NPASS Compound

Natural Product: NPC313047

Natural Product ID	NPC313047
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(9S,9'r)-2,4,4',5,5'-Pentahydroxy-2',7-Dimethyl-9,9'-Bianthracene-10,10'(9H,9'h)-Dione
IUPAC Name	(10S)-10-[(9R)-4,5-dihydroxy-2-methyl-10-oxo-9H-anthracen-9-yl]-1,3,8-trihydroxy-6-methyl-10H-anthracen-9-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL518071
PubChem CID	44567184
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

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 59 64 0 0 0 0 0 0 0 0999 V2000 0.7004 1.1809 -4.3890 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2253 1.1162 -2.9981 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1485 2.0428 -2.5661 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6424 1.9914 -1.2793 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5803 2.9370 -0.8506 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1989 1.0006 -0.4318 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2561 0.0304 -0.8173 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7994 0.1222 -2.1002 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7925 -0.9977 0.1158 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7169 -1.1279 0.2705 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3456 -1.7553 -0.9241 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8613 -2.9866 -1.3564 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4048 -3.5976 -2.4610 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4398 -3.0341 -3.1864 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9217 -1.8175 -2.7618 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3611 -1.2010 -1.6328 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9565 0.0614 -1.2427 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8925 0.5766 -1.9014 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 0.6914 -0.0462 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3783 0.1289 0.6812 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9498 0.7608 1.8242 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5587 1.9560 2.2216 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0872 2.6300 3.4566 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5808 2.4926 1.4710 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0365 1.8874 0.3232 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0634 2.4235 -0.4329 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9572 -1.2090 -3.4517 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5009 -1.0300 1.4049 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4290 -0.0928 1.7937 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8082 0.9564 0.8922 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6640 1.8315 1.2500 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0643 -0.1353 3.0201 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0059 0.8414 3.3824 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7744 -1.1426 3.8974 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8538 -2.0987 3.5443 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2186 -2.0456 2.3055 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5802 -3.1062 4.4499 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4840 0.6929 -5.0346 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5092 2.2193 -4.7149 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1846 0.5293 -4.4444 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5203 2.8430 -3.2162 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3527 3.6742 -0.2066 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0996 -0.5642 -2.5448 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1570 -1.9821 -0.3935 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9353 -1.8403 1.1274 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0587 -3.4999 -0.8451 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0002 -4.5686 -2.7763 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8450 -3.5485 -4.0577 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1744 0.4016 2.4803 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0038 2.4727 3.5245 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5543 2.0725 4.3106 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4008 3.6783 3.4558 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0602 3.4198 1.7694 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9093 3.0054 -1.2508 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7634 -1.7092 -3.7679 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8510 0.4884 3.8148 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2934 -1.1458 4.8553 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5138 -2.8444 2.1239 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7826 -4.0761 4.3164 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 4 6 2 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 22 24 1 0 24 25 2 0 25 26 1 0 15 27 1 0 9 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 29 32 1 0 32 33 1 0 32 34 2 0 34 35 1 0 35 36 2 0 35 37 1 0 8 2 1 0 20 10 1 0 36 28 1 0 30 6 1 0 16 11 1 0 25 19 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 5 42 1 0 8 43 1 0 9 44 1 6 10 45 1 1 12 46 1 0 13 47 1 0 14 48 1 0 21 49 1 0 23 50 1 0 23 51 1 0 23 52 1 0 24 53 1 0 26 54 1 0 27 55 1 0 33 56 1 0 34 57 1 0 36 58 1 0 37 59 1 0 M END

