NPASS Compound

Natural Product: NPC12640

Natural Product ID	NPC12640
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Grifolin
IUPAC Name	5-methyl-2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzene-1,3-diol
Synonyms	Grifolin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL487804
PubChem CID	5372312
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

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 56 56 0 0 0 0 0 0 0 0999 V2000 -5.9286 0.4708 2.1177 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0270 0.5385 0.6340 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0882 0.0339 -0.1570 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2266 0.1233 -1.6219 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0698 0.8998 -2.2510 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7889 0.1797 -1.9199 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8205 0.7548 -1.2421 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5775 0.0394 -0.9271 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3404 -0.0666 0.5747 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9330 -0.8000 0.8156 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9620 -0.2574 1.4681 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2213 -0.9593 1.7156 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4195 -0.3430 1.1435 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4537 0.8034 0.3867 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6551 1.3146 -0.1168 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8398 0.6897 0.1274 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1513 1.1805 -0.3782 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8149 -0.4646 0.8881 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6297 -0.9670 1.3836 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7122 -2.1382 2.1404 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2730 1.4507 0.1272 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1077 -2.1920 0.3281 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6419 -1.2161 -2.3831 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2285 1.1998 0.0311 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8913 0.1526 2.5324 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1339 -0.2564 2.3924 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6395 1.4436 2.5702 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2272 -0.4405 0.3290 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1805 0.6306 -1.8574 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2999 -0.8942 -2.0559 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2443 0.9529 -3.3375 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0619 1.9245 -1.8420 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9785 1.7911 -0.9212 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6321 -0.9937 -1.3270 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3233 0.5073 -1.3574 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1659 -0.6877 0.9792 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3617 0.8984 1.0823 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8460 0.7572 1.8308 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2031 -2.0265 1.3638 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4068 -1.0525 2.8265 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6350 2.2214 -0.7086 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5770 0.3824 -1.0342 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8686 1.2906 0.4673 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0240 2.1322 -0.9142 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7367 -0.9617 1.0850 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6011 -2.1814 3.1279 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9827 1.5385 -0.8391 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2745 -2.5168 -0.3176 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0413 -2.1858 -0.3047 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2874 -2.9189 1.1285 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4789 -1.8450 -1.4668 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5547 -1.5751 -2.9108 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7355 -1.3206 -3.0091 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9333 2.0510 -0.6043 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9418 1.5239 0.8150 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7817 0.4825 -0.6070 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 16 18 1 0 18 19 2 0 19 20 1 0 14 21 1 0 10 22 1 0 6 23 1 0 2 24 1 0 19 13 1 0 1 25 1 0 1 26 1 0 1 27 1 0 3 28 1 0 4 29 1 0 4 30 1 0 5 31 1 0 5 32 1 0 7 33 1 0 8 34 1 0 8 35 1 0 9 36 1 0 9 37 1 0 11 38 1 0 12 39 1 0 12 40 1 0 15 41 1 0 17 42 1 0 17 43 1 0 17 44 1 0 18 45 1 0 20 46 1 0 21 47 1 0 22 48 1 0 22 49 1 0 22 50 1 0 23 51 1 0 23 52 1 0 23 53 1 0 24 54 1 0 24 55 1 0 24 56 1 0 M END

Standard InCHIKey	PZHNKNRPGLTZPO-VZRGJMDUSA-N
Standard InCHI	InChI=1S/C22H32O2/c1-16(2)8-6-9-17(3)10-7-11-18(4)12-13-20-21(23)14-19(5)15-22(20)24/h8,10,12,14-15,23-24H,6-7,9,11,13H2,1-5H3/b17-10+,18-12+
SMILES	CC(=CCC/C(=C/CC/C(=C/Cc1c(cc(C)cc1O)O)/C)/C)C

