NPASS Compound

Structure

CID171148 OpenBabel06191715542D 42 43 0 0 1 0 0 0 0 0999 V2000 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -6.0000 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 13.8564 -6.0000 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 12.4904 -9.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9904 -8.5000 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 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -4.5000 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 12.1244 -6.0000 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 12.1244 -7.0000 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 14.7224 -7.5000 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 13.8564 -9.0000 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 9.5263 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 -7.0000 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 14.7224 -8.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 12.9904 -7.5000 0.0000 C 0 0 3 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 12.9904 -8.5000 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 15.5885 -9.0000 0.0000 O 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 29 1 0 0 0 0 2 30 1 0 0 0 0 3 31 1 0 0 0 0 4 32 1 0 0 0 0 5 33 1 0 0 0 0 6 34 1 0 0 0 0 7 39 1 0 0 0 0 8 39 1 0 0 0 0 9 40 1 0 0 0 0 10 40 1 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 29 2 0 0 0 0 16 30 2 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 31 2 0 0 0 0 20 32 2 0 0 0 0 21 23 2 0 0 0 0 21 31 1 0 0 0 0 22 24 2 0 0 0 0 22 32 1 0 0 0 0 23 37 1 0 0 0 0 24 38 1 0 0 0 0 25 33 2 0 0 0 0 25 35 1 0 0 0 0 26 34 1 0 0 0 0 26 36 1 0 0 0 0 27 35 1 0 0 0 0 27 39 1 0 0 0 0 28 36 1 0 0 0 0 28 40 1 0 0 0 0 33 37 1 0 0 0 0 34 38 2 0 0 0 0 35 41 1 0 0 0 0 36 42 1 0 0 0 0 37 39 1 0 0 0 0 38 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	568.43
Volume:	671.862
LogP:	5.611
LogD:	4.421
LogS:	-4.419
# Rotatable Bonds:	10
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.203
Synthetic Accessibility Score:	4.96
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:	-5.35
MDCK Permeability:	1.4917401131242514e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	102.64568328857422%
Volume Distribution (VD):	1.004
Pgp-substrate:	3.4870412349700928%

ADMET: Metabolism

CYP1A2-inhibitor:	0.442
CYP1A2-substrate:	0.902
CYP2C19-inhibitor:	0.828
CYP2C19-substrate:	0.943
CYP2C9-inhibitor:	0.695
CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	0.948
CYP2D6-substrate:	0.98
CYP3A4-inhibitor:	0.865
CYP3A4-substrate:	0.512

ADMET: Excretion

Clearance (CL):	1.353
Half-life (T1/2):	0.019

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.059
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.106
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.034
Carcinogencity:	0.048
Eye Corrosion:	0.003
Eye Irritation:	0.093
Respiratory Toxicity:	0.591

Download Data

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

Natural Product: NPC171148

Natural Product ID:	NPC171148
*Common Name:**	4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(4-Hydroxy-2,6,6-Trimethylcyclohex-2-En-1-Yl)-3,7,12,16-Tetramethyloctadeca-1,3,5,7,9,11,13,15,17-Nonaenyl]-3,5,5-Trimethylcyclohex-3-En-1-Ol
IUPAC Name:	4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-3-en-1-ol
Synonyms:
Standard InCHIKey:	KBPHJBAIARWVSC-DKLMTRRASA-N
Standard InCHI:	InChI=1S/C40H56O2/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/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+
SMILES:	C/C(=CC=CC=C(C=CC=C(C=CC1=C(C)CC(CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/C1C(=CC(CC1(C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1979448
PubChem CID:	5368396
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001554] Tetraterpenoids [CHEMONTID:0001277] Carotenoids [CHEMONTID:0001410] Xanthophylls

