NPASS Compound

Structure

CID78159 OpenBabel06191715412D 44 45 0 0 1 0 0 0 0 0999 V2000 8.6897 0.3029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1081 0.1175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0859 -2.0934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8348 -0.7596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.1739 -3.7979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5574 -0.5246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.6125 -0.7778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3363 1.3363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1311 2.1835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1833 2.1927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4916 1.5010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5796 -0.2035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2183 0.6239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1282 1.9395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5466 1.7542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3264 0.7414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5245 -0.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9100 1.3156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2733 0.8771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7226 -1.6548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6675 -1.9080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.8106 -3.3593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.2491 -1.7227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9449 -0.2532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3814 0.9946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8549 1.0624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7777 -1.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5816 0.1853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.8656 -3.1062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.5023 -2.6676 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6944 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.6125 -2.1612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6367 0.4385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.3042 -1.4695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 17.4472 -2.9208 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3835 1.3835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1277 0.9699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 29 1 0 0 0 0 3 30 1 0 0 0 0 4 31 1 0 0 0 0 5 32 1 0 0 0 0 6 33 1 0 0 0 0 7 38 1 0 0 0 0 8 38 1 0 0 0 0 9 39 1 0 0 0 0 10 39 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 18 1 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 15 28 2 0 0 0 0 16 29 2 0 0 0 0 17 28 1 0 0 0 0 18 30 2 0 0 0 0 19 29 1 0 0 0 0 20 31 2 0 0 0 0 21 22 3 0 0 0 0 21 30 1 0 0 0 0 22 36 1 0 0 0 0 23 32 1 0 0 0 0 23 34 1 0 0 0 0 24 33 2 0 0 0 0 24 35 1 0 0 0 0 25 34 1 0 0 0 0 25 38 1 0 0 0 0 26 35 1 0 0 0 0 26 39 1 0 0 0 0 27 37 1 0 0 0 0 27 40 1 0 0 0 0 31 37 1 0 0 0 0 32 36 2 0 0 0 0 33 40 1 0 0 0 0 34 41 1 6 0 0 0 35 42 2 0 0 0 0 36 38 1 0 0 0 0 37 43 2 0 0 0 0 39 40 1 0 0 0 0 40 44 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	596.39
Volume:	684.17
LogP:	5.077
LogD:	4.142
LogS:	-5.408
# Rotatable Bonds:	9
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.159
Synthetic Accessibility Score:	5.052
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:	-5.214
MDCK Permeability:	1.4699872735945974e-05
Pgp-inhibitor:	0.046
Pgp-substrate:	0.803
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	100.19552612304688%
Volume Distribution (VD):	1.913
Pgp-substrate:	3.2592759132385254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.248
CYP1A2-substrate:	0.842
CYP2C19-inhibitor:	0.917
CYP2C19-substrate:	0.928
CYP2C9-inhibitor:	0.934
CYP2C9-substrate:	0.996
CYP2D6-inhibitor:	0.924
CYP2D6-substrate:	0.935
CYP3A4-inhibitor:	0.977
CYP3A4-substrate:	0.823

ADMET: Excretion

