NPASS Compound

Natural Product: NPC478338

Natural Product ID	NPC478338
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GECQUXSRPGFMCF-XVJIWKHGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 130143 0 0 0 0 0 0 0 0999 V2000 3.5218 2.7555 -0.1317 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4546 3.6603 -0.1729 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3155 4.5492 0.8624 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2256 4.5344 1.9191 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2691 3.6451 1.9536 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4137 2.7415 0.9050 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5253 1.7604 0.8960 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6502 2.1683 0.0093 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3628 2.0769 -1.4547 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9326 0.6471 -1.6921 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1842 0.0379 -2.8950 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7934 -1.2643 -3.0787 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1502 -1.9867 -2.0849 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8872 -1.3960 -0.8713 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2291 -2.1694 0.1805 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7661 -2.3501 0.0703 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2735 -3.4648 -0.6240 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9043 -3.6753 -0.7116 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0035 -2.8271 -0.1384 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4605 -1.7182 0.5542 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5031 -0.8027 1.2418 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4412 -0.1348 0.3248 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9041 0.7027 -0.6348 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7571 1.3514 -1.5181 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1191 1.1929 -1.4753 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6447 0.3525 -0.5092 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0861 0.1443 -0.4171 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6675 0.9349 0.6849 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1026 0.3993 1.8606 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6379 1.2270 2.8568 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7247 2.5802 2.6470 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2805 3.1099 1.4460 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7589 2.3078 0.4732 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3036 2.7932 -0.7524 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3605 2.0242 -1.9568 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0070 2.7033 -3.0546 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6434 3.9759 -3.4320 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2504 4.6277 -4.4871 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2486 3.9966 -5.1882 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6375 2.7324 -4.8422 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0078 2.1018 -3.7759 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6435 2.0966 -5.5489 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9075 4.6083 -6.2753 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8485 0.6442 -1.6644 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1902 0.6062 -1.2427 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9805 1.8305 -2.3521 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2473 3.4502 3.6054 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0714 -0.9443 2.1824 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8140 -0.3071 0.3828 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2597 -1.1568 1.3621 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5730 -1.4893 2.5379 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0292 -0.6403 3.6889 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3549 -1.1648 4.9196 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7617 -0.3505 5.9528 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8626 1.0274 5.8053 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5342 1.5564 4.5639 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1314 0.7262 3.5492 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6392 2.9420 4.4337 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2692 1.8551 6.8335 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0985 -1.5065 2.4028 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5651 -1.0567 3.6342 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4647 0.9265 -0.7562 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8252 -1.5209 0.6319 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2631 -0.3919 1.3375 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3721 -3.0306 -0.2198 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1045 -4.3850 -1.2350 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4886 -4.1830 -1.1998 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2449 -5.4494 -1.3870 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7890 -6.6461 -0.8986 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5069 -7.8187 -1.0887 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7146 -7.8023 -1.7866 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1709 -6.6006 -2.2756 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4327 -5.4330 -2.0719 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3734 -6.5752 -2.9728 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4283 -8.9991 -1.9723 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8692 -3.5700 0.1192 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3306 -4.3306 1.1431 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7697 -3.3234 -2.3147 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2917 -0.0602 -0.6925 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0232 0.5165 0.5255 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8225 0.7415 -3.8930 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1875 3.4164 0.3869 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0782 5.4428 2.9739 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2822 5.4901 0.9086 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5589 2.0902 -0.9836 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7377 3.6839 -0.9920 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9944 3.6164 2.7701 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9715 1.6726 1.9376 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4955 1.4462 0.2111 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6653 2.8054 -1.8588 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3487 2.2337 -1.9857 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9718 -1.8008 -4.0249 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4756 -1.7624 1.2053 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5118 -4.5290 -1.2421 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1361 0.0318 1.6624 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3526 2.0140 -2.2796 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3401 -0.9327 -0.3241 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9934 0.8116 3.8121 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3369 4.1897 1.2466 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8622 4.4995 -2.9003 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9757 5.6270 -4.7949 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3157 1.1270 -3.5156 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7253 1.1031 -5.6986 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9283 4.5522 -6.2278 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7226 -0.0370 -2.5114 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3655 -0.1235 -0.6120 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2720 3.4942 3.7328 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6186 -1.5685 1.5919 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9579 -2.5214 2.8131 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2948 -2.2278 5.0906 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0241 -0.7268 6.9327 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8781 1.1499 2.5877 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7298 3.4145 4.3027 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9992 2.8398 6.7720 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7766 -2.5930 2.3698 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1457 -0.3952 3.5267 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9040 1.2159 -1.6053 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6126 -0.4637 2.2786 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8599 -2.6874 -1.0331 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8457 -6.6190 -0.3616 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1531 -8.7516 -0.7077 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8120 -4.4943 -2.4705 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2567 -6.8794 -2.5881 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0716 -9.6416 -2.6811 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9465 -3.4709 0.2731 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5961 -3.8606 1.6089 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7724 1.0464 -3.8695 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8525 3.3450 1.0927 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4206 6.3988 2.9157 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5348 6.4918 0.8934 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 1 0 35 36 1 6 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 40 42 1 0 39 43 1 0 35 44 1 0 44 45 1 0 35 46 1 0 31 47 1 0 29 48 1 0 26 49 2 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 2 0 53 54 1 0 54 55 2 0 55 56 1 0 56 57 2 0 56 58 1 0 55 59 1 0 51 60 1 0 60 61 1 0 23 62 1 0 20 63 2 0 63 64 1 0 19 65 1 0 17 66 1 0 66 67 1 0 67 68 1 6 68 69 2 0 69 70 1 0 70 71 2 0 71 72 1 0 72 73 2 0 72 74 1 0 71 75 1 0 67 76 1 0 76 77 1 0 67 78 1 0 14 79 2 0 79 80 1 0 11 81 1 0 8 82 1 0 4 83 1 0 3 84 1 0 6 1 1 0 80 7 1 0 79 10 1 0 78 13 1 0 76 15 1 0 63 16 1 0 73 68 1 0 60 21 1 0 49 22 1 0 57 52 1 0 46 25 1 0 44 27 1 0 33 28 1 0 41 36 1 0 1 85 1 0 2 86 1 0 5 87 1 0 7 88 1 1 8 89 1 6 9 90 1 0 9 91 1 0 12 92 1 0 15 93 1 1 18 94 1 0 21 95 1 1 24 96 1 0 27 97 1 1 30 98 1 0 32 99 1 0 37100 1 0 38101 1 0 41102 1 0 42103 1 0 43104 1 0 44105 1 6 45106 1 0 47107 1 0 48108 1 0 51109 1 1 53110 1 0 54111 1 0 57112 1 0 58113 1 0 59114 1 0 60115 1 6 61116 1 0 62117 1 0 64118 1 0 65119 1 0 69120 1 0 70121 1 0 73122 1 0 74123 1 0 75124 1 0 76125 1 1 77126 1 0 81127 1 0 82128 1 0 83129 1 0 84130 1 0 M END