*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
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10606602]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[12467621]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12932131]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	root	n.a.	PMID[16212233]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	branch	n.a.	PMID[17202693]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17689080]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20460582]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22272932]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	root bark	n.a.	n.a.	PMID[23282106]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23872723]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[25172746]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25320841]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[26982999]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31397570]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32996318]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8910532]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[9090870]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO27653	Lablab niger	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27653	Lablab niger	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16749	Zostera marina	Species	Zosteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16749	Zostera marina	Species	Zosteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27653	Lablab niger	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8650	Perilla frutescens	Species	Lamiaceae	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
NPO42047	NPC171148	n.a.	Seeds	3.68 ± 0.03	n.a.	n.a.	mg/kg of seed oil	PMID[28255501]

☑ 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
GI50	54

Activity Type	# Activity
Cell Line	54

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	18663.8	nM	PMID[476185]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	24660.39	nM	PMID[476185]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	33962.53	nM	PMID[476185]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	16595.87	nM	PMID[476185]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	51641.64	nM	PMID[476185]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	21428.91	nM	PMID[476185]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	7430.19	nM	PMID[476185]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	16634.13	nM	PMID[476185]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	15631.48	nM	PMID[476185]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	38282.47	nM	PMID[476185]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	17298.16	nM	PMID[476185]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	20892.96	nM	PMID[476185]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	24490.63	nM	PMID[476185]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	34833.73	nM	PMID[476185]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	19678.86	nM	PMID[476185]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	53210.83	nM	PMID[476185]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	15667.51	nM	PMID[476185]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	13489.63	nM	PMID[476185]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	19098.53	nM	PMID[476185]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	57809.6	nM	PMID[476185]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	15205.48	nM	PMID[476185]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	38636.7	nM	PMID[476185]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	13772.09	nM	PMID[476185]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[476185]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	28248.8	nM	PMID[476185]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	28773.98	nM	PMID[476185]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	56104.8	nM	PMID[476185]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	17823.79	nM	PMID[476185]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[476185]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	35645.11	nM	PMID[476185]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	83946.0	nM	PMID[476185]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	26546.06	nM	PMID[476185]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	19678.86	nM	PMID[476185]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	15739.83	nM	PMID[476185]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	79250.13	nM	PMID[476185]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	27733.2	nM	PMID[476185]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	23173.95	nM	PMID[476185]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	40831.94	nM	PMID[476185]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	19952.62	nM	PMID[476185]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	32583.67	nM	PMID[476185]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	14962.36	nM	PMID[476185]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	23173.95	nM	PMID[476185]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	17538.81	nM	PMID[476185]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	26546.06	nM	PMID[476185]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	23878.11	nM	PMID[476185]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	80537.84	nM	PMID[476185]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	24888.57	nM	PMID[476185]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	19142.56	nM	PMID[476185]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	26181.83	nM	PMID[476185]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	21428.91	nM	PMID[476185]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	17538.81	nM	PMID[476185]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	14893.61	nM	PMID[476185]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	18492.69	nM	PMID[476185]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	20749.14	nM	PMID[476185]

