NPASS Compound

Structure

CID18536 OpenBabel06191715342D 35 40 0 0 1 0 0 0 0 0999 V2000 0.7179 1.2645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8109 2.0151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5084 4.8182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4797 2.0045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6453 0.7648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6453 3.2549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9204 0.3357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1955 -0.0828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8201 2.8469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8201 3.6839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0951 1.5913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1955 2.4284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3702 1.1728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9204 2.8469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8161 1.6947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3702 3.6839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8162 -0.1863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6248 0.8564 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9204 1.1728 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4706 1.1728 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3702 2.8469 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.5084 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6819 4.8182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0951 2.4284 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0951 4.1025 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1955 1.5913 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6453 1.5913 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6453 2.4284 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4706 0.3357 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3633 0.7542 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5188 2.1589 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0951 5.5340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8554 4.8182 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1941 0.7084 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 18 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 9 10 1 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 20 1 0 0 0 0 15 22 1 0 0 0 0 16 21 1 0 0 0 0 16 25 1 0 0 0 0 17 29 1 0 0 0 0 17 35 1 0 0 0 0 18 29 1 6 0 0 0 18 30 1 0 0 0 0 19 26 1 1 0 0 0 19 27 1 0 0 0 0 20 26 1 1 0 0 0 20 29 1 0 0 0 0 21 24 1 6 0 0 0 21 28 1 0 0 0 0 22 30 1 6 0 0 0 22 31 1 0 0 0 0 23 25 1 0 0 0 0 23 32 2 0 0 0 0 23 33 1 0 0 0 0 24 2 1 1 0 0 0 25 3 1 1 0 0 0 26 4 1 1 0 0 0 27 28 1 1 0 0 0 28 6 1 6 0 0 0 29 8 1 6 0 0 0 30 34 1 6 0 0 0 30 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.35
Volume:	517.412
LogP:	4.082
LogD:	3.586
LogS:	-4.448
# Rotatable Bonds:	1
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.446
Synthetic Accessibility Score:	6.443
Fsp3:	0.967
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.437
MDCK Permeability:	2.197980575147085e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.054
30% Bioavailability (F30%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.371
Plasma Protein Binding (PPB):	92.25418090820312%
Volume Distribution (VD):	0.75
Pgp-substrate:	5.614920616149902%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.626
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.782
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.171
CYP3A4-substrate:	0.151

ADMET: Excretion

Clearance (CL):	1.603
Half-life (T1/2):	0.405

ADMET: Toxicity

hERG Blockers:	0.202
Human Hepatotoxicity (H-HT):	0.547
Drug-inuced Liver Injury (DILI):	0.083
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.877
Carcinogencity:	0.119
Eye Corrosion:	0.004
Eye Irritation:	0.132
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC18536

Natural Product ID:	NPC18536
*Common Name:**	Orthosphenic Acid
IUPAC Name:	n.a.
Synonyms:	Orthosphenic Acid
Standard InCHIKey:	JPAXVSRGFJVPEU-XCIUXINDSA-N
Standard InCHI:	InChI=1S/C30H48O5/c1-18-29-8-7-19-26(4,20(29)15-22(31)30(18,34)35-17-29)12-14-28(6)21-16-25(3,23(32)33)10-9-24(21,2)11-13-27(19,28)5/h18-22,31,34H,7-17H2,1-6H3,(H,32,33)/t18-,19+,20+,21-,22-,24-,25-,26-,27-,28+,29+,30-/m1/s1
