NPASS Compound

Natural Product: NPC60249

Natural Product ID	NPC60249
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Subavenoside D
IUPAC Name	(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[5-(hydroxymethyl)-3-methoxy-7H-dibenzo[1,2-a:3',4'-d][7]annulen-2-yl]oxy]oxane-3,4,5-triol
Synonyms	Subavenoside D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2152483
PubChem CID	71461984
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic 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 57 60 0 0 0 0 0 0 0 0999 V2000 -5.5892 2.0510 -0.8866 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3345 1.1886 -1.9766 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4488 0.0747 -1.3968 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3261 0.6718 -0.9230 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5744 -0.1126 -0.0456 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3744 0.4979 0.1869 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0786 0.1144 0.0597 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8746 1.0822 0.4196 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1916 0.7528 0.3140 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6277 -0.4919 -0.1370 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7002 -1.4332 -0.4864 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3528 -1.1270 -0.3866 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5484 -2.0840 -0.7409 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1151 -3.3446 -1.1941 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0018 -0.9663 -0.3478 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0110 -0.1526 -0.6000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1256 1.3156 -0.7454 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3336 2.0633 0.2637 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0562 1.8183 0.7576 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4669 2.5800 1.7251 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1813 3.6564 2.2373 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4512 3.9188 1.7592 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0360 3.1279 0.7730 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2190 -2.4291 -0.2625 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6143 -2.6404 -0.4875 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4578 -0.1667 1.2205 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6040 -1.0528 0.8519 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2760 -0.6707 -0.4088 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7064 -1.8611 -1.0420 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5430 -1.1256 1.9040 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7431 -0.6571 2.2934 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7356 2.3976 -0.5056 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7709 1.8035 -2.7096 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2887 0.8085 -2.3404 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1664 -0.5569 -2.2801 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5642 -1.1514 -0.4226 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5690 2.0495 0.7283 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0250 -2.4024 -0.8286 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0065 -3.8789 -1.5752 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3308 -3.8736 -0.3154 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6186 -3.2698 -2.0359 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9505 -0.6656 -0.7271 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7021 1.5843 -1.7448 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1731 1.6551 -0.7143 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5067 2.3438 2.1077 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6985 4.2532 3.0049 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0164 4.7622 2.1569 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0348 3.3378 0.4009 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0222 -2.8613 0.7324 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7701 -3.0029 -1.1090 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7836 -3.5612 -0.1671 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8212 0.8640 1.3807 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1875 -2.0978 0.7596 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2233 -0.1332 -0.1520 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3344 -1.6606 -1.7730 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4206 -1.4439 1.5702 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2060 0.1019 2.6669 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 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 10 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 15 24 1 0 24 25 1 0 5 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 26 31 1 0 28 3 1 0 12 7 1 0 23 18 1 0 19 9 1 0 1 32 1 0 2 33 1 0 2 34 1 0 3 35 1 6 5 36 1 6 8 37 1 0 11 38 1 0 14 39 1 0 14 40 1 0 14 41 1 0 16 42 1 0 17 43 1 0 17 44 1 0 20 45 1 0 21 46 1 0 22 47 1 0 23 48 1 0 24 49 1 0 24 50 1 0 25 51 1 0 26 52 1 1 27 53 1 6 28 54 1 1 29 55 1 0 30 56 1 0 31 57 1 0 M END