Standard InCHIKey	GECQUXSRPGFMCF-XVJIWKHGSA-N
Standard InCHI	InChI=1S/C60H46O24/c61-23-13-34(71)42-38(14-23)81-59(21-3-7-27(64)32(69)11-21)57(77)49(42)47-41(84-59)18-36(73)44-48(52(76)54(80-56(44)47)20-2-6-26(63)31(68)10-20)43-35(72)17-39-45(51(43)75)50-46-40(83-60(82-39,58(50)78)22-4-8-28(65)33(70)12-22)16-29(66)24-15-37(74)53(79-55(24)46)19-1-5-25(62)30(67)9-19/h1-14,16-18,37,48-50,52-54,57-58,61-78H,15H2/t37-,48+,49-,50-,52-,53-,54-,57-,58-,59+,60+/m1/s1
SMILES	c1cc(c(cc1[C@@H]1[C@@H](Cc2c(cc3c([C@H]4c5c(cc(c([C@H]6c7c(cc8c([C@H]9c%10c(cc(cc%10O[C@](c%10ccc(c(c%10)O)O)([C@@H]9O)O8)O)O)c7O[C@H](c7ccc(c(c7)O)O)[C@@H]6O)O)c5O)O)O[C@](c5ccc(c(c5)O)O)([C@@H]4O)O3)c2O1)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
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	2007; 2008	DOI[10.1007/s11746-010-1589-7]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	cotyledon	n.a.	PMID[11283027]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	seed	n.a.	PMID[12670184]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	seed	n.a.	PMID[21348467]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22537213]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Peanut Skins	n.a.	n.a.	PMID[28231711]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[36431807]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Leaf	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.		Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Seed	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Oil	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Oils	n.a.		Database[Phenol-Explorer]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Seeds	n.a.		Database[Phenol-Explorer]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	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	3