☑ 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 NPC171148 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	168
0.1-0.2	1171
0.2-0.3	7067
0.3-0.4	17029
0.4-0.5	10021
0.5-0.6	5425
0.6-0.7	1553
0.7-0.8	246
0.8-0.85	10
0.85-0.9	1
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC313179
1.0	High Similarity	NPC69383
0.8986	High Similarity	NPC45782
0.863	High Similarity	NPC130665
0.8608	High Similarity	NPC238485
0.8533	High Similarity	NPC265588
0.8481	Intermediate Similarity	NPC470384
0.8472	Intermediate Similarity	NPC471560
0.8451	Intermediate Similarity	NPC114651
0.8421	Intermediate Similarity	NPC91594
0.8378	Intermediate Similarity	NPC68443
0.8375	Intermediate Similarity	NPC231310
0.8356	Intermediate Similarity	NPC34834
0.8354	Intermediate Similarity	NPC202389
0.8333	Intermediate Similarity	NPC96362
0.8312	Intermediate Similarity	NPC167891
0.8312	Intermediate Similarity	NPC83351
0.8312	Intermediate Similarity	NPC476314
0.8289	Intermediate Similarity	NPC253190
0.8286	Intermediate Similarity	NPC290367
0.8267	Intermediate Similarity	NPC306727
0.8267	Intermediate Similarity	NPC243342
0.8267	Intermediate Similarity	NPC477138
0.8243	Intermediate Similarity	NPC242001
0.8228	Intermediate Similarity	NPC476646
0.8219	Intermediate Similarity	NPC473893
0.8158	Intermediate Similarity	NPC291503
0.8133	Intermediate Similarity	NPC471799
0.8125	Intermediate Similarity	NPC87489
0.8125	Intermediate Similarity	NPC471408
0.8108	Intermediate Similarity	NPC145498
0.8101	Intermediate Similarity	NPC234193
0.8082	Intermediate Similarity	NPC471238
0.8082	Intermediate Similarity	NPC208999
0.8082	Intermediate Similarity	NPC96484
0.8052	Intermediate Similarity	NPC106432
0.8049	Intermediate Similarity	NPC109528
0.8026	Intermediate Similarity	NPC201048
0.8026	Intermediate Similarity	NPC471797
0.8026	Intermediate Similarity	NPC91858
0.8026	Intermediate Similarity	NPC476366
0.8025	Intermediate Similarity	NPC82538
0.8025	Intermediate Similarity	NPC237795
0.8	Intermediate Similarity	NPC264245
0.8	Intermediate Similarity	NPC95863
0.8	Intermediate Similarity	NPC477792
0.8	Intermediate Similarity	NPC249423
0.8	Intermediate Similarity	NPC110799
0.7975	Intermediate Similarity	NPC81306
0.7975	Intermediate Similarity	NPC109546
0.7975	Intermediate Similarity	NPC84694
0.7975	Intermediate Similarity	NPC143182
0.7975	Intermediate Similarity	NPC30986
0.7975	Intermediate Similarity	NPC28862
0.7975	Intermediate Similarity	NPC209430
0.7975	Intermediate Similarity	NPC47982
0.7973	Intermediate Similarity	NPC9942
0.7949	Intermediate Similarity	NPC471798
0.7949	Intermediate Similarity	NPC470711
0.7949	Intermediate Similarity	NPC470758
0.7945	Intermediate Similarity	NPC68703
0.7945	Intermediate Similarity	NPC69649
0.7922	Intermediate Similarity	NPC66566
