NPASS Compound

Structure

CID230387 OpenBabel06191716022D 32 36 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 1.7321 3.0000 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 -0.0000 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 0.8660 -0.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 16 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 20 1 0 0 0 0 9 11 1 0 0 0 0 9 25 1 0 0 0 0 10 12 1 0 0 0 0 10 26 1 0 0 0 0 11 28 1 0 0 0 0 12 27 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 15 1 1 1 0 0 0 15 22 1 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 18 25 1 1 0 0 0 19 23 1 0 0 0 0 19 29 1 1 0 0 0 20 25 1 1 0 0 0 20 27 1 0 0 0 0 21 26 1 6 0 0 0 21 28 1 0 0 0 0 22 24 1 0 0 0 0 22 30 2 0 0 0 0 23 31 2 0 0 0 0 24 26 1 1 0 0 0 24 32 1 0 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 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.31
Volume:	477.313
LogP:	4.302
LogD:	3.6
LogS:	-4.315
# Rotatable Bonds:	0
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.536
Synthetic Accessibility Score:	5.056
Fsp3:	0.893
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.891
MDCK Permeability:	1.60256058734376e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.432

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.563
Plasma Protein Binding (PPB):	95.18696594238281%
Volume Distribution (VD):	0.666
Pgp-substrate:	3.3653645515441895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.636
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.864
CYP2C9-inhibitor:	0.112
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.746
CYP3A4-substrate:	0.657

ADMET: Excretion

Clearance (CL):	11.938
Half-life (T1/2):	0.199

ADMET: Toxicity

hERG Blockers:	0.486
Human Hepatotoxicity (H-HT):	0.531
Drug-inuced Liver Injury (DILI):	0.738
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.722
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.613
Carcinogencity:	0.31
Eye Corrosion:	0.055
Eye Irritation:	0.015
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: NPC230387

Natural Product ID:	NPC230387
*Common Name:**	Triptocalline A
IUPAC Name:	(2R,4S,4aR,6aS,6aR,6bS,11S,12aS,14aS,14bS)-4,11-dihydroxy-2,4a,6a,6a,9,14a-hexamethyl-1,2,4,5,6,6b,7,8,11,12,12a,13,14,14b-tetradecahydropicene-3,10-dione
Synonyms:
Standard InCHIKey:	UUGCGHAFZPEHIC-OIOGIDCRSA-N
Standard InCHI:	InChI=1S/C28H42O4/c1-15-13-21-26(4,24(32)22(15)30)10-12-27(5)20-8-7-17-16(2)23(31)19(29)14-18(17)25(20,3)9-11-28(21,27)6/h15,18-21,24,29,32H,7-14H2,1-6H3/t15-,18-,19+,20+,21-,24-,25+,26-,27-,28+/m1/s1
SMILES:	C[C@@H]1C[C@@H]2[C@@]([C@@H](C1=O)O)(C)CC[C@]1([C@@]2(C)CC[C@@]2([C@@H]1CCC1=C(C(=O)[C@H](C[C@@H]21)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452498
PubChem CID:	44559634
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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.	n.a.	n.a.	PMID[14738381]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	Argentine	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]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	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]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	root	n.a.	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	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]
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.	n.a.	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5728	Gerbera piloselloides	Species	Asteraceae	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]
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]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15961	Sida cordifolia	Species	Malvaceae	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]
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]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3391	Jungermannia obovata	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12680	Perityle vaseyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15272	Mascarenhasia arborescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5078	Turraeanthus mannii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15510	Kummerowia striata	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]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16428	Millettia conraui	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13375	Palafoxia rosea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9780	Merremia umbellata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26017	Dalbergia stipulacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24732	Cereus weberi	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15858	Phoebe formosana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14218	Spodoptera littoralis	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15138	Rheum webbianum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15015	Meconopsis napaulensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16516	Centaurea seridis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4267	Ceratocystis clavigera	Species	Ceratocystidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12555	Aspergillus quadrilineatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16758	Satureja cuneifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4935	Dinemasporium strigosum	Species	Chaetosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23289	Heracleum sphondylium	Species	Apiaceae	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]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5269	Coleus garckeanus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11194	Bombus hortorum	Species	Apidae	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]
NPO5552	Solanum sisymbriifolium	Species	Solanaceae	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]
NPO16175	Trichia floriformis	Species	Trichiidae	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]
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]
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]
NPO5728	Gerbera piloselloides	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

