NPASS Compound

Natural Product: NPC138990

Natural Product ID	NPC138990
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Oxytroflavoside B
IUPAC Name	(3S)-3-hydroxy-5-[(2S,3R,4S,5S,6R)-5-hydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxochromen-3-yl]oxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-4-yl]oxy-3-methyl-5-oxopentanoic acid
Synonyms	Oxytroflavoside B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2071418
PubChem CID	60200066
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

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 93 97 0 0 0 0 0 0 0 0999 V2000 0.8990 -4.9569 -1.3122 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3457 -4.0926 -1.3106 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3980 -4.8510 -0.5225 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6736 -4.0592 -0.3590 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3896 -2.6751 -0.9617 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1526 -2.1595 -0.3255 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0125 -2.8919 -0.7037 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9752 -0.8113 -0.5638 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8740 -0.1104 0.5982 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7480 1.0841 0.7545 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4799 1.6680 2.1511 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0120 1.9574 2.2953 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2877 2.3766 3.7179 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4297 3.5326 4.0638 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7444 0.8064 2.0461 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5630 0.3666 0.7364 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5010 -0.6297 0.4260 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6465 -0.2969 -0.2502 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5671 -0.1654 -1.6429 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4674 -0.3591 -2.2423 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7059 0.1757 -2.3277 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6588 0.3143 -3.6950 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7800 0.6579 -4.4221 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9668 0.8644 -3.7554 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0483 0.7338 -2.3873 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8903 0.3821 -1.6668 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9185 0.2483 -0.3881 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8391 -0.0867 0.3474 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0592 -0.2014 1.7727 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2401 -0.8270 2.6589 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4883 -0.8688 4.0393 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5985 -0.2625 4.5506 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4370 0.3740 3.6611 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1983 0.4163 2.3231 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8768 -0.2831 5.9127 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0758 1.2079 -4.5076 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3127 1.4272 -3.8496 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4308 0.0957 -4.3406 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8744 0.7385 3.1204 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1169 0.8654 0.6251 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9772 1.5182 -0.2330 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5093 2.4028 -0.9859 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4296 1.2176 -0.3014 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1464 2.0616 -1.3036 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6091 1.8766 -2.7043 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1828 3.5290 -0.9957 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8595 3.8254 0.2795 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3677 2.9469 1.0049 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9678 5.1430 0.7508 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5046 1.6577 -1.3593 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4642 -1.8736 -0.6354 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9112 -3.9014 0.9952 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7206 -5.9909 -1.2873 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7664 -5.8829 -1.8855 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0572 -5.2642 -0.2434 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8059 -4.3905 -1.6039 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6616 -3.9849 -2.3681 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0220 -5.1945 0.4434 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5273 -4.5228 -0.8931 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3062 -2.7973 -2.0664 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2148 -2.3094 0.7712 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0066 -0.8120 1.4765 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3910 1.8928 0.0522 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0531 2.5902 2.3157 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2692 2.7987 1.6455 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3840 2.6330 3.7835 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0684 1.5635 4.4396 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4332 4.1614 3.3015 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7158 1.2207 0.0412 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7307 0.7664 -5.5182 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9612 0.8891 -1.8401 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3594 -1.3422 2.2952 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7704 -1.3948 4.6653 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3207 0.8496 4.1114 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8831 0.9287 1.6554 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3737 -1.0705 6.3341 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1298 2.0987 -3.0037 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7339 0.4551 -3.4852 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0405 1.8715 -4.5818 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4574 -0.0929 -5.3271 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7870 0.4251 2.8784 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5621 0.1317 -0.5930 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8113 1.2818 0.7244 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4467 2.0846 -3.4221 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7991 2.6333 -2.9192 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2669 0.8491 -2.9034 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7537 3.9987 -1.8539 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1821 4.0158 -1.0161 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1475 5.3425 1.7214 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7492 1.1511 -0.5438 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8150 -1.4016 -1.4380 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8380 -3.5634 1.1661 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1225 -6.7266 -1.0029 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 0 13 14 1 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 32 35 1 0 24 36 1 0 36 37 1 0 22 38 1 0 11 39 1 0 10 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 43 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 47 48 2 0 47 49 1 0 44 50 1 6 5 51 1 0 4 52 1 0 3 53 1 0 7 2 1 0 16 9 1 0 28 18 2 0 34 29 1 0 26 21 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 6 3 58 1 1 4 59 1 6 5 60 1 6 6 61 1 1 9 62 1 1 10 63 1 6 11 64 1 1 12 65 1 6 13 66 1 0 13 67 1 0 14 68 1 0 16 69 1 6 23 70 1 0 25 71 1 0 30 72 1 0 31 73 1 0 33 74 1 0 34 75 1 0 35 76 1 0 37 77 1 0 37 78 1 0 37 79 1 0 38 80 1 0 39 81 1 0 43 82 1 0 43 83 1 0 45 84 1 0 45 85 1 0 45 86 1 0 46 87 1 0 46 88 1 0 49 89 1 0 50 90 1 0 51 91 1 0 52 92 1 0 53 93 1 0 M END