0.7922	Intermediate Similarity	NPC477923
0.7901	Intermediate Similarity	NPC50964
0.7901	Intermediate Similarity	NPC49964
0.7901	Intermediate Similarity	NPC201852
0.7895	Intermediate Similarity	NPC265485
0.7895	Intermediate Similarity	NPC182717
0.7895	Intermediate Similarity	NPC220939
0.7875	Intermediate Similarity	NPC164840
0.7875	Intermediate Similarity	NPC295131
0.7875	Intermediate Similarity	NPC241290
0.7875	Intermediate Similarity	NPC209944
0.7867	Intermediate Similarity	NPC92801
0.7867	Intermediate Similarity	NPC189745
0.7867	Intermediate Similarity	NPC49422
0.7867	Intermediate Similarity	NPC9161
0.7848	Intermediate Similarity	NPC11908
0.7848	Intermediate Similarity	NPC307965
0.7848	Intermediate Similarity	NPC18603
0.7848	Intermediate Similarity	NPC318136
0.7848	Intermediate Similarity	NPC186191
0.7848	Intermediate Similarity	NPC72507
0.7848	Intermediate Similarity	NPC205455
0.7848	Intermediate Similarity	NPC76931
0.7848	Intermediate Similarity	NPC275910
0.7848	Intermediate Similarity	NPC474216
0.7838	Intermediate Similarity	NPC216460
0.7821	Intermediate Similarity	NPC477925
0.7821	Intermediate Similarity	NPC274079
0.7821	Intermediate Similarity	NPC470749
0.7821	Intermediate Similarity	NPC470362
0.7816	Intermediate Similarity	NPC310013
0.7808	Intermediate Similarity	NPC202017
0.7808	Intermediate Similarity	NPC149680
0.7805	Intermediate Similarity	NPC317458
0.7805	Intermediate Similarity	NPC57370
0.7792	Intermediate Similarity	NPC469534
0.7792	Intermediate Similarity	NPC469593
0.7792	Intermediate Similarity	NPC469533
0.7778	Intermediate Similarity	NPC23852
0.7778	Intermediate Similarity	NPC47761
0.7778	Intermediate Similarity	NPC6663
0.7778	Intermediate Similarity	NPC209620
0.7778	Intermediate Similarity	NPC159148
0.7763	Intermediate Similarity	NPC167706
0.7763	Intermediate Similarity	NPC471268
0.7763	Intermediate Similarity	NPC471272
0.7763	Intermediate Similarity	NPC471271
0.7763	Intermediate Similarity	NPC23954
0.7738	Intermediate Similarity	NPC281316
0.7738	Intermediate Similarity	NPC261266
0.7733	Intermediate Similarity	NPC167272
0.7733	Intermediate Similarity	NPC474248
0.7733	Intermediate Similarity	NPC269877
0.7722	Intermediate Similarity	NPC214570
0.7722	Intermediate Similarity	NPC477924
0.7714	Intermediate Similarity	NPC122239
0.7711	Intermediate Similarity	NPC205845
0.7711	Intermediate Similarity	NPC302360
0.7692	Intermediate Similarity	NPC471468
0.7692	Intermediate Similarity	NPC32832
0.7683	Intermediate Similarity	NPC189972
0.7683	Intermediate Similarity	NPC296701
0.7683	Intermediate Similarity	NPC101462
0.7683	Intermediate Similarity	NPC218616
0.7671	Intermediate Similarity	NPC163678
0.7671	Intermediate Similarity	NPC308844
0.7654	Intermediate Similarity	NPC287749
0.7654	Intermediate Similarity	NPC281880
