NPASS Compound

Natural Product: NPC479173

Natural Product ID	NPC479173
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CPQYBXIJDMJNHB-MKQAHOERSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	132967476
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 123129 0 0 0 0 0 0 0 0999 V2000 -2.4605 -7.2358 1.4468 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4898 -6.2249 1.8258 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1462 -4.9424 1.9693 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7192 -4.6106 1.7309 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1346 -3.9554 2.3529 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8347 -2.7207 2.4949 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.7501 -1.6805 2.8744 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7882 -1.7086 4.3790 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6168 -1.7979 5.0917 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6093 -1.8219 6.4817 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8044 -1.7548 7.1567 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9905 -1.6654 6.4687 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9708 -1.6430 5.0697 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3656 -0.3250 2.4136 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2934 -0.0951 0.9766 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3535 -0.1599 0.3012 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1611 0.1937 0.2717 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1005 0.4400 -1.1473 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3378 1.7455 -1.3844 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2198 1.7907 -2.3109 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1965 1.9515 -1.9580 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0097 1.2225 -0.9893 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9863 0.1501 -1.5147 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8113 0.5130 -2.6626 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9120 -0.2993 -0.4040 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3767 0.1153 0.9795 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5418 1.5784 1.0234 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7220 2.1976 -0.0840 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9588 2.8623 -0.5018 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6849 1.9988 0.3451 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8029 3.1486 0.4485 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2464 2.8676 1.2721 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4335 1.6737 1.6009 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1400 3.9699 1.7602 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2199 0.0839 -0.5305 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1280 -0.9502 -0.3499 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0734 -1.2102 -1.4586 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7265 -2.5789 -1.2118 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2175 -2.6474 0.1895 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3250 -2.0179 1.2157 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8930 -0.7427 0.8113 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2997 -4.0226 0.5156 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8365 -2.5961 -2.0883 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4834 -1.3204 -2.7111 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2392 -1.1445 -1.8125 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8526 -2.1777 -1.9081 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2191 -1.3877 -2.0187 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6564 -2.5085 -1.8332 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2865 -0.4894 -2.4175 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2883 -0.7714 -1.5874 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4465 -2.1381 -1.1875 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4318 0.6216 -3.3608 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7770 0.7415 -3.9961 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3885 0.6083 -4.3988 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3542 3.3812 -1.6626 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9775 4.2426 -2.5044 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4521 3.7833 -3.5959 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1094 5.6491 -2.1875 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8166 6.4853 -3.0537 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9596 7.8286 -2.8015 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 8.3762 -1.6513 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6904 7.5685 -0.7963 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5695 6.2275 -1.0842 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4656 2.9050 -3.1794 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0879 -0.0599 2.9629 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4364 -4.3555 2.5717 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9241 -8.2516 1.5748 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1815 -7.1461 0.3701 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5767 -7.2282 2.0934 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5319 -6.5006 1.9933 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0170 -5.2762 2.2650 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5934 -3.5428 2.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4656 -4.6516 0.6534 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7526 -1.9508 2.4888 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6885 -1.8505 4.5624 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7031 -1.8903 7.0579 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8611 -1.7691 8.2482 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9396 -1.6116 6.9830 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8822 -1.5733 4.4930 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0204 0.4663 2.8829 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0983 0.4004 -1.5479 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2445 2.1929 -0.3970 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2077 2.3957 -1.8143 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7178 1.8931 -2.9821 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3500 0.6278 -0.3335 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8672 0.7876 -2.3583 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5176 1.2815 -3.3562 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9873 -0.4020 -3.3123 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9574 -1.4275 -0.2850 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0614 -0.3542 1.7140 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3911 -0.3033 1.1439 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4861 2.0829 2.0069 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2944 2.9025 -1.5247 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0982 3.9019 -0.0686 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6515 4.3663 0.8414 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5524 4.8125 2.1655 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9251 3.5933 2.4214 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5457 -1.8726 -0.1416 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9372 -0.4823 -1.4713 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0431 -3.3996 -1.4962 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2686 -2.2639 0.2790 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4257 -2.6894 1.3270 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8987 -1.9684 2.1605 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8217 -4.5135 -0.1546 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6890 -2.4426 -1.5847 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9021 -0.7107 -3.3867 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8125 -2.8954 -1.9134 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5179 -2.0341 -0.7670 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0964 -2.4974 -0.1948 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7097 0.8196 -5.1222 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3741 -0.2006 -3.8422 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3512 1.6413 -3.6988 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0610 1.5769 -4.8048 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8616 0.1031 -5.3043 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4527 -0.0965 -4.1656 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2445 6.0056 -3.9385 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5124 8.4602 -3.4839 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5204 9.4521 -1.4808 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2487 7.9780 0.0862 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0078 5.5592 -0.4126 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6226 2.6708 -4.0926 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1152 0.5081 3.7486 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0681 -3.8446 3.1807 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 3 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 7 14 1 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 1 0 18 19 1 0 19 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 0 29 30 1 0 28 31 1 1 31 32 1 0 32 33 2 0 32 34 1 0 25 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 37 44 1 0 23 45 1 0 45 46 2 0 45 47 1 0 47 48 2 0 47 49 1 0 49 50 2 0 50 51 1 0 49 52 1 0 52 53 1 0 52 54 1 0 21 55 1 0 55 56 1 0 56 57 2 0 56 58 1 0 58 59 2 0 59 60 1 0 60 61 2 0 61 62 1 0 62 63 2 0 20 64 1 6 14 65 1 0 5 66 1 0 13 8 1 0 50 18 1 0 63 58 1 0 52 20 1 0 28 22 1 0 41 36 1 0 30 27 1 0 1 67 1 0 1 68 1 0 1 69 1 0 2 70 1 0 4 71 1 0 4 72 1 0 4 73 1 0 7 74 1 6 9 75 1 0 10 76 1 0 11 77 1 0 12 78 1 0 13 79 1 0 14 80 1 1 18 81 1 6 19 82 1 0 19 83 1 0 21 84 1 6 22 85 1 1 24 86 1 0 24 87 1 0 24 88 1 0 25 89 1 1 26 90 1 0 26 91 1 0 27 92 1 1 29 93 1 0 29 94 1 0 34 95 1 0 34 96 1 0 34 97 1 0 36 98 1 1 37 99 1 6 38100 1 6 39101 1 6 40102 1 0 40103 1 0 42104 1 0 43105 1 0 44106 1 0 51107 1 0 51108 1 0 51109 1 0 53110 1 0 53111 1 0 53112 1 0 54113 1 0 54114 1 0 54115 1 0 59116 1 0 60117 1 0 61118 1 0 62119 1 0 63120 1 0 64121 1 0 65122 1 0 66123 1 0 M END

