NPASS Compound

Natural Product: NPC152615

Natural Product ID	NPC152615
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta-O-(Beta-D-Diginosyl)-8,14-Dihydroxy-5Beta,14Beta-Card-20(22)-Dienolide
IUPAC Name	3-[(3S,5R,8S,9R,10S,13R,14R,17R)-8,14-dihydroxy-3-[(2R,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-2,3,4,5,6,7,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL229260
PubChem CID	44425148
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 84 89 0 0 0 0 0 0 0 0999 V2000 6.2629 -1.5748 -0.9356 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5008 -0.1140 -1.1833 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3610 0.5427 -0.1344 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6132 0.4854 1.1588 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1435 0.6148 1.0274 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6254 0.9853 -0.3181 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3920 0.6359 -1.3919 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 0.3765 -0.4773 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4106 1.3128 -0.6544 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7020 1.1925 -1.9847 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2321 0.9900 -1.8207 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1428 -0.1553 -0.9045 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2505 -1.4318 -1.6437 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5560 -0.0154 0.4027 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2710 -0.0176 1.6190 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5339 -0.7623 1.6425 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0770 -1.1760 0.2962 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6268 -0.1091 -0.6782 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4569 -0.2341 -1.9046 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8492 0.2854 -1.5090 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4083 -0.3905 -0.3182 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7003 -1.0992 -0.7581 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8111 0.5191 0.8129 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9728 -0.4489 1.9525 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1565 -1.6820 1.6177 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5274 -1.4496 0.2822 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7541 -2.6164 -0.4879 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0126 1.3241 0.5432 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1901 1.3172 1.1496 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0973 2.2848 0.5532 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2950 2.5405 0.8824 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4047 2.8989 -0.4696 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1196 2.3406 -0.5163 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3650 -2.3377 -0.0337 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3548 1.2981 0.4141 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9266 -0.7429 1.7652 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6539 -0.5856 2.9297 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5766 -0.1170 0.0101 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9799 -2.0421 -1.9240 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4486 -1.8052 -0.2517 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2370 -2.0397 -0.6742 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1088 -0.0633 -2.1365 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4798 1.6016 -0.4290 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0647 1.2775 1.8256 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8157 1.4246 1.7466 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6228 -0.3019 1.4210 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4681 2.0802 -0.3795 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8576 2.3264 -0.6261 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8115 2.1308 -2.6030 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2232 0.4132 -2.5572 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1566 0.7396 -2.8524 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2064 1.9394 -1.4555 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0038 -1.2118 -2.4560 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7609 -2.1553 -0.9805 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6131 -1.8715 -2.1936 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3547 -0.8160 0.4259 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3809 -0.4027 2.4633 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4870 1.0413 1.9599 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3508 -0.2073 2.1505 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4357 -1.7172 2.2405 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8569 0.8677 -0.2024 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5644 -1.2834 -2.2502 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1553 0.4004 -2.7557 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5299 0.2506 -2.3874 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6861 1.3600 -1.2759 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0063 -1.8386 -0.0032 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4214 -1.6895 -1.6719 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4624 -0.3646 -1.0254 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9724 1.1979 1.0883 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0348 -0.7004 2.1510 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6139 0.0313 2.9077 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8738 -2.5384 1.5909 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4573 -1.8951 2.4329 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3538 -3.2444 -0.0358 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4853 0.6964 1.9793 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3822 3.1456 -0.3197 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9939 1.9383 -1.5424 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8751 -3.0089 -0.4993 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8703 1.3172 1.3967 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7080 2.1745 0.3534 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5995 -0.0549 2.6444 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0944 -0.0252 3.6908 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9579 -1.5890 3.2673 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9480 -0.3724 -0.8754 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 23 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 17 34 1 6 14 35 1 0 4 36 1 0 36 37 1 0 3 38 1 0 7 2 1 0 35 9 1 0 18 12 1 0 26 21 1 0 33 28 1 0 26 17 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 6 3 43 1 6 4 44 1 1 5 45 1 0 5 46 1 0 6 47 1 1 9 48 1 6 10 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 13 53 1 0 13 54 1 0 13 55 1 0 14 56 1 1 15 57 1 0 15 58 1 0 16 59 1 0 16 60 1 0 18 61 1 1 19 62 1 0 19 63 1 0 20 64 1 0 20 65 1 0 22 66 1 0 22 67 1 0 22 68 1 0 23 69 1 1 24 70 1 0 24 71 1 0 25 72 1 0 25 73 1 0 27 74 1 0 29 75 1 0 33 76 1 0 33 77 1 0 34 78 1 0 35 79 1 0 35 80 1 0 37 81 1 0 37 82 1 0 37 83 1 0 38 84 1 0 M END