SMILES:	O[C@@H]1C[C@@H]2[C@@]3([C@H]([C@@]1(O)OC3)C)CC[C@H]1[C@@]2(C)CC[C@@]2([C@]1(C)CC[C@@]1([C@H]2C[C@@](C)(CC1)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515079
PubChem CID:	20056194
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(90)85349-K]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1186/1471-2202-6-1]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579865]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[10716597]
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10757717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374948]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11561442]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12579877]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[12943781]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951446]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1375626]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	stems	Thailand	n.a.	PMID[14510595]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	Argentine	n.a.	PMID[14738381]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738381]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[16864458]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[16989518]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17250858]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17265278]
NPO1207	Microtropis triflora	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17972583]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18554602]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[18996177]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[20167482]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	root	n.a.	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21514608]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21905650]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	dried roots	purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China)	n.a.	PMID[22148431]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[23268606]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23852638]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24549173]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24697288]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24963543]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25237706]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[2534610]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[27113553]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[2801129]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[2816380]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29355322]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31556299]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32998509]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7102323]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7304185]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699928]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8722541]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[9599285]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10247	Orthosphenia mexicana	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15272	Mascarenhasia arborescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9780	Merremia umbellata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12680	Perityle vaseyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5078	Turraeanthus mannii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15858	Phoebe formosana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15015	Meconopsis napaulensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16428	Millettia conraui	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15393	Eucalyptus flocktoniae	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12555	Aspergillus quadrilineatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13375	Palafoxia rosea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26017	Dalbergia stipulacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24732	Cereus weberi	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14218	Spodoptera littoralis	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15138	Rheum webbianum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16516	Centaurea seridis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4935	Dinemasporium strigosum	Species	Chaetosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4267	Ceratocystis clavigera	Species	Ceratocystidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16758	Satureja cuneifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13548	Chrozophora obliqua	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15755	Thymbra spicata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5269	Coleus garckeanus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10247	Orthosphenia mexicana	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1207	Microtropis triflora	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8499	Osmerus mordax	Species	Osmeridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11194	Bombus hortorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13859	Senecio flavus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11881	Adenopeltis colliguaya	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5552	Solanum sisymbriifolium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14034	Salvia coulteri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16175	Trichia floriformis	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13230	Pedicularis condensata	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16678	Flindersia brayleyana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11599	Elaeagnus commutata	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13710	Lyophyllum shimeji	Species	Lyophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3391	Jungermannia obovata	Species	Jungermanniaceae	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

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	>	100000.0	nM	PMID[503780]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	Inhibition	=	19.0	%	PMID[503780]

☑ 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 NPC18536 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	429
0.1-0.2	3254
0.2-0.3	8830
0.3-0.4	14004
0.4-0.5	6280
0.5-0.6	4687
0.6-0.7	3145
0.7-0.8	1801
0.8-0.85	198
0.85-0.9	55
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC50443
0.9121	High Similarity	NPC472145
0.9091	High Similarity	NPC185529
0.9091	High Similarity	NPC472146
0.9022	High Similarity	NPC472144
0.8929	High Similarity	NPC474870
0.8929	High Similarity	NPC271572
0.8837	High Similarity	NPC473299
0.8804	High Similarity	NPC235109
0.8696	High Similarity	NPC82633
0.8602	High Similarity	NPC475785
0.8602	High Similarity	NPC163685
0.8506	High Similarity	NPC269684
0.8488	Intermediate Similarity	NPC280781
0.8488	Intermediate Similarity	NPC48756
0.8462	Intermediate Similarity	NPC470114
0.8444	Intermediate Similarity	NPC476379
0.8404	Intermediate Similarity	NPC475765
0.8391	Intermediate Similarity	NPC208912
0.8391	Intermediate Similarity	NPC2096
0.8391	Intermediate Similarity	NPC121121
0.8384	Intermediate Similarity	NPC126753
0.8353	Intermediate Similarity	NPC243594
0.8353	Intermediate Similarity	NPC472608
0.8353	Intermediate Similarity	NPC31031
0.8352	Intermediate Similarity	NPC67653
0.8352	Intermediate Similarity	NPC471459
0.8351	Intermediate Similarity	NPC80640
0.8333	Intermediate Similarity	NPC80417
0.8316	Intermediate Similarity	NPC471241
0.8316	Intermediate Similarity	NPC472273
0.8315	Intermediate Similarity	NPC62572
0.83	Intermediate Similarity	NPC207693
0.8295	Intermediate Similarity	NPC474284
0.8295	Intermediate Similarity	NPC475820
0.8295	Intermediate Similarity	NPC474346
0.8295	Intermediate Similarity	NPC474253
0.8295	Intermediate Similarity	NPC213737
0.828	Intermediate Similarity	NPC472148
0.828	Intermediate Similarity	NPC472147
0.8276	Intermediate Similarity	NPC476071
0.8242	Intermediate Similarity	NPC476435
0.8218	Intermediate Similarity	NPC22709
0.8202	Intermediate Similarity	NPC237938
0.8202	Intermediate Similarity	NPC219535
0.8182	Intermediate Similarity	NPC469827
0.8182	Intermediate Similarity	NPC267637
0.8172	Intermediate Similarity	NPC475878
0.8144	Intermediate Similarity	NPC51579
0.8137	Intermediate Similarity	NPC470622
0.8137	Intermediate Similarity	NPC471431
0.8132	Intermediate Similarity	NPC470920
0.8111	Intermediate Similarity	NPC131350
0.81	Intermediate Similarity	NPC119628
0.81	Intermediate Similarity	NPC158367
0.81	Intermediate Similarity	NPC184805
0.81	Intermediate Similarity	NPC273189
0.81	Intermediate Similarity	NPC158051
0.8061	Intermediate Similarity	NPC477172
0.8046	Intermediate Similarity	NPC201276
0.8046	Intermediate Similarity	NPC73013
