NPASS Compound

Natural Product: NPC36607

Natural Product ID	NPC36607
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LJTMOSWWGSCCPR-AMMYIWEDSA-N
IUPAC Name	n.a.
Synonyms	N-Methyltaxol C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL290758
PubChem CID	10260022
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

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 121126 0 0 0 0 0 0 0 0999 V2000 10.8895 2.6406 1.5063 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3668 2.2758 0.1579 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0577 1.5224 0.1868 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9835 2.3253 0.8476 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6435 1.5915 0.8698 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1446 1.3275 -0.4839 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7986 1.9153 -1.4244 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0643 0.5332 -0.8765 N 0 0 0 0 0 0 0 0 0 0 0 0 4.1498 -0.2360 -0.1040 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2710 0.5730 0.8162 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1677 -0.3794 1.2693 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3064 -1.2864 2.0938 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8894 -0.2353 0.7161 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2016 -1.1097 1.0917 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3773 -0.2548 1.4176 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7494 -0.8499 1.2433 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1948 -1.0393 2.5629 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7408 0.0416 0.6181 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1600 1.3629 0.9323 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4769 2.2122 1.8901 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3754 1.9250 2.6906 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8471 3.5231 2.1191 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2190 4.3196 3.1666 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6639 5.5640 3.3953 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6949 6.0497 2.5519 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3082 5.2613 1.4928 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8714 4.0013 1.2634 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2997 0.1617 -0.6818 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1342 -0.5073 -1.9521 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7973 -1.0311 -2.3343 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2122 -0.4068 -3.1785 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9046 -2.2125 -1.9317 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8176 -2.1727 -0.4444 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5653 -1.8585 -0.1868 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5309 -2.1912 -1.1155 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6788 -2.2987 0.7565 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9688 -3.1659 1.8151 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0027 -2.9142 0.5930 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3848 -3.4151 -2.4602 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8229 -4.2109 -3.4043 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7389 -3.8726 -3.8992 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -5.4647 -3.8049 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0584 -1.6344 -2.3516 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4332 0.6090 -3.0111 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6627 -0.0365 -4.2155 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2716 1.7139 -2.6372 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9431 1.8085 -1.2985 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8139 0.4907 -0.5193 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8397 0.1977 -1.4697 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2989 1.5499 -1.3320 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2096 0.5253 0.7708 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3656 0.6937 1.4383 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3569 0.8604 0.6954 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5005 0.6888 2.9230 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6284 1.5632 0.0320 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8170 -1.3598 0.5695 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0424 -1.4437 1.9094 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6471 -2.5654 2.4933 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0383 -3.6330 1.7142 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8212 -3.5659 0.3685 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2258 -2.4602 -0.1981 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8298 0.4843 -2.3493 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9646 2.3632 1.5627 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8817 3.7530 1.6721 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3591 2.1292 2.3185 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2963 3.2200 -0.4527 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1536 1.6632 -0.3702 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2580 0.5973 0.7814 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8336 1.1752 -0.8328 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8511 3.2977 0.3245 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2770 2.4840 1.9041 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7538 0.7046 1.5150 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9228 2.2757 1.3743 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4066 -0.7203 -0.8305 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8052 0.9170 1.6685 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2086 -1.7506 1.8432 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2517 0.6588 0.7491 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1731 0.0696 2.4875 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6942 -0.5324 3.2289 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5717 0.0415 1.3634 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9733 3.9957 3.8684 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9639 6.1803 4.2283 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 7.0305 2.6974 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5557 5.6334 0.8342 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5863 3.3752 0.4536 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8889 1.2283 -1.0030 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9433 -2.0654 -2.4400 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4436 -2.2906 -0.4447 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8287 -1.3753 -1.7982 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4833 -3.1974 -1.5585 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6147 -4.0370 2.1407 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0908 -3.6832 1.3832 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8075 -2.6186 2.7429 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9884 -3.5944 -0.2783 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1974 -3.6034 1.4566 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8451 -2.2144 0.4538 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9515 -6.0154 -4.5925 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8112 -6.0907 -2.9563 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4966 -5.1749 -4.3022 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5169 -2.6421 -2.3832 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8325 -1.9076 -1.6228 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4025 -1.5800 -3.4084 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3986 1.0704 -3.1837 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7853 0.6067 -4.9416 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7793 2.7359 -2.7444 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1012 1.8160 -3.4069 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6773 2.6273 -0.6372 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6801 -0.5137 -1.1670 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7623 0.1003 -2.5376 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5588 0.5724 3.4626 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9924 1.6235 3.2849 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2050 -0.1272 3.2440 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2080 2.3596 0.1089 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7803 -0.6243 2.5609 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8157 -2.6106 3.5606 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5074 -4.4861 2.2143 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1344 -4.4181 -0.2496 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0608 -2.4237 -1.2680 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1572 1.3410 -2.5642 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7816 0.6144 -2.8823 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3471 -0.4640 -2.6341 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 2 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 18 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 33 36 1 0 36 37 1 0 36 38 1 0 32 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 29 43 1 1 29 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 48 51 1 1 51 52 1 0 52 53 2 0 52 54 1 0 10 55 1 0 9 56 1 0 56 57 2 0 57 58 1 0 58 59 2 0 59 60 1 0 60 61 2 0 8 62 1 0 34 14 1 0 50 47 1 0 61 56 1 0 36 16 1 0 27 22 1 0 48 28 1 0 1 63 1 0 1 64 1 0 1 65 1 0 2 66 1 0 2 67 1 0 3 68 1 0 3 69 1 0 4 70 1 0 4 71 1 0 5 72 1 0 5 73 1 0 9 74 1 6 10 75 1 1 14 76 1 1 15 77 1 0 15 78 1 0 17 79 1 0 18 80 1 1 23 81 1 0 24 82 1 0 25 83 1 0 26 84 1 0 27 85 1 0 28 86 1 6 32 87 1 6 35 88 1 0 35 89 1 0 35 90 1 0 37 91 1 0 37 92 1 0 37 93 1 0 38 94 1 0 38 95 1 0 38 96 1 0 42 97 1 0 42 98 1 0 42 99 1 0 43100 1 0 43101 1 0 43102 1 0 44103 1 6 45104 1 0 46105 1 0 46106 1 0 47107 1 1 49108 1 0 49109 1 0 54110 1 0 54111 1 0 54112 1 0 55113 1 0 57114 1 0 58115 1 0 59116 1 0 60117 1 0 61118 1 0 62119 1 0 62120 1 0 62121 1 0 M END