Standard InCHIKey	CPQYBXIJDMJNHB-MKQAHOERSA-N
Standard InCHI	InChI=1S/C48H57NO17/c1-8-23(2)41(57)49-33(26-15-11-9-12-16-26)36(54)43(59)63-29-20-48(60)40(65-42(58)27-17-13-10-14-18-27)38-46(7,39(56)35(53)32(24(29)3)45(48,5)6)30(19-31-47(38,22-62-31)66-25(4)50)64-44-37(55)34(52)28(51)21-61-44/h8-18,28-31,33-34,36-38,40,44,51-52,54-55,60H,19-22H2,1-7H3,(H,49,57)/b23-8+/t28-,29+,30+,31-,33+,34+,36-,37-,38+,40+,44+,46-,47+,48-/m1/s1
SMILES	C/C=C(C)/C(=N[C@@H](c1ccccc1)[C@H](C(=O)O[C@H]1C[C@]2([C@H]([C@H]3[C@@](C)([C@H](C[C@@H]4[C@]3(CO4)OC(=O)C)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O)C(=O)C(=O)C(=C1C)C2(C)C)OC(=O)c1ccccc1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	919.36	Volume:	902.389 ? Van der Waals volume.
Dense:	1.019	LogP:	1.578 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.204 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.971 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	45.0
TPSA:	274.47 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	6.0	Rings:	7.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.062	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.758	Fsp³:	0.542
MCE-18:	190.27 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	1
Colloidal aggregators:	0.995	Fluc inhibitor:	0.128 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.035 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.232 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.005	Promiscuous compounds:	0.086

