NPASS Compound

Natural Product: NPC57954

Natural Product ID	NPC57954
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(1R,3As,5Ar,5Br,7Ar,8S,9R,11As,12R,13Ar)-9,12-Dihydroxy-5A,5B,8,11A-Tetramethyl-1-(Prop-1-En-2-Yl)Icosahydro-1H-Cyclopenta[A]Chrysene-3A,8-Dicarboxylic Acid
IUPAC Name	(1R,3aS,5aR,5bR,7aR,8S,9R,11aS,11bR,12R,13aR,13bR)-9,12-dihydroxy-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a,8-dicarboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3357707
PubChem CID	14866192
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 82 86 0 0 0 0 0 0 0 0999 V2000 -5.6357 2.5872 -0.8035 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5094 1.9884 -0.0501 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7938 2.7349 0.7420 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2475 0.5397 -0.2501 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4621 -0.2083 0.2576 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9334 -1.2200 1.2689 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5665 -1.4634 0.6807 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1073 -0.0341 0.4657 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7989 -0.1206 -0.2869 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2929 1.1655 -0.8182 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0755 0.9737 -1.4694 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5058 2.2305 -1.8858 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9906 0.4055 -0.4104 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5470 -0.9750 -0.0728 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8056 -0.7896 0.6439 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6756 0.0880 1.8514 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2556 -2.1318 1.0986 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6501 -2.1977 1.6336 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3756 -1.8786 -1.2628 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4860 -1.7034 0.8522 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8704 -1.6601 0.1881 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2673 -0.1979 0.2291 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4385 0.5801 -0.7283 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7677 0.3025 -2.1721 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7613 2.0652 -0.5000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9680 2.2326 0.3916 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1254 1.4011 -0.0931 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7437 -0.0508 0.0863 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3388 -0.8984 -0.9980 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3584 -0.4885 1.3770 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1722 -1.4455 1.4345 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0631 0.1385 2.5793 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2244 1.7389 0.7302 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7274 -2.2417 -0.5623 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1701 -3.3923 -0.6769 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4427 -1.8672 -1.6797 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3229 1.8512 -1.2292 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2585 3.2474 -0.1335 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2692 3.2183 -1.6621 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0551 3.8021 0.8246 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9582 2.4432 1.3519 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1507 0.3519 -1.3454 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0623 -0.6757 -0.5446 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0998 0.5251 0.8358 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8484 -0.7617 2.2737 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5711 -2.1091 1.2399 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9709 0.4159 1.4757 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0459 -0.7530 -1.1696 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1638 1.9907 -0.1260 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9756 1.5099 -1.6295 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0672 0.3539 -2.3473 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1685 2.4192 -2.8080 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7973 1.0370 0.5097 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3317 -0.2779 2.6988 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0016 1.1372 1.6995 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3260 0.1629 2.2904 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5842 -2.4582 1.9277 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1328 -2.9009 0.3074 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7574 -1.8738 2.6784 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9693 -3.2630 1.6004 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 -2.1506 -1.5237 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8447 -1.4559 -2.1991 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9090 -2.8711 -1.1537 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1995 -2.7942 0.8214 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6105 -1.3200 1.8450 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7243 -2.0033 -0.8503 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5855 -2.3087 0.7133 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9988 0.1568 1.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9005 0.6037 -2.8226 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5938 0.9979 -2.5058 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1171 -0.7070 -2.3752 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9238 2.5936 -0.0004 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9637 2.5952 -1.4331 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2784 3.2974 0.3050 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7755 2.0339 1.4465 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4342 1.6528 -1.1146 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4795 -0.3785 -1.9567 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7849 -1.8642 -1.0962 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3772 -1.2117 -0.6788 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5711 -0.0978 3.4245 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9193 2.1122 1.5918 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0517 -2.4801 -2.2074 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 14 19 1 6 14 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 28 30 1 0 30 31 2 0 30 32 1 0 27 33 1 0 7 34 1 6 34 35 2 0 34 36 1 0 8 4 1 0 15 9 1 0 28 22 1 0 18 7 1 0 23 13 1 0 1 37 1 0 1 38 1 0 1 39 1 0 3 40 1 0 3 41 1 0 4 42 1 6 5 43 1 0 5 44 1 0 6 45 1 0 6 46 1 0 8 47 1 1 9 48 1 6 10 49 1 0 10 50 1 0 11 51 1 6 12 52 1 0 13 53 1 1 16 54 1 0 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 18 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 19 63 1 0 20 64 1 0 20 65 1 0 21 66 1 0 21 67 1 0 22 68 1 1 24 69 1 0 24 70 1 0 24 71 1 0 25 72 1 0 25 73 1 0 26 74 1 0 26 75 1 0 27 76 1 6 29 77 1 0 29 78 1 0 29 79 1 0 32 80 1 0 33 81 1 0 36 82 1 0 M END