Standard InCHIKey	LJTMOSWWGSCCPR-AMMYIWEDSA-N
Standard InCHI	InChI=1S/C47H59NO14/c1-9-10-13-22-34(52)48(8)36(29-18-14-11-15-19-29)37(53)43(56)60-31-24-47(57)41(61-42(55)30-20-16-12-17-21-30)39-45(7,32(51)23-33-46(39,25-58-33)62-28(4)50)40(54)38(59-27(3)49)35(26(31)2)44(47,5)6/h11-12,14-21,31-33,36-39,41,51,53,57H,9-10,13,22-25H2,1-8H3/t31-,32-,33+,36-,37+,38+,39-,41-,45+,46-,47+/m0/s1
SMILES	CCCCCC(=O)N([C@H]([C@H](C(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)[C@H]3[C@@](C(=O)[C@@H](C(=C1C)C2(C)C)OC(=O)C)(C)[C@@H](O)C[C@@H]1[C@]3(CO1)OC(=O)C)O)c1ccccc1)C

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
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542368]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23265441]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28139925]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184894]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561894]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7908950]
NPO33211	japanese yew	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9873389]
NPO33211	japanese yew	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23840	Taxus x media	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23840	Taxus x media	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23840	Taxus x media	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23840	Taxus x media	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23840	Taxus x media	Species	Taxaceae	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
ED50	1
Ratio ED50	1