Clearance (CL):	3.634
Half-life (T1/2):	0.012

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.464
Drug-inuced Liver Injury (DILI):	0.116
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.907
Carcinogencity:	0.892
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC78159

Natural Product ID:	NPC78159
*Common Name:**	Amarouciaxanthin B
IUPAC Name:	(4S)-4-hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7,12,16-tetramethyl-2-oxooctadeca-3,5,7,9,11,13,15-heptaen-17-ynyl]-3,5,5-trimethylcyclohex-2-en-1-one
Synonyms:	amarouciaxanthin B
Standard InCHIKey:	XUKJTNSSWNXSQU-OMEVNMJGSA-N
Standard InCHI:	InChI=1S/C40H52O4/c1-28(17-13-18-30(3)21-22-36-32(5)23-34(41)25-38(36,7)8)15-11-12-16-29(2)19-14-20-31(4)37(43)27-40(44)33(6)24-35(42)26-39(40,9)10/h11-20,24,34,41,44H,23,25-27H2,1-10H3/b12-11+,17-13+,19-14+,28-15+,29-16+,30-18+,31-20+/t34-,40-/m1/s1
SMILES:	C/C(=CC=CC=C(/C)C=CC=C(/C)C(=O)C[C@]1(C(=CC(=O)CC1(C)C)C)O)/C=C/C=C(C)/C#CC1=C(C)C[C@H](CC1(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445440
PubChem CID:	16061221
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
NPO21005	Baphia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(92)80059-N]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	DOI[10.1016/S0040-4039(00)86970-1]
NPO4343	Guanomyces polythrix	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[10869195]
NPO17256	Kobresia nepalensis	Species	Cyperaceae	Eukaryota	n.a.	stem	n.a.	PMID[16508191]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17340534]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	stem	n.a.	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	skin-removed stems	Pingle Town, Sichuang Province, China	2008-AUG	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22690646]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[23397723]
NPO20739	Jungermannia hyalina	Species	Jungermanniaceae	Eukaryota	n.a.	Guangxi Zhuang Autonomous Region, China	n.a.	PMID[25856683]
NPO21618	Ircinia oros	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28840725]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31182315]
NPO20212	Callistemon viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31276403]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[3760884]
NPO5906	Amaroucium pliciferum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[3840198]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6736970]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6875576]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6875577]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	PMID[6875577]
NPO20671	Selliguea feei	Species	Polypodiaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[8254348]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8650.1	Perilla frutescens var. arguta	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19488	Trifolium subterraneum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19488	Trifolium subterraneum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17256	Kobresia nepalensis	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11966	Euphorbia kamerunica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8678	Trillium camschatcense	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8650.1	Perilla frutescens var. arguta	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14466	Penicillium olsonii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20546	Cissus pallidiflorus	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17256	Kobresia nepalensis	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21426	Alstroemeria revoluta	Species	Alstroemeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21486	Marrubium alysson	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21289	Teucrium oxylepis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21231	Astragalus tragacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5906	Amaroucium pliciferum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18096	