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	14000.0	nM	PMID[542323]

☑ 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 NPC230387 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	228
0.1-0.2	1680
0.2-0.3	6144
0.3-0.4	15151
0.4-0.5	8138
0.5-0.6	5427
0.6-0.7	4498
0.7-0.8	1108
0.8-0.85	247
0.85-0.9	70
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9205	High Similarity	NPC23170
0.9091	High Similarity	NPC211230
0.8989	High Similarity	NPC474328
0.8977	High Similarity	NPC158030
0.8977	High Similarity	NPC233455
0.8977	High Similarity	NPC65120
0.8977	High Similarity	NPC4036
0.8977	High Similarity	NPC145067
0.8977	High Similarity	NPC474525
0.8953	High Similarity	NPC73064
0.8941	High Similarity	NPC133954
0.8876	High Similarity	NPC295643
0.8876	High Similarity	NPC214756
0.8876	High Similarity	NPC272075
0.8864	High Similarity	NPC46441
0.8837	High Similarity	NPC475862
0.8837	High Similarity	NPC158393
0.8837	High Similarity	NPC213412
0.8837	High Similarity	NPC74363
0.8837	High Similarity	NPC471737
0.8837	High Similarity	NPC56588
0.8824	High Similarity	NPC180834
0.8795	High Similarity	NPC18955
0.8791	High Similarity	NPC157113
0.8791	High Similarity	NPC62516
0.875	High Similarity	NPC143232
0.875	High Similarity	NPC274330
0.875	High Similarity	NPC122116
0.875	High Similarity	NPC198664
0.8721	High Similarity	NPC197823
0.869	High Similarity	NPC328264
0.8681	High Similarity	NPC139570
0.8681	High Similarity	NPC148523
0.8652	High Similarity	NPC470589
0.8652	High Similarity	NPC126369
0.8652	High Similarity	NPC111110
0.8652	High Similarity	NPC291028
0.8636	High Similarity	NPC17733
0.8636	High Similarity	NPC206060
0.8636	High Similarity	NPC474512
0.8636	High Similarity	NPC181225
0.8636	High Similarity	NPC290690
0.8636	High Similarity	NPC52169
0.8636	High Similarity	NPC473242
0.8636	High Similarity	NPC472802
0.8636	High Similarity	NPC470629
0.8636	High Similarity	NPC182797
0.8621	High Similarity	NPC235341
0.8621	High Similarity	NPC72638
0.8621	High Similarity	NPC95594
0.8621	High Similarity	NPC477579
0.8605	High Similarity	NPC171789
0.8588	High Similarity	NPC48362
0.8588	High Similarity	NPC310989
0.8587	High Similarity	NPC98874
0.8571	High Similarity	NPC474882
0.8571	High Similarity	NPC245972
0.8571	High Similarity	NPC196485
0.8571	High Similarity	NPC160413
0.8571	High Similarity	NPC74751
0.8556	High Similarity	NPC187722
0.8556	High Similarity	NPC38754
0.8556	High Similarity	NPC105189
0.8556	High Similarity	NPC235704
0.8539	High Similarity	NPC474686
0.8539	High Similarity	NPC470588
0.8539	High Similarity	NPC130520
0.8539	High Similarity	NPC68148
0.8539	High Similarity	NPC293048
0.8539	High Similarity	NPC127689
0.8539	High Similarity	NPC25906
0.8539	High Similarity	NPC64872
0.8539	High Similarity	NPC65615
0.8539	High Similarity	NPC270768
0.8539	High Similarity	NPC59263
0.8539	High Similarity	NPC61543
0.8539	High Similarity	NPC234346
0.8539	High Similarity	NPC225585
0.8539	High Similarity	NPC290972
0.8539	High Similarity	NPC69627
0.8539	High Similarity	NPC121798
0.8539	High Similarity	NPC263393
0.8523	High Similarity	NPC68160
0.8523	High Similarity	NPC142415
0.8523	High Similarity	NPC18064
0.8523	High Similarity	NPC51700
0.8523	High Similarity	NPC130577
0.8523	High Similarity	NPC98442
0.8523	High Similarity	NPC242468
0.8523	High Similarity	NPC171203
0.8523	High Similarity	NPC293564
0.8523	High Similarity	NPC307426
0.8523	High Similarity	NPC88716
0.8523	High Similarity	NPC102683
0.8471	Intermediate Similarity	NPC3915
0.8462	Intermediate Similarity	NPC118519
0.8462	Intermediate Similarity	NPC202728
0.8462	Intermediate Similarity	NPC158059
0.8462	Intermediate Similarity	NPC12722
0.8462	Intermediate Similarity	NPC229281
0.8444	Intermediate Similarity	NPC474728
0.8444	Intermediate Similarity	NPC120968
0.8444	Intermediate Similarity	NPC290614
0.8444	Intermediate Similarity	NPC252737
0.8444	Intermediate Similarity	NPC18872