0.8046	Intermediate Similarity	NPC80891
0.8043	Intermediate Similarity	NPC471221
0.8041	Intermediate Similarity	NPC471374
0.8041	Intermediate Similarity	NPC471375
0.8041	Intermediate Similarity	NPC209798
0.8039	Intermediate Similarity	NPC240125
0.8039	Intermediate Similarity	NPC91583
0.8022	Intermediate Similarity	NPC471410
0.8022	Intermediate Similarity	NPC83242
0.8022	Intermediate Similarity	NPC471411
0.8021	Intermediate Similarity	NPC256227
0.8021	Intermediate Similarity	NPC116683
0.802	Intermediate Similarity	NPC475630
0.802	Intermediate Similarity	NPC475234
0.802	Intermediate Similarity	NPC40716
0.802	Intermediate Similarity	NPC138219
0.802	Intermediate Similarity	NPC471430
0.8	Intermediate Similarity	NPC25037
0.8	Intermediate Similarity	NPC473336
0.8	Intermediate Similarity	NPC34984
0.8	Intermediate Similarity	NPC100078
0.8	Intermediate Similarity	NPC471044
0.8	Intermediate Similarity	NPC18953
0.7981	Intermediate Similarity	NPC157571
0.798	Intermediate Similarity	NPC470172
0.7978	Intermediate Similarity	NPC477446
0.7978	Intermediate Similarity	NPC470155
0.7978	Intermediate Similarity	NPC61107
0.7978	Intermediate Similarity	NPC289486
0.7978	Intermediate Similarity	NPC477447
0.7959	Intermediate Similarity	NPC471426
0.7959	Intermediate Similarity	NPC471428
0.7959	Intermediate Similarity	NPC471427
0.7955	Intermediate Similarity	NPC472943
0.7955	Intermediate Similarity	NPC472951
0.7955	Intermediate Similarity	NPC261616
0.7941	Intermediate Similarity	NPC473688
0.7941	Intermediate Similarity	NPC469826
0.7941	Intermediate Similarity	NPC262567
0.7941	Intermediate Similarity	NPC285576
0.7941	Intermediate Similarity	NPC471626
0.7941	Intermediate Similarity	NPC231566
0.7941	Intermediate Similarity	NPC88744
0.7935	Intermediate Similarity	NPC213658
0.7935	Intermediate Similarity	NPC110365
0.7935	Intermediate Similarity	NPC45833
0.7935	Intermediate Similarity	NPC239938
0.7935	Intermediate Similarity	NPC62202
0.7931	Intermediate Similarity	NPC224802
0.7931	Intermediate Similarity	NPC171426
0.7931	Intermediate Similarity	NPC324700
0.7931	Intermediate Similarity	NPC34046
0.7931	Intermediate Similarity	NPC26029
0.7931	Intermediate Similarity	NPC80089
0.7921	Intermediate Similarity	NPC166079
0.7917	Intermediate Similarity	NPC215570
0.7917	Intermediate Similarity	NPC94582
0.7917	Intermediate Similarity	NPC57964
0.7912	Intermediate Similarity	NPC478111
0.79	Intermediate Similarity	NPC225238
0.79	Intermediate Similarity	NPC473406
0.7895	Intermediate Similarity	NPC291373
0.7895	Intermediate Similarity	NPC475307
0.7895	Intermediate Similarity	NPC211845
0.7895	Intermediate Similarity	NPC122083
0.7895	Intermediate Similarity	NPC256104
0.7895	Intermediate Similarity	NPC182740
0.7889	Intermediate Similarity	NPC111582
0.7889	Intermediate Similarity	NPC477285
0.7872	Intermediate Similarity	NPC77756
0.7865	Intermediate Similarity	NPC470156
0.7865	Intermediate Similarity	NPC470154
0.7865	Intermediate Similarity	NPC475743
0.7865	Intermediate Similarity	NPC50658
0.7865	Intermediate Similarity	NPC73515
0.7864	Intermediate Similarity	NPC154906
0.7864	Intermediate Similarity	NPC469825
0.7864	Intermediate Similarity	NPC473844
0.7864	Intermediate Similarity	NPC51947
0.7864	Intermediate Similarity	NPC87393
0.7849	Intermediate Similarity	NPC3032
0.7849	Intermediate Similarity	NPC473319
0.7849	Intermediate Similarity	NPC131104
0.7843	Intermediate Similarity	NPC203974
0.7835	Intermediate Similarity	NPC238796
0.7835	Intermediate Similarity	NPC203434
0.7835	Intermediate Similarity	NPC237071
0.7835	Intermediate Similarity	NPC476728
0.783	Intermediate Similarity	NPC477465
0.7826	Intermediate Similarity	NPC215968
0.7826	Intermediate Similarity	NPC80700
0.7826	Intermediate Similarity	NPC472272
0.7826	Intermediate Similarity	NPC155531
0.7816	Intermediate Similarity	NPC317913
0.7816	Intermediate Similarity	NPC298168
0.7816	Intermediate Similarity	NPC207010
0.7816	Intermediate Similarity	NPC143133
0.7812	Intermediate Similarity	NPC277399
0.7802	Intermediate Similarity	NPC477434
0.7802	Intermediate Similarity	NPC105895
0.7802	Intermediate Similarity	NPC79308
0.78	Intermediate Similarity	NPC471254
0.78	Intermediate Similarity	NPC244969
0.78	Intermediate Similarity	NPC213528
0.7788	Intermediate Similarity	NPC199457
0.7788	Intermediate Similarity	NPC68419
0.7788	Intermediate Similarity	NPC66513
0.7788	Intermediate Similarity	NPC108709