Excoecaria oppositifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19622	Euphorbia marginata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26840	Litsea aciculata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20671	Selliguea feei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21088	Litsea pulchella	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2854	Gymnosporia senegalensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21365	Ligularia muliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8650.1	Perilla frutescens var. arguta	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20813	Myrmica sabuleti	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17515	Pronephrium triphyllum	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3777	Stevia chamaedrys	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20051	Gardenia collinsae	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19986	Crataegus davisii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11622.1	Shuteria involucrata var. vestita	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3237	Mytilus edulis	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21618	Ircinia oros	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16907	Pentzia incana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15216	Encephalartos altensteinii	Species	Zamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4343	Guanomyces polythrix	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20212	Callistemon viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14136	Acherontia atropus	Species	Sphingidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14330	Agave aurea	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16454	Crinum erubescens	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18620	Grindelia acutifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20612	Ursinia abrotanifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16044	Cupressus lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19488	Trifolium subterraneum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20739	Jungermannia hyalina	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11966	Euphorbia kamerunica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20408	Ajuga spectabilis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13260	Eria foetida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20872	Melampodium heterophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19773	Xenorhabdus bovienii	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21005	Baphia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22510	Eupatorium havanense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21550	Achillea macrophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8678	Trillium camschatcense	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20340	Pausinystalia mayumbensis	Species	Rubiaceae	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	300.0	ug ml-1	PMID[472657]
NPT137	Cell Line	L1210	Mus musculus	ED50	=	100.0	ug ml-1	PMID[472657]

☑ 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 NPC78159 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	194
0.1-0.2	1106
0.2-0.3	5613
0.3-0.4	13611
0.4-0.5	13035
0.5-0.6	6862
0.6-0.7	2087
0.7-0.8	181
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8218	Intermediate Similarity	NPC128828
0.8191	Intermediate Similarity	NPC19771
0.809	Intermediate Similarity	NPC74086
0.7978	Intermediate Similarity	NPC19900
0.7957	Intermediate Similarity	NPC472974
0.7938	Intermediate Similarity	NPC299100
0.7857	Intermediate Similarity	NPC180950
0.7849	Intermediate Similarity	NPC15807
0.7822	Intermediate Similarity	NPC282524
0.7822	Intermediate Similarity	NPC115862
0.7766	Intermediate Similarity	NPC183736
0.7755	Intermediate Similarity	NPC472977
0.7755	Intermediate Similarity	NPC472976
0.7755	Intermediate Similarity	NPC474690
0.7732	Intermediate Similarity	NPC73457