Standard InCHIKey	WWLLPHKIYLKMTO-IJDJMGSLSA-N
Standard InCHI	InChI=1S/C34H40O19/c1-13-23(41)26(44)27(45)32(48-13)53-31-29(51-21(40)11-34(2,46)10-20(38)39)24(42)19(12-35)50-33(31)52-30-25(43)22-17(37)8-16(47-3)9-18(22)49-28(30)14-4-6-15(36)7-5-14/h4-9,13,19,23-24,26-27,29,31-33,35-37,41-42,44-46H,10-12H2,1-3H3,(H,38,39)/t13-,19+,23-,24-,26+,27+,29-,31+,32-,33-,34-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H]([C@@H](CO)O[C@H]1Oc1c(=O)c2c(cc(cc2oc1c1ccc(cc1)O)OC)O)O)OC(=O)C[C@](C)(CC(=O)O)O)O)O)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
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1007/s11418-005-0009-z]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691704]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378371]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643065]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18257536]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19177635]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19433363]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	Sunan County, Gansu Province, China	2006-JUN	PMID[20684529]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	stem	n.a.	PMID[22032651]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22032651]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	whole plant	Guide County, Qinghai Province, China	2008-AUG	PMID[22775441]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30219526]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32705864]
NPO6065	Brassica carinata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36599374]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4536	Remirea maritima	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3151	Solanum lanceolatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7032	Marasmiellus troyanus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4123	Trididemnum cyanophorum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8938	Halobacillus litoralis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7418	Eucalyptus resinifera	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4901	Arnica mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5857	Achlya heterosexualis	Species	Saprolegniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6807	Ranunculus asiaticus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6065	Brassica carinata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4901	Arnica mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2439	Diplopterygium glaucum	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4123	Trididemnum cyanophorum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3151	Solanum lanceolatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2670	Maytenus chuchuhuasha	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6807	Ranunculus asiaticus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3838	Chrysosporum ovalisporum	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO593	Wikstroemia viridiflora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13474	Euphrasia genargentea	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8938	Halobacillus litoralis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6065	Brassica carinata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9594	Lysimachia fordiana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9737	Ampelocera edentula	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5086	Alternaria macrospora	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7032	Marasmiellus troyanus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4536	Remirea maritima	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21472	Pterolobium hexapetalum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9998	Abies excelsa	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10038.1	Abies pinsapo var. marocana	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9091	Orthosiphon spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5857	Achlya heterosexualis	Species	Saprolegniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1293	Streptomyces matensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7418	Eucalyptus resinifera	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10132	Schizophyllum lobatum	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9867	Ixeris debilis	Species	Asteraceae	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
Inhibition	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
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	<	5.0	%	PMID[22775441]

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 NPC138990 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	11181
0.1-0.2	33930
0.2-0.3	4026
0.3-0.4	372
0.4-0.5	292
0.5-0.6	41
0.6-0.7	9
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8396	Intermediate Similarity	NPC175429
0.7477	Intermediate Similarity	NPC209550
0.6827	Remote Similarity	NPC240306
0.6789	Remote Similarity	NPC121703
0.6404	Remote Similarity	NPC277532
0.6325	Remote Similarity	NPC480445
0.6239	Remote Similarity	NPC32641
0.6239	Remote Similarity	NPC256188
0.6182	Remote Similarity	NPC142142
0.6139	Remote Similarity	NPC46420
0.6091	Remote Similarity	NPC35119
0.595	Remote Similarity	NPC480444
0.5905	Remote Similarity	NPC116458
0.5905	Remote Similarity	NPC246943
0.5897	Remote Similarity	NPC25523
0.5818	Remote Similarity	NPC186816
0.5784	Remote Similarity	NPC249281
0.5766	Remote Similarity	NPC64425
0.5586	Remote Similarity	NPC150164
0.5577	Remote Similarity	NPC297987
0.5556	Remote Similarity	NPC14187
0.5556	Remote Similarity	NPC276377
0.5524	Remote Similarity	NPC271692
0.5495	Remote Similarity	NPC163242
0.5495	Remote Similarity	NPC272068
0.5398	Remote Similarity	NPC470444
0.5391	Remote Similarity	NPC72016
0.5372	Remote Similarity	NPC480441
0.536	Remote Similarity	NPC470717
0.5321	Remote Similarity	NPC605784
0.5317	Remote Similarity	NPC470720
0.5315	Remote Similarity	NPC473682
0.5299	Remote Similarity	NPC220173
0.5246	Remote Similarity	NPC164704
0.521	Remote Similarity	NPC602448
0.5189	Remote Similarity	NPC289667
0.5175	Remote Similarity	NPC65003
0.514	Remote Similarity	NPC158674
0.5138	Remote Similarity	NPC611303
0.5135	Remote Similarity	NPC476215
0.5124	Remote Similarity	NPC203145
0.5122	Remote Similarity	NPC470715
0.5082	Remote Similarity	NPC473072
0.5079	Remote Similarity	NPC295625
0.5077	Remote Similarity	NPC262222
0.5044	Remote Similarity	NPC251417
0.5043	Remote Similarity	NPC12013
0.5043	Remote Similarity	NPC155877
0.5043	Remote Similarity	NPC11432
0.5043	Remote Similarity	NPC477613
0.5042	Remote Similarity	NPC195257
0.504	Remote Similarity	NPC470716

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC138990 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3677
0.1-0.2	5379
0.2-0.3	87
0.3-0.4	2
0.4-0.5	4
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
0.5169	Remote Similarity	NPD7251	Phase 2

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