0.7654	Intermediate Similarity	NPC74086
0.7647	Intermediate Similarity	NPC245004
0.7639	Intermediate Similarity	NPC83200
0.7625	Intermediate Similarity	NPC473943
0.7625	Intermediate Similarity	NPC470396
0.7625	Intermediate Similarity	NPC474989
0.7625	Intermediate Similarity	NPC99168
0.7625	Intermediate Similarity	NPC22955
0.7619	Intermediate Similarity	NPC274448
0.7619	Intermediate Similarity	NPC157257
0.76	Intermediate Similarity	NPC117804
0.76	Intermediate Similarity	NPC32055
0.7595	Intermediate Similarity	NPC129165
0.7595	Intermediate Similarity	NPC134330
0.7595	Intermediate Similarity	NPC113733
0.7595	Intermediate Similarity	NPC202642
0.7595	Intermediate Similarity	NPC321016
0.7595	Intermediate Similarity	NPC321381
0.7595	Intermediate Similarity	NPC107059
0.7595	Intermediate Similarity	NPC73875
0.7595	Intermediate Similarity	NPC46160
0.7595	Intermediate Similarity	NPC247325
0.7595	Intermediate Similarity	NPC244488
0.759	Intermediate Similarity	NPC474634
0.759	Intermediate Similarity	NPC475789
0.7586	Intermediate Similarity	NPC19771
0.7568	Intermediate Similarity	NPC326310
0.7568	Intermediate Similarity	NPC250977
0.7568	Intermediate Similarity	NPC286669
0.7568	Intermediate Similarity	NPC279434
0.7568	Intermediate Similarity	NPC222366
0.7568	Intermediate Similarity	NPC476406
0.7568	Intermediate Similarity	NPC267027
0.7568	Intermediate Similarity	NPC476039
0.7564	Intermediate Similarity	NPC329090
0.7564	Intermediate Similarity	NPC100334
0.7564	Intermediate Similarity	NPC27395
0.7561	Intermediate Similarity	NPC474759
0.7561	Intermediate Similarity	NPC142163
0.7561	Intermediate Similarity	NPC82986
0.7561	Intermediate Similarity	NPC474752
0.7561	Intermediate Similarity	NPC474683
0.7561	Intermediate Similarity	NPC7505
0.7561	Intermediate Similarity	NPC474731
0.7561	Intermediate Similarity	NPC6707
0.7558	Intermediate Similarity	NPC280556
0.7558	Intermediate Similarity	NPC229612
0.7558	Intermediate Similarity	NPC7280
0.7536	Intermediate Similarity	NPC55412
0.7536	Intermediate Similarity	NPC48891
0.7536	Intermediate Similarity	NPC249645
0.7534	Intermediate Similarity	NPC225415
0.7534	Intermediate Similarity	NPC323424
0.7534	Intermediate Similarity	NPC96793
0.7532	Intermediate Similarity	NPC164022
0.7531	Intermediate Similarity	NPC53744
0.7531	Intermediate Similarity	NPC291379
0.7531	Intermediate Similarity	NPC19900
0.7531	Intermediate Similarity	NPC100906
0.7529	Intermediate Similarity	NPC6391
0.7528	Intermediate Similarity	NPC78159
0.75	Intermediate Similarity	NPC101475
0.75	Intermediate Similarity	NPC157996
0.75	Intermediate Similarity	NPC198968
0.75	Intermediate Similarity	NPC475251
0.75	Intermediate Similarity	NPC474047
0.75	Intermediate Similarity	NPC34177
0.75	Intermediate Similarity	NPC469728
0.75	Intermediate Similarity	NPC203403