0.7788	Intermediate Similarity	NPC110139
0.7788	Intermediate Similarity	NPC75747
0.7788	Intermediate Similarity	NPC7870
0.7788	Intermediate Similarity	NPC102914
0.7778	Intermediate Similarity	NPC100366
0.7778	Intermediate Similarity	NPC242771
0.7778	Intermediate Similarity	NPC41843
0.7778	Intermediate Similarity	NPC311642
0.7778	Intermediate Similarity	NPC60018
0.7778	Intermediate Similarity	NPC20028
0.7778	Intermediate Similarity	NPC154043
0.7778	Intermediate Similarity	NPC202688
0.7778	Intermediate Similarity	NPC477286
0.7778	Intermediate Similarity	NPC164289
0.7778	Intermediate Similarity	NPC286719
0.7767	Intermediate Similarity	NPC472079
0.7765	Intermediate Similarity	NPC68426
0.7765	Intermediate Similarity	NPC282905
0.7765	Intermediate Similarity	NPC477229
0.7755	Intermediate Similarity	NPC470425
0.7753	Intermediate Similarity	NPC475456
0.7745	Intermediate Similarity	NPC477877
0.7745	Intermediate Similarity	NPC306776
0.7736	Intermediate Similarity	NPC97002
0.7732	Intermediate Similarity	NPC305808
0.7727	Intermediate Similarity	NPC252483
0.7727	Intermediate Similarity	NPC191345
0.7723	Intermediate Similarity	NPC471253
0.7723	Intermediate Similarity	NPC107385
0.7717	Intermediate Similarity	NPC476715
0.7717	Intermediate Similarity	NPC266651

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 NPC18536 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	453
0.1-0.2	3455
0.2-0.3	3469
0.3-0.4	1054
0.4-0.5	392
0.5-0.6	231
0.6-0.7	74
0.7-0.8	21
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7931	Intermediate Similarity	NPD6697	Approved
0.7931	Intermediate Similarity	NPD6118	Approved
0.7931	Intermediate Similarity	NPD6115	Approved
0.7931	Intermediate Similarity	NPD6114	Approved
0.7816	Intermediate Similarity	NPD6116	Phase 1
0.7701	Intermediate Similarity	NPD6117	Approved
0.7647	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD8133	Approved
0.7245	Intermediate Similarity	NPD8035	Phase 2
0.7245	Intermediate Similarity	NPD8034	Phase 2
0.7207	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD3703	Phase 2
0.7174	Intermediate Similarity	NPD6928	Phase 2
0.7172	Intermediate Similarity	NPD8171	Discontinued
0.7158	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6940	Discontinued
0.6944	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7748	Approved
0.69	Remote Similarity	NPD7515	Phase 2
0.6893	Remote Similarity	NPD7902	Approved
0.6881	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5777	Approved
0.6838	Remote Similarity	NPD8328	Phase 3
0.6771	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD3669	Approved
0.6742	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4244	Approved
0.6742	Remote Similarity	NPD4245	Approved
0.6737	Remote Similarity	NPD1780	Approved
0.6737	Remote Similarity	NPD1779	Approved
0.6697	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6081	Approved
0.6667	Remote Similarity	NPD4224	Phase 2
0.6667	Remote Similarity	NPD7638	Approved
0.6636	Remote Similarity	NPD6686	Approved
0.663	Remote Similarity	NPD3702	Approved
0.6629	Remote Similarity	NPD3698	Phase 2
0.6629	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7640	Approved
0.6604	Remote Similarity	NPD7639	Approved
0.6602	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7900	Approved
0.6583	Remote Similarity	NPD7507	Approved
0.6556	Remote Similarity	NPD4789	Approved
0.6542	Remote Similarity	NPD1700	Approved
0.6518	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5360	Phase 3
0.6481	Remote Similarity	NPD7632	Discontinued
0.6475	Remote Similarity	NPD7736	Approved
0.6449	Remote Similarity	NPD8418	Phase 2
0.6423	Remote Similarity	NPD7319	Approved
0.6421	Remote Similarity	NPD3671	Phase 1
0.6364	Remote Similarity	NPD7492	Approved
0.6364	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD7516	Approved
0.6348	Remote Similarity	NPD4632	Approved
0.6346	Remote Similarity	NPD6399	Phase 3
0.6344	Remote Similarity	NPD1811	Approved
0.6344	Remote Similarity	NPD1810	Approved
0.6325	Remote Similarity	NPD6009	Approved
0.6311	Remote Similarity	NPD6616	Approved
0.6303	Remote Similarity	NPD6054	Approved
0.6303	Remote Similarity	NPD8377	Approved
0.6303	Remote Similarity	NPD6059	Approved
0.6303	Remote Similarity	NPD8294	Approved
0.6271	Remote Similarity	NPD7328	Approved
0.6271	Remote Similarity	NPD7327	Approved
0.626	Remote Similarity	NPD7078	Approved
0.626	Remote Similarity	NPD8293	Discontinued
0.625	Remote Similarity	NPD8335	Approved