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
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1007/BF02329610]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1023/A:1025674116183]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1324982]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[13465274]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270561]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1536925]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180822]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17512094]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19376614]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[21435874]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	seed	n.a.	PMID[24225786]
NPO40323	Rhododendron nyingchiense	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30067363]
NPO6415	Juniperus excelsa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34203980]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3509958]
NPO21029	Euphorbia prostrata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36447306]
NPO6415	Juniperus excelsa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38330006]
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39073007]
NPO17403	Peperomia galioides	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7769398]
NPO17403	Peperomia galioides	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759169]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4274	Alcyonium utinomii	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5584	Aldisa sanguinea	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3554	Aonidiella aurantii	Species	Diaspididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18993	Araiostegiella perdurans	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5975	Aspergillus carneus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25760	Aspergillus striatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1242	Balanops australiana	Species	Balanopaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6231	Cortinarius odoratus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7449	Eleutherobia albiflora	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7007	Eucalyptus jenseni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO849	Euonymus tingens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15487	Gymnopus confluens	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2250	Hylocomium splendens	Species	Hylocomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO295	Kokoona reflexa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7760	Macrolepiota neomastoidea	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3956	Maesa ramentacea	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1390	Melolontha melolontha	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2993	Nototodarus sloanii	Species	Ommastrephidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8058	Pluchea odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1489	Pseudoplexaura flagellosa	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7606	Salacia lehmbachii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4949	Salvia yosgadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3743	Sideritis brevibracteata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5261	Sideroxylon cubense	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3408	Viguiera decurrens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8517	Adenia hastata	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5371	Ainsliaea fragrans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10626	Elsholtzia oldhami	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21029	Euphorbia prostrata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14844	Eurotia ceratoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6415	Juniperus excelsa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4414	Lilium lancifolium	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5198	Menegazzia terebrata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10962	Parsonsia spiralis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17403	Peperomia galioides	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7187	Polyporus dispansus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO40323	Rhododendron nyingchiense	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8897	Streptomyces flavogriseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4414	Lilium lancifolium	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4414	Lilium lancifolium	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4414	Lilium lancifolium	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO849	Euonymus tingens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2993	Nototodarus sloanii	Species	Ommastrephidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6231	Cortinarius odoratus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3956	Maesa ramentacea	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7606	Salacia lehmbachii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7007	Eucalyptus jenseni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5261	Sideroxylon cubense	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2250	Hylocomium splendens	Species	Hylocomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO295	Kokoona reflexa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5975	Aspergillus carneus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18993	Araiostegiella perdurans	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15487	Gymnopus confluens	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4949	Salvia yosgadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3743	Sideritis brevibracteata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7449	Eleutherobia albiflora	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8058	Pluchea odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1390	Melolontha melolontha	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25760	Aspergillus striatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5584	Aldisa sanguinea	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1242	Balanops australiana	Species	Balanopaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3554	Aonidiella aurantii	Species	Diaspididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4414	Lilium lancifolium	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7760	Macrolepiota neomastoidea	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5198	Menegazzia terebrata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4274	Alcyonium utinomii	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3408	Viguiera decurrens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1489	Pseudoplexaura flagellosa	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10626	Elsholtzia oldhami	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7187	Polyporus dispansus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6415	Juniperus excelsa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5371	Ainsliaea fragrans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10962	Parsonsia spiralis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21029	Euphorbia prostrata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8517	Adenia hastata	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8897	Streptomyces flavogriseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14844	Eurotia ceratoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17403	Peperomia galioides	Species	Piperaceae	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	6
Activity	1

Activity Type	# Activity
Individual protein	3
Single protein	2
Others	1
Organism	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	5700.0	nM	PMID[30067363]
NPT740	Individual protein	Beta-secretase 1	Homo sapiens	IC50	=	6100.0	nM	PMID[34100599]
NPT30107	Single protein	Amyloid-beta A4 protein	Homo sapiens	IC50	=	148800.0	nM	PMID[34100599]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	68.0	%	PMID[7769398]
NPT2	Others	Unspecified	n.a.	IC50	=	81.6	uL	PMID[15270561]

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 NPC12640 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	25634
0.1-0.2	21615
0.2-0.3	2131
0.3-0.4	347
0.4-0.5	94
0.5-0.6	19
0.6-0.7	16
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
0.7111	Intermediate Similarity	NPC99836
0.6667	Remote Similarity	NPC201662
0.6531	Remote Similarity	NPC483761
0.6531	Remote Similarity	NPC166995
0.6522	Remote Similarity	NPC263753
0.6444	Remote Similarity	NPC477685
0.6383	Remote Similarity	NPC102384
0.6275	Remote Similarity	NPC180261
0.625	Remote Similarity	NPC33728
0.625	Remote Similarity	NPC488443
0.625	Remote Similarity	NPC606098
0.6122	Remote Similarity	NPC144343
0.6087	Remote Similarity	NPC260775
0.6087	Remote Similarity	NPC130756
0.6087	Remote Similarity	NPC70677
0.6087	Remote Similarity	NPC12931
0.6	Remote Similarity	NPC479053
0.5882	Remote Similarity	NPC600345
0.566	Remote Similarity	NPC24125
0.5652	Remote Similarity	NPC152097
0.5625	Remote Similarity	NPC91105
0.5577	Remote Similarity	NPC39029
0.5306	Remote Similarity	NPC76400
0.5294	Remote Similarity	NPC600668
0.5192	Remote Similarity	NPC246967
0.5192	Remote Similarity	NPC65761
0.5185	Remote Similarity	NPC194579
0.5185	Remote Similarity	NPC474890
0.5185	Remote Similarity	NPC273282
0.5098	Remote Similarity	NPC324362
0.5094	Remote Similarity	NPC472029
0.5091	Remote Similarity	NPC477569
0.5088	Remote Similarity	NPC37299
0.5088	Remote Similarity	NPC602136
0.5085	Remote Similarity	NPC483756
0.5085	Remote Similarity	NPC609757

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC12640 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6327
0.1-0.2	2769
0.2-0.3	45
0.3-0.4	9
0.4-0.5	0
0.5-0.6	0
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
		NPD

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