0.8444	Intermediate Similarity	NPC85173
0.8444	Intermediate Similarity	NPC49320
0.8444	Intermediate Similarity	NPC477872
0.8444	Intermediate Similarity	NPC130278
0.8444	Intermediate Similarity	NPC210037
0.8444	Intermediate Similarity	NPC7260
0.8444	Intermediate Similarity	NPC193750
0.8444	Intermediate Similarity	NPC273621
0.8444	Intermediate Similarity	NPC227467
0.8427	Intermediate Similarity	NPC246708
0.8427	Intermediate Similarity	NPC40552
0.8421	Intermediate Similarity	NPC118964
0.8409	Intermediate Similarity	NPC94666
0.8404	Intermediate Similarity	NPC471966
0.8387	Intermediate Similarity	NPC473158
0.8372	Intermediate Similarity	NPC163236
0.837	Intermediate Similarity	NPC114159
0.837	Intermediate Similarity	NPC191412
0.837	Intermediate Similarity	NPC159365
0.837	Intermediate Similarity	NPC6818
0.837	Intermediate Similarity	NPC474529
0.837	Intermediate Similarity	NPC209868
0.8353	Intermediate Similarity	NPC2482
0.8352	Intermediate Similarity	NPC60755
0.8352	Intermediate Similarity	NPC185936
0.8352	Intermediate Similarity	NPC248913
0.8352	Intermediate Similarity	NPC71074
0.8352	Intermediate Similarity	NPC228784
0.8352	Intermediate Similarity	NPC285184
0.8352	Intermediate Similarity	NPC300351
0.8352	Intermediate Similarity	NPC472149
0.8352	Intermediate Similarity	NPC77099
0.8352	Intermediate Similarity	NPC272746
0.8352	Intermediate Similarity	NPC84319
0.8352	Intermediate Similarity	NPC235884
0.8352	Intermediate Similarity	NPC155120
0.8352	Intermediate Similarity	NPC282616
0.8352	Intermediate Similarity	NPC324341
0.8352	Intermediate Similarity	NPC25299
0.8352	Intermediate Similarity	NPC966
0.8352	Intermediate Similarity	NPC52021
0.8352	Intermediate Similarity	NPC6255
0.8352	Intermediate Similarity	NPC470590
0.8352	Intermediate Similarity	NPC168027
0.8352	Intermediate Similarity	NPC471588
0.8352	Intermediate Similarity	NPC475708
0.8352	Intermediate Similarity	NPC288833
0.8352	Intermediate Similarity	NPC306541
0.8352	Intermediate Similarity	NPC99380
0.8351	Intermediate Similarity	NPC213366
0.8333	Intermediate Similarity	NPC77263
0.8333	Intermediate Similarity	NPC474245
0.8333	Intermediate Similarity	NPC30522
0.8333	Intermediate Similarity	NPC250592
0.8333	Intermediate Similarity	NPC476808
0.8333	Intermediate Similarity	NPC161751
0.8333	Intermediate Similarity	NPC31985
0.8333	Intermediate Similarity	NPC474972
0.8333	Intermediate Similarity	NPC95246
0.8333	Intermediate Similarity	NPC1015
0.8315	Intermediate Similarity	NPC469314
0.8315	Intermediate Similarity	NPC220930
0.8315	Intermediate Similarity	NPC469317
0.8315	Intermediate Similarity	NPC475740
0.8315	Intermediate Similarity	NPC71507
0.8315	Intermediate Similarity	NPC241875
0.8315	Intermediate Similarity	NPC272039
0.8298	Intermediate Similarity	NPC26413
0.8295	Intermediate Similarity	NPC469993
0.8295	Intermediate Similarity	NPC470574
0.8295	Intermediate Similarity	NPC274724
0.828	Intermediate Similarity	NPC96916
0.828	Intermediate Similarity	NPC473240
0.8276	Intermediate Similarity	NPC53733
0.8261	Intermediate Similarity	NPC118490
0.8261	Intermediate Similarity	NPC74855
0.8261	Intermediate Similarity	NPC477435
0.8261	Intermediate Similarity	NPC477436
0.8261	Intermediate Similarity	NPC275809
0.8261	Intermediate Similarity	NPC133579
0.8261	Intermediate Similarity	NPC307335
0.8261	Intermediate Similarity	NPC298554
0.8261	Intermediate Similarity	NPC136313
0.8261	Intermediate Similarity	NPC474806
0.8261	Intermediate Similarity	NPC86368
0.8242	Intermediate Similarity	NPC113989
0.8242	Intermediate Similarity	NPC86372
0.8242	Intermediate Similarity	NPC172361
0.8242	Intermediate Similarity	NPC120840
0.8222	Intermediate Similarity	NPC1753
0.8222	Intermediate Similarity	NPC474511
0.8222	Intermediate Similarity	NPC471722
0.8222	Intermediate Similarity	NPC474677
0.8222	Intermediate Similarity	NPC474925
0.8202	Intermediate Similarity	NPC474732