0.7732	Intermediate Similarity	NPC472978
0.7717	Intermediate Similarity	NPC158411
0.7717	Intermediate Similarity	NPC38796
0.7708	Intermediate Similarity	NPC472983
0.7708	Intermediate Similarity	NPC472973
0.7701	Intermediate Similarity	NPC153660
0.7701	Intermediate Similarity	NPC323437
0.7701	Intermediate Similarity	NPC29542
0.7701	Intermediate Similarity	NPC201562
0.77	Intermediate Similarity	NPC161147
0.77	Intermediate Similarity	NPC474938
0.77	Intermediate Similarity	NPC474785
0.767	Intermediate Similarity	NPC475050
0.767	Intermediate Similarity	NPC72151
0.7667	Intermediate Similarity	NPC475994
0.7653	Intermediate Similarity	NPC134826
0.7647	Intermediate Similarity	NPC470184
0.7624	Intermediate Similarity	NPC478056
0.7624	Intermediate Similarity	NPC103051
0.7619	Intermediate Similarity	NPC473284
0.7604	Intermediate Similarity	NPC471791
0.7604	Intermediate Similarity	NPC471793
0.76	Intermediate Similarity	NPC117133
0.76	Intermediate Similarity	NPC250757
0.76	Intermediate Similarity	NPC301534
0.76	Intermediate Similarity	NPC249954
0.7596	Intermediate Similarity	NPC118911
0.7579	Intermediate Similarity	NPC194417
0.7573	Intermediate Similarity	NPC320447
0.7556	Intermediate Similarity	NPC82666
0.7551	Intermediate Similarity	NPC142838
0.7551	Intermediate Similarity	NPC116726
0.7549	Intermediate Similarity	NPC266955
0.7547	Intermediate Similarity	NPC102843
0.7528	Intermediate Similarity	NPC171148
0.7528	Intermediate Similarity	NPC69383
0.7528	Intermediate Similarity	NPC313179
0.7526	Intermediate Similarity	NPC472676
0.7526	Intermediate Similarity	NPC118011
0.7526	Intermediate Similarity	NPC472688
0.7526	Intermediate Similarity	NPC36668
0.75	Intermediate Similarity	NPC148685
0.75	Intermediate Similarity	NPC287079
0.75	Intermediate Similarity	NPC104120
0.75	Intermediate Similarity	NPC259286
0.75	Intermediate Similarity	NPC157895
0.75	Intermediate Similarity	NPC476245
0.7476	Intermediate Similarity	NPC472637
0.7476	Intermediate Similarity	NPC115899
0.7474	Intermediate Similarity	NPC187529
0.7474	Intermediate Similarity	NPC32037
0.7474	Intermediate Similarity	NPC255174
0.7451	Intermediate Similarity	NPC316598
0.7449	Intermediate Similarity	NPC134321
0.7449	Intermediate Similarity	NPC230332
0.7447	Intermediate Similarity	NPC169941
0.7447	Intermediate Similarity	NPC477786
0.7447	Intermediate Similarity	NPC477784
0.7447	Intermediate Similarity	NPC251475
0.7447	Intermediate Similarity	NPC477785
0.7423	Intermediate Similarity	NPC104560
0.7423	Intermediate Similarity	NPC58271
0.7423	Intermediate Similarity	NPC72397
0.7419	Intermediate Similarity	NPC116797
0.7419	Intermediate Similarity	NPC6663
0.7419	Intermediate Similarity	NPC470298
0.7404	Intermediate Similarity	NPC473424
0.74	Intermediate Similarity	NPC196227
0.74	Intermediate Similarity	NPC8993
0.7396	Intermediate Similarity	NPC316426
0.7396	Intermediate Similarity	NPC315395
0.7396	Intermediate Similarity	NPC470955
0.7396	Intermediate Similarity	NPC472985
0.7396	Intermediate Similarity	NPC472986
0.7391	Intermediate Similarity	NPC308038
0.7383	Intermediate Similarity	NPC264819
0.7374	Intermediate Similarity	NPC475806
0.7374	Intermediate Similarity	NPC472975
0.7368	Intermediate Similarity	NPC40687
0.7368	Intermediate Similarity	NPC476412
0.7363	Intermediate Similarity	NPC97173
0.7358	Intermediate Similarity	NPC85529
0.7358	Intermediate Similarity	NPC32006
0.7356	Intermediate Similarity	NPC136473
0.7353	Intermediate Similarity	NPC135685
0.7353	Intermediate Similarity	NPC470522
0.7347	Intermediate Similarity	NPC474918
0.7347	Intermediate Similarity	NPC472489
0.7347	Intermediate Similarity	NPC472971
0.7347	Intermediate Similarity	NPC123912
0.7347	Intermediate Similarity	NPC472970
0.734	Intermediate Similarity	NPC279186
0.734	Intermediate Similarity	NPC93590
0.7339	Intermediate Similarity	NPC474315
0.7333	Intermediate Similarity	NPC166018
0.7333	Intermediate Similarity	NPC249187
0.7333	Intermediate Similarity	NPC225665
0.7333	Intermediate Similarity	NPC169056