0.625	Remote Similarity	NPD8296	Approved
0.625	Remote Similarity	NPD8380	Approved
0.625	Remote Similarity	NPD6921	Approved
0.625	Remote Similarity	NPD8378	Approved
0.625	Remote Similarity	NPD8379	Approved
0.625	Remote Similarity	NPD371	Approved
0.625	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8033	Approved
0.6226	Remote Similarity	NPD7991	Discontinued
0.6198	Remote Similarity	NPD6370	Approved
0.6167	Remote Similarity	NPD6319	Approved
0.6161	Remote Similarity	NPD7128	Approved
0.6161	Remote Similarity	NPD5739	Approved
0.6161	Remote Similarity	NPD6675	Approved
0.6161	Remote Similarity	NPD6402	Approved
0.6148	Remote Similarity	NPD6067	Discontinued
0.6129	Remote Similarity	NPD4758	Discontinued
0.6121	Remote Similarity	NPD6882	Approved
0.6121	Remote Similarity	NPD8297	Approved
0.6116	Remote Similarity	NPD6016	Approved
0.6116	Remote Similarity	NPD6015	Approved
0.6082	Remote Similarity	NPD4802	Phase 2
0.6082	Remote Similarity	NPD5364	Discontinued
0.6082	Remote Similarity	NPD4238	Approved
0.6067	Remote Similarity	NPD7909	Approved
0.6066	Remote Similarity	NPD5988	Approved
0.6055	Remote Similarity	NPD4225	Approved
0.6053	Remote Similarity	NPD6899	Approved
0.6053	Remote Similarity	NPD6881	Approved
0.6053	Remote Similarity	NPD7320	Approved
0.605	Remote Similarity	NPD7115	Discovery
0.6022	Remote Similarity	NPD2254	Approved
0.6022	Remote Similarity	NPD2686	Approved
0.6022	Remote Similarity	NPD2687	Approved
0.602	Remote Similarity	NPD7645	Phase 2
0.6018	Remote Similarity	NPD6008	Approved
0.6016	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5984	Remote Similarity	NPD7503	Approved
0.5984	Remote Similarity	NPD8517	Approved
0.5984	Remote Similarity	NPD8516	Approved
0.5984	Remote Similarity	NPD8515	Approved
0.5984	Remote Similarity	NPD5983	Phase 2
0.5984	Remote Similarity	NPD8513	Phase 3
0.5965	Remote Similarity	NPD5697	Approved
0.5965	Remote Similarity	NPD5701	Approved
0.5962	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD6033	Approved
0.5952	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD7102	Approved
0.5948	Remote Similarity	NPD7290	Approved
0.5948	Remote Similarity	NPD6883	Approved
0.5922	Remote Similarity	NPD3618	Phase 1
0.592	Remote Similarity	NPD6336	Discontinued
0.5913	Remote Similarity	NPD6011	Approved
0.5905	Remote Similarity	NPD5328	Approved
0.5897	Remote Similarity	NPD6847	Approved
0.5897	Remote Similarity	NPD8130	Phase 1
0.5897	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6649	Approved
0.5897	Remote Similarity	NPD6869	Approved
0.5897	Remote Similarity	NPD6617	Approved
0.5897	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6650	Approved
0.5882	Remote Similarity	NPD4786	Approved
0.5862	Remote Similarity	NPD6012	Approved
0.5862	Remote Similarity	NPD6014	Approved
0.5862	Remote Similarity	NPD6013	Approved
0.5851	Remote Similarity	NPD4787	Phase 1
0.5842	Remote Similarity	NPD3667	Approved
0.5818	Remote Similarity	NPD6084	Phase 2
0.5818	Remote Similarity	NPD6083	Phase 2
0.5806	Remote Similarity	NPD229	Approved
0.58	Remote Similarity	NPD7525	Registered
0.5795	Remote Similarity	NPD3198	Approved
0.5794	Remote Similarity	NPD6079	Approved
0.5789	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD4788	Approved
0.5769	Remote Similarity	NPD7521	Approved
0.5769	Remote Similarity	NPD7334	Approved
0.5769	Remote Similarity	NPD6684	Approved
0.5769	Remote Similarity	NPD5330	Approved
0.5769	Remote Similarity	NPD6409	Approved
0.5769	Remote Similarity	NPD7146	Approved
0.5765	Remote Similarity	NPD3730	Approved
0.5765	Remote Similarity	NPD3728	Approved
0.5755	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD4202	Approved
0.5739	Remote Similarity	NPD6920	Discontinued
0.5678	Remote Similarity	NPD4634	Approved
0.5676	Remote Similarity	NPD4755	Approved
0.5667	Remote Similarity	NPD8298	Phase 2
0.566	Remote Similarity	NPD6903	Approved
0.566	Remote Similarity	NPD5737	Approved
0.566	Remote Similarity	NPD6672	Approved
0.5648	Remote Similarity	NPD6411	Approved
0.5641	Remote Similarity	NPD8174	Phase 2
0.5636	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD8138	Approved
0.5614	Remote Similarity	NPD8084	Approved
0.5614	Remote Similarity	NPD8083	Approved
0.5614	Remote Similarity	NPD8085	Approved
0.5614	Remote Similarity	NPD8139	Approved
0.5614	Remote Similarity	NPD8082	Approved
0.5614	Remote Similarity	NPD8086	Approved
0.561	Remote Similarity	NPD6335	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