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 NPC230387 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	2074
0.2-0.3	4023
0.3-0.4	1974
0.4-0.5	484
0.5-0.6	151
0.6-0.7	170
0.7-0.8	55
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8977	High Similarity	NPD7515	Phase 2
0.8571	High Similarity	NPD7748	Approved
0.8298	Intermediate Similarity	NPD7902	Approved
0.8202	Intermediate Similarity	NPD3618	Phase 1
0.8132	Intermediate Similarity	NPD5328	Approved
0.8132	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5222	Approved
0.8	Intermediate Similarity	NPD5221	Approved
0.8	Intermediate Similarity	NPD4697	Phase 3
0.8	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD7900	Approved
0.7979	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD4786	Approved
0.7957	Intermediate Similarity	NPD6079	Approved
0.7955	Intermediate Similarity	NPD3667	Approved
0.7931	Intermediate Similarity	NPD4695	Discontinued
0.7917	Intermediate Similarity	NPD4755	Approved
0.7917	Intermediate Similarity	NPD5173	Approved
0.7907	Intermediate Similarity	NPD3617	Approved
0.7816	Intermediate Similarity	NPD7645	Phase 2
0.7778	Intermediate Similarity	NPD3665	Phase 1
0.7778	Intermediate Similarity	NPD3666	Approved
0.7778	Intermediate Similarity	NPD3133	Approved
0.7755	Intermediate Similarity	NPD5286	Approved
0.7755	Intermediate Similarity	NPD4700	Approved
0.7755	Intermediate Similarity	NPD4696	Approved
0.7755	Intermediate Similarity	NPD5285	Approved
0.7742	Intermediate Similarity	NPD4753	Phase 2
0.7692	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD4202	Approved
0.7677	Intermediate Similarity	NPD5223	Approved
0.7609	Intermediate Similarity	NPD5279	Phase 3
0.76	Intermediate Similarity	NPD5225	Approved
0.76	Intermediate Similarity	NPD5211	Phase 2
0.76	Intermediate Similarity	NPD4633	Approved
0.76	Intermediate Similarity	NPD5226	Approved
0.76	Intermediate Similarity	NPD5224	Approved
0.7549	Intermediate Similarity	NPD5739	Approved
0.7549	Intermediate Similarity	NPD6675	Approved
0.7549	Intermediate Similarity	NPD6402	Approved
0.7549	Intermediate Similarity	NPD7128	Approved
0.7525	Intermediate Similarity	NPD5175	Approved
0.7525	Intermediate Similarity	NPD4754	Approved
0.7525	Intermediate Similarity	NPD5174	Approved
0.75	Intermediate Similarity	NPD5329	Approved
0.7451	Intermediate Similarity	NPD5141	Approved
0.7419	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD6899	Approved
0.7404	Intermediate Similarity	NPD7320	Approved
0.7404	Intermediate Similarity	NPD6881	Approved
0.7391	Intermediate Similarity	NPD4197	Approved
0.7391	Intermediate Similarity	NPD3668	Phase 3
0.7379	Intermediate Similarity	NPD4768	Approved
0.7379	Intermediate Similarity	NPD4767	Approved
0.7374	Intermediate Similarity	NPD6084	Phase 2
0.7374	Intermediate Similarity	NPD6083	Phase 2
0.7347	Intermediate Similarity	NPD4629	Approved
0.7347	Intermediate Similarity	NPD5210	Approved
0.7333	Intermediate Similarity	NPD6373	Approved