0.7333	Intermediate Similarity	NPC329345
0.7333	Intermediate Similarity	NPC475526
0.7333	Intermediate Similarity	NPC473624
0.7333	Intermediate Similarity	NPC247957
0.7333	Intermediate Similarity	NPC473283
0.7333	Intermediate Similarity	NPC95899
0.7327	Intermediate Similarity	NPC271195
0.7327	Intermediate Similarity	NPC134067
0.7327	Intermediate Similarity	NPC88310
0.7327	Intermediate Similarity	NPC280725
0.732	Intermediate Similarity	NPC141292
0.732	Intermediate Similarity	NPC220930
0.732	Intermediate Similarity	NPC272039
0.7315	Intermediate Similarity	NPC475065
0.7312	Intermediate Similarity	NPC172013
0.7312	Intermediate Similarity	NPC160582
0.73	Intermediate Similarity	NPC69454
0.7292	Intermediate Similarity	NPC109528
0.7292	Intermediate Similarity	NPC79573
0.7292	Intermediate Similarity	NPC476426
0.7292	Intermediate Similarity	NPC474853
0.7292	Intermediate Similarity	NPC179006
0.729	Intermediate Similarity	NPC472925
0.729	Intermediate Similarity	NPC330011
0.729	Intermediate Similarity	NPC329048
0.7283	Intermediate Similarity	NPC231739
0.7283	Intermediate Similarity	NPC478122
0.7282	Intermediate Similarity	NPC235464
0.7282	Intermediate Similarity	NPC471717
0.7282	Intermediate Similarity	NPC108368
0.7282	Intermediate Similarity	NPC166745
0.7282	Intermediate Similarity	NPC57079
0.7273	Intermediate Similarity	NPC128672
0.7273	Intermediate Similarity	NPC48010
0.7273	Intermediate Similarity	NPC475970
0.7263	Intermediate Similarity	NPC105173
0.7255	Intermediate Similarity	NPC471153
0.7253	Intermediate Similarity	NPC470525
0.7245	Intermediate Similarity	NPC292491
0.7245	Intermediate Similarity	NPC310752
0.7245	Intermediate Similarity	NPC229612
0.7245	Intermediate Similarity	NPC471722
0.7245	Intermediate Similarity	NPC473229
0.7245	Intermediate Similarity	NPC48107
0.7245	Intermediate Similarity	NPC471724
0.7245	Intermediate Similarity	NPC476796
0.7245	Intermediate Similarity	NPC7280
0.7238	Intermediate Similarity	NPC32577
0.7238	Intermediate Similarity	NPC293753
0.7238	Intermediate Similarity	NPC114540
0.7238	Intermediate Similarity	NPC155332
0.7234	Intermediate Similarity	NPC14151
0.7232	Intermediate Similarity	NPC64318
0.7228	Intermediate Similarity	NPC474882
0.7228	Intermediate Similarity	NPC181393
0.7228	Intermediate Similarity	NPC473162
0.7228	Intermediate Similarity	NPC474328
0.7228	Intermediate Similarity	NPC469406
0.7228	Intermediate Similarity	NPC217624
0.7228	Intermediate Similarity	NPC292793
0.7228	Intermediate Similarity	NPC23170
0.7222	Intermediate Similarity	NPC473482
0.7222	Intermediate Similarity	NPC318363
0.7222	Intermediate Similarity	NPC476802
0.7222	Intermediate Similarity	NPC89171
0.7222	Intermediate Similarity	NPC475418
0.7216	Intermediate Similarity	NPC222613
0.7216	Intermediate Similarity	NPC473226
0.7216	Intermediate Similarity	NPC198761
0.7216	Intermediate Similarity	NPC118648
0.7216	Intermediate Similarity	NPC475022
0.7212	Intermediate Similarity	NPC154072
0.7212	Intermediate Similarity	NPC198880
0.7207	Intermediate Similarity	NPC122056
0.7204	Intermediate Similarity	NPC281138
0.72	Intermediate Similarity	NPC172101
0.72	Intermediate Similarity	NPC473998
0.72	Intermediate Similarity	NPC233116
0.72	Intermediate Similarity	NPC63748
0.7196	Intermediate Similarity	NPC257353
0.7196	Intermediate Similarity	NPC166607
0.7196	Intermediate Similarity	NPC478052
0.7191	Intermediate Similarity	NPC95863
0.7188	Intermediate Similarity	NPC302360
0.7184	Intermediate Similarity	NPC21728
0.7184	Intermediate Similarity	NPC254496
0.7184	Intermediate Similarity	NPC320306

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 NPC78159 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	1568
0.2-0.3	3952
0.3-0.4	2452
0.4-0.5	647
0.5-0.6	281
0.6-0.7	59
0.7-0.8	5
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
0.809	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD8264	Approved
0.7129	Intermediate Similarity	NPD5779	Approved
0.7129	Intermediate Similarity	NPD5778	Approved