Activity Type	# Activity
Cell line	3

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	=	100.0	%	PMID[28231711]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	82.25	%	PMID[28231711]

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 NPC478338 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	27955
0.1-0.2	20443
0.2-0.3	1276
0.3-0.4	94
0.4-0.5	28
0.5-0.6	20
0.6-0.7	17
0.7-0.8	0
0.8-0.85	9
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC478337
0.9342	High Similarity	NPC78074
0.9114	High Similarity	NPC159526
0.8846	High Similarity	NPC478340
0.8462	Intermediate Similarity	NPC147743
0.8462	Intermediate Similarity	NPC4809
0.8462	Intermediate Similarity	NPC73517
0.8421	Intermediate Similarity	NPC478616
0.8421	Intermediate Similarity	NPC478339
0.8378	Intermediate Similarity	NPC272552
0.8378	Intermediate Similarity	NPC226108
0.8378	Intermediate Similarity	NPC322899
0.8025	Intermediate Similarity	NPC86630
0.7792	Intermediate Similarity	NPC46283
0.7792	Intermediate Similarity	NPC469944
0.7792	Intermediate Similarity	NPC134911
0.775	Intermediate Similarity	NPC471404
0.7692	Intermediate Similarity	NPC44192
0.7586	Intermediate Similarity	NPC478617
0.75	Intermediate Similarity	NPC106601
0.75	Intermediate Similarity	NPC151474
0.7412	Intermediate Similarity	NPC212614
0.7412	Intermediate Similarity	NPC205613
0.7051	Intermediate Similarity	NPC155564
0.6667	Remote Similarity	NPC226809
0.6456	Remote Similarity	NPC294558
0.6456	Remote Similarity	NPC18185
0.6456	Remote Similarity	NPC263940
0.6329	Remote Similarity	NPC58190
0.6329	Remote Similarity	NPC108811
0.6329	Remote Similarity	NPC170103
0.6329	Remote Similarity	NPC236202
0.6329	Remote Similarity	NPC262911
0.6329	Remote Similarity	NPC202742
0.625	Remote Similarity	NPC246202
0.625	Remote Similarity	NPC224161
0.625	Remote Similarity	NPC46335
0.625	Remote Similarity	NPC279406
0.625	Remote Similarity	NPC486519
0.6237	Remote Similarity	NPC484331
0.617	Remote Similarity	NPC12326
0.5773	Remote Similarity	NPC484330
0.5747	Remote Similarity	NPC278548
0.5618	Remote Similarity	NPC20050
0.5556	Remote Similarity	NPC185231
0.5529	Remote Similarity	NPC313116
0.5529	Remote Similarity	NPC603340
0.5402	Remote Similarity	NPC70409
0.5402	Remote Similarity	NPC204770
0.5402	Remote Similarity	NPC600551
0.5402	Remote Similarity	NPC601980
0.5402	Remote Similarity	NPC602065
0.5402	Remote Similarity	NPC611024
0.5385	Remote Similarity	NPC306267
0.5316	Remote Similarity	NPC178054
0.5301	Remote Similarity	NPC96576
0.5281	Remote Similarity	NPC600630
0.5281	Remote Similarity	NPC607896
0.5281	Remote Similarity	NPC611369
0.5176	Remote Similarity	NPC82917
0.5158	Remote Similarity	NPC9309

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC478338 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5745
0.1-0.2	3389
0.2-0.3	13
0.3-0.4	1
0.4-0.5	2
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