0.7333	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6372	Approved
0.732	Intermediate Similarity	NPD6399	Phase 3
0.7308	Intermediate Similarity	NPD5701	Approved
0.7308	Intermediate Similarity	NPD5697	Approved
0.7264	Intermediate Similarity	NPD6883	Approved
0.7264	Intermediate Similarity	NPD7290	Approved
0.7264	Intermediate Similarity	NPD7102	Approved
0.7263	Intermediate Similarity	NPD5737	Approved
0.7263	Intermediate Similarity	NPD6672	Approved
0.7263	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD4729	Approved
0.7238	Intermediate Similarity	NPD6011	Approved
0.7238	Intermediate Similarity	NPD5128	Approved
0.7238	Intermediate Similarity	NPD5168	Approved
0.7238	Intermediate Similarity	NPD4730	Approved
0.7216	Intermediate Similarity	NPD8034	Phase 2
0.7216	Intermediate Similarity	NPD8035	Phase 2
0.7209	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6869	Approved
0.7196	Intermediate Similarity	NPD6649	Approved
0.7196	Intermediate Similarity	NPD8130	Phase 1
0.7196	Intermediate Similarity	NPD6617	Approved
0.7196	Intermediate Similarity	NPD6847	Approved
0.7196	Intermediate Similarity	NPD6650	Approved
0.7182	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4221	Approved
0.7174	Intermediate Similarity	NPD4223	Phase 3
0.717	Intermediate Similarity	NPD6013	Approved
0.717	Intermediate Similarity	NPD6014	Approved
0.717	Intermediate Similarity	NPD6012	Approved
0.7143	Intermediate Similarity	NPD7525	Registered
0.713	Intermediate Similarity	NPD8297	Approved
0.713	Intermediate Similarity	NPD6882	Approved
0.7129	Intermediate Similarity	NPD7638	Approved
0.7105	Intermediate Similarity	NPD8328	Phase 3
0.7103	Intermediate Similarity	NPD5251	Approved
0.7103	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5247	Approved
0.7103	Intermediate Similarity	NPD5135	Approved
0.7103	Intermediate Similarity	NPD4634	Approved
0.7103	Intermediate Similarity	NPD5248	Approved
0.7103	Intermediate Similarity	NPD5249	Phase 3
0.7103	Intermediate Similarity	NPD5250	Approved
0.7103	Intermediate Similarity	NPD5169	Approved
0.71	Intermediate Similarity	NPD7614	Phase 1
0.7097	Intermediate Similarity	NPD4788	Approved
0.7093	Intermediate Similarity	NPD4789	Approved
0.7079	Intermediate Similarity	NPD6117	Approved
0.7059	Intermediate Similarity	NPD7640	Approved
0.7059	Intermediate Similarity	NPD7639	Approved
0.7053	Intermediate Similarity	NPD5690	Phase 2
0.7053	Intermediate Similarity	NPD5280	Approved
0.7053	Intermediate Similarity	NPD4694	Approved
0.7053	Intermediate Similarity	NPD7521	Approved
0.7053	Intermediate Similarity	NPD6684	Approved
0.7053	Intermediate Similarity	NPD6409	Approved
0.7053	Intermediate Similarity	NPD7146	Approved
0.7053	Intermediate Similarity	NPD7334	Approved
0.7053	Intermediate Similarity	NPD5330	Approved
0.7037	Intermediate Similarity	NPD5127	Approved
0.7037	Intermediate Similarity	NPD5215	Approved
0.7037	Intermediate Similarity	NPD5217	Approved
0.7037	Intermediate Similarity	NPD5216	Approved