0.7113	Intermediate Similarity	NPD1696	Phase 3
0.7041	Intermediate Similarity	NPD4623	Approved
0.7041	Intermediate Similarity	NPD4519	Discontinued
0.7041	Intermediate Similarity	NPD3618	Phase 1
0.703	Intermediate Similarity	NPD6411	Approved
0.703	Intermediate Similarity	NPD6079	Approved
0.7018	Intermediate Similarity	NPD7115	Discovery
0.6939	Remote Similarity	NPD5363	Approved
0.6931	Remote Similarity	NPD5785	Approved
0.6916	Remote Similarity	NPD5211	Phase 2
0.69	Remote Similarity	NPD4518	Approved
0.6869	Remote Similarity	NPD5279	Phase 3
0.6869	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7515	Phase 2
0.6832	Remote Similarity	NPD5328	Approved
0.6832	Remote Similarity	NPD6101	Approved
0.6832	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4225	Approved
0.6789	Remote Similarity	NPD5141	Approved
0.6762	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5221	Approved
0.6762	Remote Similarity	NPD5222	Approved
0.6731	Remote Similarity	NPD7748	Approved
0.6729	Remote Similarity	NPD4696	Approved
0.6729	Remote Similarity	NPD5285	Approved
0.6729	Remote Similarity	NPD5286	Approved
0.6698	Remote Similarity	NPD5173	Approved
0.6698	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6635	Remote Similarity	NPD4202	Approved
0.6633	Remote Similarity	NPD3667	Approved
0.6633	Remote Similarity	NPD4270	Approved
0.6633	Remote Similarity	NPD4269	Approved
0.6606	Remote Similarity	NPD5225	Approved
0.6606	Remote Similarity	NPD5226	Approved
0.6606	Remote Similarity	NPD4633	Approved
0.6606	Remote Similarity	NPD5224	Approved
0.6604	Remote Similarity	NPD4697	Phase 3
0.6598	Remote Similarity	NPD4252	Approved
0.6598	Remote Similarity	NPD4695	Discontinued
0.6562	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5174	Approved
0.6545	Remote Similarity	NPD5175	Approved
0.6542	Remote Similarity	NPD4755	Approved
0.6538	Remote Similarity	NPD5284	Approved
0.6538	Remote Similarity	NPD7637	Suspended
0.6538	Remote Similarity	NPD5281	Approved
0.6509	Remote Similarity	NPD5210	Approved
0.6509	Remote Similarity	NPD4629	Approved
0.65	Remote Similarity	NPD3666	Approved
0.65	Remote Similarity	NPD3665	Phase 1
0.65	Remote Similarity	NPD3133	Approved
0.6491	Remote Similarity	NPD4634	Approved
0.646	Remote Similarity	NPD6881	Approved
0.646	Remote Similarity	NPD6899	Approved
0.6435	Remote Similarity	NPD8130	Phase 1
0.6435	Remote Similarity	NPD6650	Approved
0.6435	Remote Similarity	NPD6649	Approved
0.6422	Remote Similarity	NPD4700	Approved
0.6415	Remote Similarity	NPD7900	Approved
0.6415	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8297	Approved
0.6373	Remote Similarity	NPD4693	Phase 3
0.6373	Remote Similarity	NPD4690	Approved
0.6373	Remote Similarity	NPD4138	Approved
0.6373	Remote Similarity	NPD5786	Approved
0.6373	Remote Similarity	NPD5280	Approved
0.6373	Remote Similarity	NPD4688	Approved
0.6373	Remote Similarity	NPD5205	Approved
0.6373	Remote Similarity	NPD4694	Approved
0.6373	Remote Similarity	NPD4689	Approved
0.6373	Remote Similarity	NPD5690	Phase 2
0.6372	Remote Similarity	NPD5697	Approved
0.6364	Remote Similarity	NPD6898	Phase 1
0.6364	Remote Similarity	NPD5369	Approved
0.6348	Remote Similarity	NPD7102	Approved
0.6348	Remote Similarity	NPD7290	Approved
0.6348	Remote Similarity	NPD6883	Approved
0.6346	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4753	Phase 2
0.6321	Remote Similarity	NPD6399	Phase 3
0.6316	Remote Similarity	NPD5733	Approved
0.6316	Remote Similarity	NPD4729	Approved
0.6316	Remote Similarity	NPD4730	Approved
0.6316	Remote Similarity	NPD4058	Approved
0.6316	Remote Similarity	NPD6011	Approved
0.6316	Remote Similarity	NPD4687	Approved
0.6311	Remote Similarity	NPD7750	Discontinued
0.6293	Remote Similarity	NPD6847	Approved
0.6293	Remote Similarity	NPD6617	Approved
0.6293	Remote Similarity	NPD6869	Approved
0.6283	Remote Similarity	NPD5739	Approved
0.6283	Remote Similarity	NPD6675	Approved
0.6283	Remote Similarity	NPD7128	Approved
0.6283	Remote Similarity	NPD6402	Approved
0.6277	Remote Similarity	NPD5276	Approved