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 NPC171148 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1637
0.2-0.3	4098
0.3-0.4	2310
0.4-0.5	706
0.5-0.6	165
0.6-0.7	53
0.7-0.8	23
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8264	Approved
0.8077	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7150	Approved
0.8	Intermediate Similarity	NPD7152	Approved
0.8	Intermediate Similarity	NPD7151	Approved
0.7875	Intermediate Similarity	NPD7514	Phase 3
0.7875	Intermediate Similarity	NPD7332	Phase 2
0.7867	Intermediate Similarity	NPD7143	Approved
0.7867	Intermediate Similarity	NPD7144	Approved
0.7848	Intermediate Similarity	NPD7145	Approved
0.7778	Intermediate Similarity	NPD6902	Approved
0.7733	Intermediate Similarity	NPD6923	Approved
0.7733	Intermediate Similarity	NPD6922	Approved
0.7722	Intermediate Similarity	NPD5776	Phase 2
0.7722	Intermediate Similarity	NPD6925	Approved
0.7654	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6926	Approved
0.7564	Intermediate Similarity	NPD6924	Approved
0.7536	Intermediate Similarity	NPD4219	Approved
0.7531	Intermediate Similarity	NPD6929	Approved
0.75	Intermediate Similarity	NPD6932	Approved
0.7468	Intermediate Similarity	NPD6942	Approved
0.7468	Intermediate Similarity	NPD7339	Approved
0.7439	Intermediate Similarity	NPD6930	Phase 2
0.7439	Intermediate Similarity	NPD6931	Approved
0.7375	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6933	Approved
0.7349	Intermediate Similarity	NPD6898	Phase 1
0.7317	Intermediate Similarity	NPD7645	Phase 2
0.726	Intermediate Similarity	NPD368	Approved
0.7229	Intermediate Similarity	NPD7509	Discontinued
0.7176	Intermediate Similarity	NPD6695	Phase 3
0.7108	Intermediate Similarity	NPD6683	Phase 2
0.7093	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7750	Discontinued
0.7033	Intermediate Similarity	NPD5778	Approved
0.7033	Intermediate Similarity	NPD5779	Approved
0.7024	Intermediate Similarity	NPD7525	Registered
0.7011	Intermediate Similarity	NPD6893	Approved
0.7	Intermediate Similarity	NPD4732	Discontinued
0.6923	Remote Similarity	NPD7637	Suspended
0.6923	Remote Similarity	NPD6411	Approved
0.6897	Remote Similarity	NPD4786	Approved
0.686	Remote Similarity	NPD3667	Approved
0.6854	Remote Similarity	NPD7524	Approved
0.6824	Remote Similarity	NPD4748	Discontinued
0.6818	Remote Similarity	NPD1696	Phase 3
0.6813	Remote Similarity	NPD7136	Phase 2
0.6742	Remote Similarity	NPD5279	Phase 3
0.6707	Remote Similarity	NPD4784	Approved
0.6707	Remote Similarity	NPD4785	Approved
0.6703	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD342	Phase 1
0.6588	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4194	Approved
0.6579	Remote Similarity	NPD4193	Approved
0.6579	Remote Similarity	NPD4191	Approved
0.6579	Remote Similarity	NPD4192	Approved
0.6559	Remote Similarity	NPD6079	Approved
0.6559	Remote Similarity	NPD7087	Discontinued
0.6556	Remote Similarity	NPD3618	Phase 1
0.6522	Remote Similarity	NPD5328	Approved
0.6522	Remote Similarity	NPD8262	Approved
0.6517	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD4243	Approved
0.6429	Remote Similarity	NPD8039	Approved
0.641	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7515	Phase 2
0.6333	Remote Similarity	NPD3665	Phase 1
0.6333	Remote Similarity	NPD3666	Approved
0.6333	Remote Similarity	NPD3133	Approved
0.6327	Remote Similarity	NPD4225	Approved
0.6263	Remote Similarity	NPD7639	Approved
0.6263	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD4822	Approved
0.625	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD7748	Approved
0.625	Remote Similarity	NPD4821	Approved
0.625	Remote Similarity	NPD4819	Approved
0.6234	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5362	Discontinued
0.6222	Remote Similarity	NPD5332	Approved
0.6222	Remote Similarity	NPD5331	Approved
0.6207	Remote Similarity	NPD4268	Approved
0.6207	Remote Similarity	NPD4271	Approved
0.6196	Remote Similarity	NPD4623	Approved
0.6196	Remote Similarity	NPD4519	Discontinued
0.618	Remote Similarity	NPD4790	Discontinued
0.6162	Remote Similarity	NPD7638	Approved
0.6154	Remote Similarity	NPD3668	Phase 3