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.653	MDCK Permeability:	-5.116
Pgp-inhibitor:	0.122	Pgp-substrate:	0.993
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.661	30% Bioavailability (F30%):	0.979
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.935
Plasma Protein Binding (PPB):	90.543%	Volume Distribution (VD):	-0.264
Fu:	8.807% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.0
BSEP inhibitor:	0.975

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.098
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.855 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

1.221

Half-life (T1/2):

3.05

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.014
Human Hepatotoxicity (H-HT):	0.995	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.98	Rat Oral Acute Toxicity:	0.08
Maximum Recommended Daily Dose:	0.689	Skin Sensitization:	1.0
Carcinogencity:	0.385	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.25	Ototoxicity:	0.964
Hematotoxicity:	0.86	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.178
A549 Cytotoxicity:	0.573	Hek293 Cytotoxicity:	0.694
BCF:	0.469 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.268 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.063 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.107 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	needles	Himalayan	n.a.	PMID[16480866]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Stem Bark	n.a.	n.a.	PMID[28240909]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28581744]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264680]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23720	Taxus wallichiana	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	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	=	142000.0	nM	PMID[28240909]

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 NPC479173 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	9919
0.1-0.2	36123
0.2-0.3	3717
0.3-0.4	41
0.4-0.5	17
0.5-0.6	27
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8532	High Similarity	NPC472391
0.7876	Intermediate Similarity	NPC479186
0.7807	Intermediate Similarity	NPC479185
0.7586	Intermediate Similarity	NPC472375
0.7521	Intermediate Similarity	NPC479184
0.7456	Intermediate Similarity	NPC289383
0.7455	Intermediate Similarity	NPC478329
0.7391	Intermediate Similarity	NPC116862
0.6667	Remote Similarity	NPC472392
0.6522	Remote Similarity	NPC453583
0.6466	Remote Similarity	NPC33372
0.6466	Remote Similarity	NPC67246
0.6379	Remote Similarity	NPC191193
0.6293	Remote Similarity	NPC478328
0.5917	Remote Similarity	NPC479183
0.5917	Remote Similarity	NPC479181
0.5868	Remote Similarity	NPC487360
0.5868	Remote Similarity	NPC479182
0.5868	Remote Similarity	NPC479180
0.5826	Remote Similarity	NPC471493
0.5785	Remote Similarity	NPC471754
0.5785	Remote Similarity	NPC324251
0.5785	Remote Similarity	NPC206211
0.5738	Remote Similarity	NPC471629
0.5738	Remote Similarity	NPC306001
0.568	Remote Similarity	NPC487361
0.5645	Remote Similarity	NPC275170
0.562	Remote Similarity	NPC321072
0.562	Remote Similarity	NPC215892
0.562	Remote Similarity	NPC242662
0.56	Remote Similarity	NPC486061
0.56	Remote Similarity	NPC486060
0.5574	Remote Similarity	NPC208553
0.5574	Remote Similarity	NPC181964
0.5574	Remote Similarity	NPC307628
0.5492	Remote Similarity	NPC327699
0.5492	Remote Similarity	NPC102167
0.5492	Remote Similarity	NPC488127
0.5447	Remote Similarity	NPC471623
0.5366	Remote Similarity	NPC473490
0.5128	Remote Similarity	NPC479175

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479173 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3423
0.1-0.2	5567
0.2-0.3	147
0.3-0.4	1
0.4-0.5	5
0.5-0.6	5
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	Drug ID	Developmental Stage
0.6102	Remote Similarity	NPD8435	Phase 4
0.562	Remote Similarity	NPD8424	Phase 3
0.5574	Remote Similarity	NPD8485	Phase 4
0.5492	Remote Similarity	NPD8360	Approved
0.5492	Remote Similarity	NPD8361	Phase 4
0.5039	Remote Similarity	NPD8486	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