0.6275	Remote Similarity	NPD1694	Approved
0.6273	Remote Similarity	NPD7640	Approved
0.6273	Remote Similarity	NPD7639	Approved
0.6264	Remote Similarity	NPD7331	Phase 2
0.6263	Remote Similarity	NPD7332	Phase 2
0.6263	Remote Similarity	NPD7514	Phase 3
0.6262	Remote Similarity	NPD5282	Discontinued
0.6261	Remote Similarity	NPD6013	Approved
0.6261	Remote Similarity	NPD6372	Approved
0.6261	Remote Similarity	NPD6012	Approved
0.6261	Remote Similarity	NPD6014	Approved
0.6261	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD8039	Approved
0.625	Remote Similarity	NPD4754	Approved
0.6239	Remote Similarity	NPD6882	Approved
0.6238	Remote Similarity	NPD5331	Approved
0.6238	Remote Similarity	NPD5332	Approved
0.6226	Remote Similarity	NPD7983	Approved
0.6207	Remote Similarity	NPD5135	Approved
0.6207	Remote Similarity	NPD5251	Approved
0.6207	Remote Similarity	NPD5250	Approved
0.6207	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5249	Phase 3
0.6207	Remote Similarity	NPD5169	Approved
0.6207	Remote Similarity	NPD5247	Approved
0.6207	Remote Similarity	NPD5248	Approved
0.6204	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7638	Approved
0.6182	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD3668	Phase 3
0.6174	Remote Similarity	NPD7320	Approved
0.6174	Remote Similarity	NPD5168	Approved
0.6174	Remote Similarity	NPD5128	Approved
0.6162	Remote Similarity	NPD6683	Phase 2
0.6154	Remote Similarity	NPD3573	Approved
0.6154	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5127	Approved
0.6154	Remote Similarity	NPD5216	Approved
0.6154	Remote Similarity	NPD5217	Approved
0.6154	Remote Similarity	NPD5215	Approved
0.6148	Remote Similarity	NPD6054	Approved
0.6147	Remote Similarity	NPD7839	Suspended
0.614	Remote Similarity	NPD4768	Approved
0.614	Remote Similarity	NPD4767	Approved
0.6139	Remote Similarity	NPD5209	Approved
0.6139	Remote Similarity	NPD4223	Phase 3
0.6139	Remote Similarity	NPD4221	Approved
0.6132	Remote Similarity	NPD4096	Approved
0.6122	Remote Similarity	NPD4756	Discovery
0.6117	Remote Similarity	NPD5329	Approved
0.6105	Remote Similarity	NPD7151	Approved
0.6105	Remote Similarity	NPD7152	Approved
0.6105	Remote Similarity	NPD7150	Approved
0.6098	Remote Similarity	NPD8517	Approved
0.6098	Remote Similarity	NPD8515	Approved
0.6098	Remote Similarity	NPD8513	Phase 3
0.6098	Remote Similarity	NPD8516	Approved
0.6091	Remote Similarity	NPD6084	Phase 2
0.6091	Remote Similarity	NPD6083	Phase 2
0.6087	Remote Similarity	NPD5701	Approved
0.6078	Remote Similarity	NPD5362	Discontinued
0.6068	Remote Similarity	NPD6371	Approved
0.6061	Remote Similarity	NPD7145	Approved
0.6055	Remote Similarity	NPD5695	Phase 3
0.605	Remote Similarity	NPD4632	Approved
0.6048	Remote Similarity	NPD6370	Approved
0.604	Remote Similarity	NPD4139	Approved
0.604	Remote Similarity	NPD6902	Approved
0.604	Remote Similarity	NPD4692	Approved
0.6019	Remote Similarity	NPD4197	Approved
0.6017	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD4194	Approved
0.6	Remote Similarity	NPD4192	Approved
0.6	Remote Similarity	NPD4691	Approved
0.6	Remote Similarity	NPD5167	Approved
0.6	Remote Similarity	NPD4193	Approved
0.6	Remote Similarity	NPD7144	Approved
0.6	Remote Similarity	NPD7143	Approved
0.6	Remote Similarity	NPD4191	Approved
0.5984	Remote Similarity	NPD6335	Approved
0.5982	Remote Similarity	NPD6404	Discontinued
0.5981	Remote Similarity	NPD5207	Approved
0.598	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD6926	Approved
0.5979	Remote Similarity	NPD6924	Approved
0.5977	Remote Similarity	NPD4219	Approved
0.5968	Remote Similarity	NPD6015	Approved
0.5968	Remote Similarity	NPD6016	Approved
0.596	Remote Similarity	NPD5776	Phase 2
0.596	Remote Similarity	NPD6932	Approved
0.596	Remote Similarity	NPD6925	Approved
0.5952	Remote Similarity	NPD7492	Approved
0.595	Remote Similarity	NPD6868	Approved
0.5941	Remote Similarity	NPD6931	Approved
0.5941	Remote Similarity	NPD4819	Approved
0.5941	Remote Similarity	NPD4822	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