0.6146	Remote Similarity	NPD4202	Approved
0.6146	Remote Similarity	NPD6399	Phase 3
0.6139	Remote Similarity	NPD5211	Phase 2
0.6136	Remote Similarity	NPD4195	Approved
0.6122	Remote Similarity	NPD5221	Approved
0.6122	Remote Similarity	NPD5222	Approved
0.6122	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4269	Approved
0.6111	Remote Similarity	NPD4270	Approved
0.6087	Remote Similarity	NPD4265	Approved
0.6067	Remote Similarity	NPD4252	Approved
0.6067	Remote Similarity	NPD4695	Discontinued
0.6067	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4518	Approved
0.6061	Remote Similarity	NPD7902	Approved
0.6061	Remote Similarity	NPD5173	Approved
0.6047	Remote Similarity	NPD5275	Approved
0.6047	Remote Similarity	NPD4190	Phase 3
0.6044	Remote Similarity	NPD7154	Phase 3
0.6042	Remote Similarity	NPD7983	Approved
0.6022	Remote Similarity	NPD4694	Approved
0.6022	Remote Similarity	NPD5280	Approved
0.6019	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD5290	Discontinued
0.6	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6640	Phase 3
0.596	Remote Similarity	NPD7839	Suspended
0.596	Remote Similarity	NPD4697	Phase 3
0.5941	Remote Similarity	NPD6648	Approved
0.5941	Remote Similarity	NPD5285	Approved
0.5941	Remote Similarity	NPD5286	Approved
0.5941	Remote Similarity	NPD4696	Approved
0.5938	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7838	Discovery
0.5938	Remote Similarity	NPD5785	Approved
0.593	Remote Similarity	NPD4687	Approved
0.593	Remote Similarity	NPD5733	Approved
0.5914	Remote Similarity	NPD5363	Approved
0.5914	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4755	Approved
0.5882	Remote Similarity	NPD5276	Approved
0.5882	Remote Similarity	NPD5344	Discontinued
0.5882	Remote Similarity	NPD5223	Approved
0.5876	Remote Similarity	NPD5281	Approved
0.5876	Remote Similarity	NPD5284	Approved
0.5856	Remote Similarity	NPD7115	Discovery
0.5851	Remote Similarity	NPD5786	Approved
0.5851	Remote Similarity	NPD5690	Phase 2
0.5833	Remote Similarity	NPD4753	Phase 2
0.5833	Remote Similarity	NPD6051	Approved
0.5825	Remote Similarity	NPD5226	Approved
0.5825	Remote Similarity	NPD4633	Approved
0.5825	Remote Similarity	NPD5224	Approved
0.5825	Remote Similarity	NPD5225	Approved
0.581	Remote Similarity	NPD7333	Discontinued
0.5784	Remote Similarity	NPD4700	Approved
0.5784	Remote Similarity	NPD6404	Discontinued
0.5783	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD4096	Approved
0.5769	Remote Similarity	NPD5174	Approved
0.5769	Remote Similarity	NPD5175	Approved
0.5769	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD4221	Approved
0.5761	Remote Similarity	NPD4223	Phase 3
0.5758	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD7900	Approved
0.5747	Remote Similarity	NPD4058	Approved
0.5745	Remote Similarity	NPD5329	Approved
0.5728	Remote Similarity	NPD4159	Approved
0.5702	Remote Similarity	NPD7741	Discontinued
0.5702	Remote Similarity	NPD3091	Approved
0.5701	Remote Similarity	NPD6881	Approved
0.5701	Remote Similarity	NPD6899	Approved
0.57	Remote Similarity	NPD5210	Approved
0.57	Remote Similarity	NPD4629	Approved
0.5699	Remote Similarity	NPD6110	Phase 1
0.5688	Remote Similarity	NPD8130	Phase 1
0.5684	Remote Similarity	NPD5330	Approved
0.5684	Remote Similarity	NPD6684	Approved
0.5684	Remote Similarity	NPD7146	Approved
0.5684	Remote Similarity	NPD6409	Approved
0.5684	Remote Similarity	NPD7521	Approved
0.5684	Remote Similarity	NPD7334	Approved
0.5673	Remote Similarity	NPD7632	Discontinued
0.5663	Remote Similarity	NPD7331	Phase 2
0.566	Remote Similarity	NPD7128	Approved
0.566	Remote Similarity	NPD6402	Approved
0.566	Remote Similarity	NPD5739	Approved
0.566	Remote Similarity	NPD6675	Approved
0.5652	Remote Similarity	NPD5369	Approved
0.5647	Remote Similarity	NPD15	Approved
0.5647	Remote Similarity	NPD791	Approved
0.5638	Remote Similarity	NPD4197	Approved
0.5636	Remote Similarity	NPD8297	Approved
0.5625	Remote Similarity	NPD4251	Approved
0.5625	Remote Similarity	NPD4250	Approved
0.5619	Remote Similarity	NPD4754	Approved
0.5618	Remote Similarity	NPD1346	Approved
0.5607	Remote Similarity	NPD5697	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