Standard InCHIKey	VZYJGZZXVOHUMY-DPPLFAKZSA-N
Standard InCHI	InChI=1S/C30H46O6/c1-16(2)17-7-12-30(25(35)36)14-13-27(4)18(22(17)30)15-19(31)23-26(3)10-9-21(32)29(6,24(33)34)20(26)8-11-28(23,27)5/h17-23,31-32H,1,7-15H2,2-6H3,(H,33,34)(H,35,36)/t17-,18+,19+,20+,21+,22+,23+,26-,27+,28+,29-,30-/m0/s1
SMILES	CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1C[C@@H](O)[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CC[C@H]([C@@]1(C)C(=O)O)O)C(=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
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)89267-5]
NPO6003	Halorosellinia oceanica	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11454459]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12882150]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15666542]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	stem	n.a.	PMID[16252920]
NPO12610	Diospyros dendo	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16441080]
NPO3029	Daedalea dickinsii	Species	Coriolaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[17986791]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	Turkey	n.a.	PMID[19299148]
NPO6003	Halorosellinia oceanica	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO6003	Halorosellinia oceanica	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21265556]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	trunk bark	n.a.	PMID[556731]
NPO13061	Balanocarpus zeylanicus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5200	Diphylleia grayi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3029	Daedalea dickinsii	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12781	Schefflera heptaphylla	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6003	Halorosellinia oceanica	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12610	Diospyros dendo	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10670	Bidens frondosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Tuber	n.a.	n.a.	Database[FooDB]
NPO22136	Hedysarum alpinum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Tubers	n.a.		Database[FooDB]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5200	Diphylleia grayi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5200	Diphylleia grayi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5200	Diphylleia grayi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12019	Orontium japonicum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5200	Diphylleia grayi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12781	Schefflera heptaphylla	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15495	Narcissus cantabricus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3568	Myristica dactyloides	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14426	Halictus sexcinctus	Species	Halictidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10670	Bidens frondosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15944	Primnoa resedaeformis	Species	Primnoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22136	Hedysarum alpinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12836	Mentha javanica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13061	Balanocarpus zeylanicus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1349	Zanthoxylum zanthoxyloides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6003	Halorosellinia oceanica	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12610	Diospyros dendo	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3029	Daedalea dickinsii	Species	Coriolaceae	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	2

Activity Type	# Activity
Cell line	2

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	>	255000.0	nM	PMID[25442310]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	255000.0	nM	PMID[25442310]

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 NPC57954 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	25945
0.1-0.2	21330
0.2-0.3	2283
0.3-0.4	222
0.4-0.5	53
0.5-0.6	17
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
0.7705	Intermediate Similarity	NPC213832
0.7188	Intermediate Similarity	NPC2783
0.7077	Intermediate Similarity	NPC269360
0.6866	Remote Similarity	NPC169933
0.5735	Remote Similarity	NPC264317
0.5735	Remote Similarity	NPC294438
0.5652	Remote Similarity	NPC488164
0.5652	Remote Similarity	NPC264005
0.5556	Remote Similarity	NPC88744
0.5556	Remote Similarity	NPC252714
0.5526	Remote Similarity	NPC253586
0.5429	Remote Similarity	NPC488506
0.5429	Remote Similarity	NPC291373
0.5429	Remote Similarity	NPC220498
0.5405	Remote Similarity	NPC606727
0.5362	Remote Similarity	NPC471900
0.5139	Remote Similarity	NPC277399
0.507	Remote Similarity	NPC80590
0.5068	Remote Similarity	NPC151191
0.5068	Remote Similarity	NPC16377
0.5067	Remote Similarity	NPC602147

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC57954 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6634
0.1-0.2	2461
0.2-0.3	44
0.3-0.4	9
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
0.5735	Remote Similarity	NPD7520	Phase 1

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