Activity Type	# Activity
Cell line	1
Non-molecular	1
Others	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
NPT137	Cell line	L1210	Mus musculus	IC50	=	0.48	ug.mL-1	PMID[9873389]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	0.17	ug.mL-1	PMID[9873389]
NPT2	Others	Unspecified	n.a.	ED50	=	1.91	uM	PMID[7908950]
NPT2	Others	Unspecified	n.a.	Ratio ED50	=	1.66	n.a.	PMID[7908950]

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 NPC36607 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	11409
0.1-0.2	36312
0.2-0.3	1971
0.3-0.4	96
0.4-0.5	18
0.5-0.6	28
0.6-0.7	13
0.7-0.8	1
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
0.766	Intermediate Similarity	NPC603140
0.7115	Intermediate Similarity	NPC471629
0.7115	Intermediate Similarity	NPC306001
0.7087	Intermediate Similarity	NPC471623
0.7087	Intermediate Similarity	NPC208553
0.7087	Intermediate Similarity	NPC181964
0.7087	Intermediate Similarity	NPC307628
0.7019	Intermediate Similarity	NPC33372
0.7019	Intermediate Similarity	NPC67246
0.7019	Intermediate Similarity	NPC324251
0.7019	Intermediate Similarity	NPC206211
0.6952	Remote Similarity	NPC487360
0.6952	Remote Similarity	NPC479182
0.6952	Remote Similarity	NPC479180
0.6923	Remote Similarity	NPC473400
0.6923	Remote Similarity	NPC603171
0.6822	Remote Similarity	NPC275170
0.6759	Remote Similarity	NPC486061
0.6759	Remote Similarity	NPC486060
0.6697	Remote Similarity	NPC487361
0.6526	Remote Similarity	NPC155329
0.6526	Remote Similarity	NPC114357
0.6514	Remote Similarity	NPC471606
0.6082	Remote Similarity	NPC605573
0.5856	Remote Similarity	NPC453583
0.5856	Remote Similarity	NPC317882
0.5856	Remote Similarity	NPC453588
0.5804	Remote Similarity	NPC471754
0.5766	Remote Similarity	NPC321072
0.5766	Remote Similarity	NPC215892
0.5766	Remote Similarity	NPC242662
0.5766	Remote Similarity	NPC102167
0.5766	Remote Similarity	NPC488127
0.5752	Remote Similarity	NPC478329
0.5743	Remote Similarity	NPC259144
0.5743	Remote Similarity	NPC219419
0.5714	Remote Similarity	NPC191193
0.5676	Remote Similarity	NPC473300
0.5664	Remote Similarity	NPC479183
0.5664	Remote Similarity	NPC479181
0.5625	Remote Similarity	NPC327699
0.5403	Remote Similarity	NPC479184
0.5351	Remote Similarity	NPC473490
0.5347	Remote Similarity	NPC197037
0.5347	Remote Similarity	NPC229545
0.5347	Remote Similarity	NPC248265
0.5347	Remote Similarity	NPC134685
0.5246	Remote Similarity	NPC116862
0.5196	Remote Similarity	NPC91730
0.5161	Remote Similarity	NPC472391
0.5146	Remote Similarity	NPC217918
0.512	Remote Similarity	NPC479185

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC36607 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3542
0.1-0.2	5478
0.2-0.3	117
0.3-0.4	0
0.4-0.5	5
0.5-0.6	4
0.6-0.7	3
0.7-0.8	1
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
0.7087	Intermediate Similarity	NPD8485	Phase 4
0.6389	Remote Similarity	NPD8368	Phase 2
0.6364	Remote Similarity	NPD8486	Phase 1
0.6	Remote Similarity	NPD8462	Phase 2
0.5909	Remote Similarity	NPD8424	Phase 3
0.5766	Remote Similarity	NPD8360	Approved
0.5766	Remote Similarity	NPD8361	Phase 4
0.5439	Remote Similarity	NPD8435	Phase 4

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