Standard InCHIKey	UZWLNBWIIKVXSW-QFUJVLJYSA-N
Standard InCHI	InChI=1S/C30H46O8/c1-17-26(32)22(35-4)15-25(37-17)38-20-6-9-27(2)19(14-20)5-11-29(33)23(27)8-10-28(3)21(7-12-30(28,29)34)18-13-24(31)36-16-18/h13,17,19-23,25-26,32-34H,5-12,14-16H2,1-4H3/t17-,19-,20+,21-,22-,23-,25+,26+,27+,28-,29+,30-/m1/s1
SMILES	C[C@@H]1[C@@H]([C@@H](C[C@@H](O1)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@]3([C@@H]2CC[C@]2(C)[C@H](CC[C@]32O)C2=CC(=O)OC2)O)C1)OC)O

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1038/ncomms4886]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11277760]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19731587]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37726667]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39382805]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO1607	Croton rhamnifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2361	Aconitum brevicalcaratum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3146	Ammodendron conollyi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO351	Cirsium dipsacolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6377	Cocculus diversifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8585	Verpa digitaliformis	Species	Morchellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1308	Veronica pectinata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15583	Tripodanthus acutifolius	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6776	Trifolium apertum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO715	Teucrium pestalozzae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5197	Streptomyces eurythermus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6974	Solanum racemigerum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20132	Scutellaria seleriana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7097	Rhynchosporium orthosporum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8840	Ptilidium ciliare	Species	Ptilidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4253	Viguiera annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4082	Ophiarthrum elegans	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8472	Knightia deplanchei	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5591	Fucus spiralis	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5980	Eria subsessilis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5591	Fucus spiralis	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20132	Scutellaria seleriana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO715	Teucrium pestalozzae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8472	Knightia deplanchei	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15583	Tripodanthus acutifolius	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8840	Ptilidium ciliare	Species	Ptilidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4082	Ophiarthrum elegans	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2361	Aconitum brevicalcaratum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6776	Trifolium apertum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5197	Streptomyces eurythermus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO351	Cirsium dipsacolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8585	Verpa digitaliformis	Species	Morchellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6377	Cocculus diversifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7097	Rhynchosporium orthosporum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6974	Solanum racemigerum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1607	Croton rhamnifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5980	Eria subsessilis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3146	Ammodendron conollyi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4253	Viguiera annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1308	Veronica pectinata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10021	Nerium oleander	Species	Apocynaceae	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	Organism Name	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	5
Activity	3

Activity Type	# Activity
Cell line	5
Others	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1475	Cell line	WI-38 VA13	Homo sapiens	IC50	=	1600000.0	nM	PMID[17595134]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	4700000.0	nM	PMID[17595134]
NPT81	Cell line	A549	Homo sapiens	IC50	=	5900.0	nM	PMID[17595134]
NPT81	Cell line	A549	Homo sapiens	IC50	=	6000.0	nM	PMID[17595134]
NPT81	Cell line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[17595134]
NPT2	Others	Unspecified	n.a.	Activity	=	112.0	%	PMID[17595134]
NPT2	Others	Unspecified	n.a.	Activity	=	107.0	%	PMID[17595134]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC152615 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	14154
0.1-0.2	31429
0.2-0.3	3961
0.3-0.4	150
0.4-0.5	128
0.5-0.6	21
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7284	Intermediate Similarity	NPC84949
0.7284	Intermediate Similarity	NPC480562
0.7284	Intermediate Similarity	NPC74945
0.7284	Intermediate Similarity	NPC31354
0.7284	Intermediate Similarity	NPC69576
0.6512	Remote Similarity	NPC483822
0.6353	Remote Similarity	NPC99080
0.6207	Remote Similarity	NPC290693
0.6163	Remote Similarity	NPC34390
0.6023	Remote Similarity	NPC484212
0.6023	Remote Similarity	NPC180079
0.5934	Remote Similarity	NPC103534
0.5934	Remote Similarity	NPC44899
0.5934	Remote Similarity	NPC304260
0.5934	Remote Similarity	NPC29639
0.5914	Remote Similarity	NPC603096
0.5778	Remote Similarity	NPC484202
0.5568	Remote Similarity	NPC471633
0.5556	Remote Similarity	NPC199428
0.5556	Remote Similarity	NPC109448
0.5556	Remote Similarity	NPC310341
0.5435	Remote Similarity	NPC93883
0.5393	Remote Similarity	NPC99620
0.5376	Remote Similarity	NPC268326
0.5376	Remote Similarity	NPC153085
0.5306	Remote Similarity	NPC55532
0.5275	Remote Similarity	NPC477580
0.5158	Remote Similarity	NPC72260
0.5155	Remote Similarity	NPC115349
0.5146	Remote Similarity	NPC329636
0.5109	Remote Similarity	NPC5311
0.5048	Remote Similarity	NPC475419

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC152615 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5942
0.1-0.2	3136
0.2-0.3	57
0.3-0.4	4
0.4-0.5	5
0.5-0.6	5
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5957	Remote Similarity	NPD8377	Phase 4
0.5604	Remote Similarity	NPD7516	Pre-clinical
0.5408	Remote Similarity	NPD8378	Pre-clinical
0.5408	Remote Similarity	NPD8379	Approved
0.5158	Remote Similarity	NPD8294	Phase 4

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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