0.1-0.2	1559
0.2-0.3	11914
0.3-0.4	16260
0.4-0.5	8681
0.5-0.6	3421
0.6-0.7	664
0.7-0.8	29
0.8-0.85	0
0.85-0.9	3
0.9-0.95	1
0.95-1	0

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 NPC216199 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	2020
0.2-0.3	4405
0.3-0.4	1953
0.4-0.5	464
0.5-0.6	103
0.6-0.7	45
0.7-0.8	3
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
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