Standard InCHIKey	SABDCGUULUIQAJ-XNBWIAOKSA-N
Standard InCHI	InChI=1S/C23H26O8/c1-29-17-8-15-13(10-24)7-6-12-4-2-3-5-14(12)16(15)9-18(17)30-23-22(28)21(27)20(26)19(11-25)31-23/h2-5,7-9,19-28H,6,10-11H2,1H3/t19-,20-,21+,22-,23-/m1/s1
SMILES	OC[C@H]1O[C@@H](Oc2cc3c(cc2OC)C(=CCc2c3cccc2)CO)[C@@H]([C@H]([C@@H]1O)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
NPO9305	Iotrochota purpurea	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924179]
NPO8035	Tylophora tanakae	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350151]
NPO10900	Cinnamomum subavenium	Species	Lauraceae	Eukaryota	stems	Wulai Hsiang, Taipei County, Taiwan	2005-MAY	PMID[17253858]
NPO2298	Streptomyces platensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19581087]
NPO2298	Streptomyces platensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20299229]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[20363129]
NPO2298	Streptomyces platensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21214253]
NPO10900	Cinnamomum subavenium	Species	Lauraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23025417]
NPO9305	Iotrochota purpurea	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23131412]
NPO10900	Cinnamomum subavenium	Species	Lauraceae	Eukaryota	stem bark	Laifeng, Hubei Province, China	2012-JUL	PMID[26087384]
NPO11699	Ecballium elaterium	Species	Cucurbitaceae	Eukaryota	Fruit juice	n.a.	n.a.	PMID[3404148]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11699	Ecballium elaterium	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3378	Alstonia undulifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2298	Streptomyces platensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10737	Asteriscus aquaticus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11811	Capparis ovata	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12669	Cassine papillosa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9509	Charpentiera obovata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10900	Cinnamomum subavenium	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15252	Clathria prolifera	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6253	Conus pulicarius	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1182	Croton montevidensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12188	Datisca glomerata	Species	Datiscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12888	Echinus microtuberculatus	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10393	Ophidiaster ophidianus	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7045	Viviparus japonicus	Species	Viviparidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8035	Tylophora tanakae	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7709	Spiracantha cornifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2608	Solanum andigena	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3736	Scrophularia koelzii	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12436	Quercus imbricaria	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11256	Pseudowintera colorata	Species	Winteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4493	Polygonum flaccidum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20291	Phyllanthus oligospermus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11553	Phebalium dentatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12544	Dioscorea olfersiana	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8477	Myristica cagayanensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9922	Myelobia smerintha	Species	Crambidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12308	Metridium senile	Species	Metridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9672	Lotus ucrainicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5384	Ligustrum obtusifolium	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9305	Iotrochota purpurea	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5008	Hubertia tomentosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5823	Helichrysum auriceps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO761	Fagus fusca	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11699	Ecballium elaterium	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11699	Ecballium elaterium	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12308	Metridium senile	Species	Metridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8477	Myristica cagayanensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1182	Croton montevidensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11811	Capparis ovata	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4493	Polygonum flaccidum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10393	Ophidiaster ophidianus	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2608	Solanum andigena	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9672	Lotus ucrainicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7709	Spiracantha cornifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9922	Myelobia smerintha	Species	Crambidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5823	Helichrysum auriceps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9305	Iotrochota purpurea	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12544	Dioscorea olfersiana	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11699	Ecballium elaterium	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12436	Quercus imbricaria	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO761	Fagus fusca	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8035	Tylophora tanakae	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5008	Hubertia tomentosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20291	Phyllanthus oligospermus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2298	Streptomyces platensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12669	Cassine papillosa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12888	Echinus microtuberculatus	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3378	Alstonia undulifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15252	Clathria prolifera	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9509	Charpentiera obovata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6253	Conus pulicarius	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7045	Viviparus japonicus	Species	Viviparidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12188	Datisca glomerata	Species	Datiscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3736	Scrophularia koelzii	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11553	Phebalium dentatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10900	Cinnamomum subavenium	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10737	Asteriscus aquaticus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11256	Pseudowintera colorata	Species	Winteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5384	Ligustrum obtusifolium	Species	Oleaceae	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
Others	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
NPT2	Others	Unspecified	n.a.	IC50	=	50700.0	nM	PMID[23025417]

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 NPC60249 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	18710
0.1-0.2	28258
0.2-0.3	2273
0.3-0.4	530
0.4-0.5	83
0.5-0.6	3
0.6-0.7	1
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
0.6494	Remote Similarity	NPC76871
0.5422	Remote Similarity	NPC48309
0.5352	Remote Similarity	NPC270849
0.5057	Remote Similarity	NPC475754

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC60249 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4317
0.1-0.2	4759
0.2-0.3	66
0.3-0.4	7
0.4-0.5	1
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