0.7009	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6116	Phase 1
0.7	Intermediate Similarity	NPD5695	Phase 3
0.6979	Remote Similarity	NPD3573	Approved
0.6966	Remote Similarity	NPD7339	Approved
0.6966	Remote Similarity	NPD3703	Phase 2
0.6966	Remote Similarity	NPD6942	Approved
0.6961	Remote Similarity	NPD5696	Approved
0.6937	Remote Similarity	NPD6868	Approved
0.6923	Remote Similarity	NPD6697	Approved
0.6923	Remote Similarity	NPD6118	Approved
0.6923	Remote Similarity	NPD7632	Discontinued
0.6923	Remote Similarity	NPD6115	Approved
0.6923	Remote Similarity	NPD6114	Approved
0.6909	Remote Similarity	NPD4632	Approved
0.6907	Remote Similarity	NPD6903	Approved
0.6897	Remote Similarity	NPD4244	Approved
0.6897	Remote Similarity	NPD4245	Approved
0.6889	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4623	Approved
0.6875	Remote Similarity	NPD5205	Approved
0.6875	Remote Similarity	NPD4138	Approved
0.6875	Remote Similarity	NPD4519	Discontinued
0.6875	Remote Similarity	NPD4690	Approved
0.6875	Remote Similarity	NPD7115	Discovery
0.6875	Remote Similarity	NPD4688	Approved
0.6875	Remote Similarity	NPD4693	Phase 3
0.6875	Remote Similarity	NPD4689	Approved
0.6854	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5167	Approved
0.6837	Remote Similarity	NPD6673	Approved
0.6837	Remote Similarity	NPD6080	Approved
0.6837	Remote Similarity	NPD6904	Approved
0.6822	Remote Similarity	NPD6412	Phase 2
0.6814	Remote Similarity	NPD6335	Approved
0.6786	Remote Similarity	NPD6274	Approved
0.6782	Remote Similarity	NPD3698	Phase 2
0.6771	Remote Similarity	NPD1696	Phase 3
0.6765	Remote Similarity	NPD7732	Phase 3
0.6754	Remote Similarity	NPD7100	Approved
0.6754	Remote Similarity	NPD7101	Approved
0.6726	Remote Similarity	NPD6317	Approved
0.6726	Remote Similarity	NPD6009	Approved
0.6706	Remote Similarity	NPD7341	Phase 2
0.6702	Remote Similarity	NPD4139	Approved
0.6702	Remote Similarity	NPD4692	Approved
0.67	Remote Similarity	NPD6411	Approved
0.6697	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6059	Approved
0.6696	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD5360	Phase 3
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6908	Approved
0.6638	Remote Similarity	NPD6909	Approved
0.6634	Remote Similarity	NPD5133	Approved
0.6628	Remote Similarity	NPD3704	Approved
0.6596	Remote Similarity	NPD4748	Discontinued
0.6591	Remote Similarity	NPD4137	Phase 3
0.6583	Remote Similarity	NPD7736	Approved
0.6581	Remote Similarity	NPD6370	Approved
0.6574	Remote Similarity	NPD6008	Approved
0.6559	Remote Similarity	NPD3671	Phase 1
0.6552	Remote Similarity	NPD6319	Approved
0.6535	Remote Similarity	NPD5284	Approved
0.6535	Remote Similarity	NPD5693	Phase 1
0.6535	Remote Similarity	NPD6050	Approved
0.6535	Remote Similarity	NPD5281	Approved
0.6531	Remote Similarity	NPD6098	Approved
0.6526	Remote Similarity	NPD8028	Phase 2
0.6525	Remote Similarity	NPD7604	Phase 2

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