Standard InCHIKey	VUUFXTUVVIEIMH-RPWUZVMVSA-N
Standard InCHI	InChI=1S/C30H22O7/c1-12-6-16-23(15-4-3-5-19(32)25(15)29(36)26(16)20(33)8-12)24-17-7-13(2)9-21(34)27(17)30(37)28-18(24)10-14(31)11-22(28)35/h3-11,23-24,31-35H,1-2H3/t23-,24+/m1/s1
SMILES	Cc1cc(O)c2c(c1)[C@H]([C@@H]1c3cccc(c3C(=O)c3c1cc(C)cc3O)O)c1c(C2=O)c(O)cc(c1)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
NPO21244	Delphinium nuttallianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978210]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087602]
NPO32935	rhamnus nepalensis	Species	Rhamnaceae	Eukaryota	Leaves	Pa Co, Mai Chau, Hoa Binh Province, 150 km west of Hanoi, Vietnam	1995-Nov	PMID[11575949]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932124]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	stem	n.a.	PMID[12932124]
NPO21244	Delphinium nuttallianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19012276]
NPO19996	Caulerpa peltata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25593390]
NPO27164	Aspergillus alliaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29517220]
NPO27164	Aspergillus alliaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3417561]
NPO27873	Ravenia spectabilis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34570617]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10359	Chaiturus marrubiastrum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19818	Jacquemontia paniculata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14248	Mandragora autumnalis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20223	Rosa pomifera	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11580	Onobrychis arenaria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27140	Amanita phalloides	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22675	Helichrysum chionosphaerum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27164	Aspergillus alliaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18144	Metrodorea nigra	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19037	Senecio praecox	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20422	Albizia myriophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21244	Delphinium nuttallianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27873	Ravenia spectabilis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26393.1	Petunia integrifolia subsp. inflata	Subspecies	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17018	Salvia greggii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20753	Grangea maderaspatana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19050	Garcinia polyantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21691	Dillenia indica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13454	Amphorogyne spicata	Species	Amphorogynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26917	Quercus rubra	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16142	Verbascum thapsiforme	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15422	Carduus tenuiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20144	Lespedeza tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26972	Baccharis potosina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18287	Penicillium bilaiae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20144	Lespedeza tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26917	Quercus rubra	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20144	Lespedeza tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26917	Quercus rubra	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17018	Salvia greggii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3980	Frangula purshiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19050	Garcinia polyantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27140	Amanita phalloides	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13754	Tanacetum coccineum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21691	Dillenia indica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2228	Photinia serratifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20947	Tagetes filifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12108	Aizopsis selskiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27454	Turbo cornutus	Species	Turbinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13754	Tanacetum coccineum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19512	Gleichenia quadripartita	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16572	Rhododendron dahuricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21691	Dillenia indica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20144	Lespedeza tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21244	Delphinium nuttallianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13454	Amphorogyne spicata	Species	Amphorogynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20560	Polyporus betulinus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19818	Jacquemontia paniculata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17018	Salvia greggii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20625	Delphinium virgatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21376	Lupinus corymbosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18867	Stephanitis takeyai	Species	Tingidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14800	Oophaga granulifera	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19037	Senecio praecox	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11580	Onobrychis arenaria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17856	Anaphalis lactea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18144	Metrodorea nigra	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19996	Caulerpa peltata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14932.1	Dalbergia lanceolaria subsp. paniculata	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21564	Senecio behnii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2228	Photinia serratifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14248	Mandragora autumnalis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13246	Pinalia stricta	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26393.1	Petunia integrifolia subsp. inflata	Subspecies	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20844	Sphaerella rosigena	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17568	Balanophora laxiflora	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19232	Anchusa azurea	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19671	Dipsacus azureus	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22675	Helichrysum chionosphaerum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15422	Carduus tenuiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19395	Nepeta granatensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20223	Rosa pomifera	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20753	Grangea maderaspatana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27164	Aspergillus alliaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16142	Verbascum thapsiforme	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24407	Bipolaris heveae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26972	Baccharis potosina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18287	Penicillium bilaiae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21112	Chaetomium carinthiacum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10216	Leptocereus quadricostatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27873	Ravenia spectabilis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20353	Degenia velebitica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17822	Fridericia triplinervia	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27564	Stevia berlandieri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10359	Chaiturus marrubiastrum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10239	Magnolia figo	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20422	Albizia myriophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27737	Penicillium shearii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27140	Amanita phalloides	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19913	Rhynchophorus ferrugineus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26917	Quercus rubra	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24629	Achromobacter denitrificans	Species	Alcaligenaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3980	Frangula purshiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27790	Delia arenicola	Species	Anthomyiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19050	Garcinia polyantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4132	Cranfillia fluviatilis	Species	Blechnaceae	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	1

Activity Type	# Activity
Cell line	1

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
NPT91	Cell line	KB	Homo sapiens	IC50	=	1400.0	nM	PMID[11575949]

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 NPC313047 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	30597
0.1-0.2	17484
0.2-0.3	1598
0.3-0.4	126
0.4-0.5	42
0.5-0.6	3
0.6-0.7	0
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474203
1.0	High Similarity	NPC451542
1.0	High Similarity	NPC295712
0.8333	Intermediate Similarity	NPC161964
0.8333	Intermediate Similarity	NPC287604
0.8095	Intermediate Similarity	NPC293545
0.8095	Intermediate Similarity	NPC174905
0.5306	Remote Similarity	NPC282923
0.5102	Remote Similarity	NPC254847
0.5098	Remote Similarity	NPC173978

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC313047 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5546
0.1-0.2	3520
0.2-0.3	79
0.3-0.4	3
0.4-0.5	1
0.5-0.6	1
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
0.5102	Remote Similarity	NPD1509	Clinical (unspecified phase)

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