NPASS Compound

Natural Product: NPC478329

Natural Product ID	NPC478329
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CBCXLNKZLIRNPI-KIAQJTORSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10652866
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 106111 0 0 0 0 0 0 0 0999 V2000 8.3171 0.3838 2.9298 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1085 -0.4978 2.8084 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5571 -0.7556 1.6350 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1962 -0.1293 0.4586 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3986 -1.6011 1.5100 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7497 -1.9494 0.5058 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7777 -1.7431 -0.8757 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5933 -2.7379 -1.6218 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4306 -2.3103 -2.6229 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2177 -3.1713 -3.3578 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1472 -4.5214 -3.0592 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3127 -4.9477 -2.0616 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5249 -4.0756 -1.3276 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3518 -1.6992 -1.4837 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7330 -0.4663 -1.0191 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3608 0.6360 -1.1838 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4960 -0.3463 -0.3960 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9792 0.9349 0.0250 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3577 1.0841 -0.7239 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3425 2.0560 -0.2130 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7655 1.5793 0.0145 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9666 0.2109 0.5413 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5630 0.0657 1.9367 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6681 1.0010 2.2525 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1312 -1.3316 2.1365 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2857 -1.4622 1.2095 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8190 -1.3583 -0.1746 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4032 -0.8863 -0.3736 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0252 -0.5708 -1.6555 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1938 -0.2180 -0.9276 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5228 -1.9631 -0.4068 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5093 -3.1358 -1.0653 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4510 -3.3974 -1.8350 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3710 -4.1260 -0.8784 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2173 -2.3370 2.0813 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4781 0.1422 2.9936 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6843 -0.1793 4.1242 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0628 0.5949 2.8212 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2199 0.2254 3.6271 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4161 1.4374 1.8274 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7227 0.7667 1.4956 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3824 0.0341 2.5194 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7398 2.6659 1.1021 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4329 3.5330 0.8201 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7344 3.5304 1.8256 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6994 1.9881 -0.9215 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6777 2.9113 -0.8890 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7065 3.4703 0.2030 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6016 3.2507 -1.9506 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5433 4.2355 -1.7283 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4548 4.6020 -2.7051 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4489 3.9807 -3.9550 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5124 3.0010 -4.1765 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6184 2.6585 -3.1852 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3441 3.2114 -0.9868 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 -2.8545 -1.2731 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9259 -2.1218 2.7670 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1423 1.3805 2.4724 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5228 0.5828 3.9987 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2094 -0.0567 2.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6933 -0.9252 3.7264 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6311 0.7225 0.0395 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1968 0.3248 0.7349 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3833 -0.8819 -0.3146 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1681 -0.7187 -1.1036 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5176 -1.2455 -2.8931 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8848 -2.8250 -4.1564 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7515 -5.2261 -3.6165 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2378 -6.0048 -1.8056 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8703 -4.4676 -0.5360 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5485 -1.5689 -2.5893 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7295 1.6460 -0.2424 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0074 1.4223 -1.7511 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7705 0.0705 -0.9418 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0705 2.2433 0.8770 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8840 -0.1143 0.7543 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4024 1.1193 1.4291 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3605 2.0213 2.5281 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2248 0.6419 3.1741 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5455 -1.3181 3.1725 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7086 -2.4985 1.3827 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1029 -0.7856 1.4439 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0771 -2.2339 -0.7962 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3164 -1.4529 -2.2442 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6147 0.1739 -2.3222 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2313 -4.2263 0.2268 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4445 -3.7709 -1.3262 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7305 -5.1051 -1.2468 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2527 -2.9877 2.8197 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3646 -0.1705 1.9483 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9520 0.5691 3.3139 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2390 -1.0647 2.6425 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2880 4.6047 1.1987 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3076 3.2235 1.4323 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6517 3.7195 -0.2433 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1249 4.2792 2.4461 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3160 4.1828 1.1801 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2737 2.9949 2.6226 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5994 4.7569 -0.7768 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1976 5.3660 -2.5566 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1686 4.2738 -4.7172 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5197 2.5190 -5.1657 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9013 1.8847 -3.4030 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0782 3.0087 -1.9375 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 -2.6549 -1.2411 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1172 -2.7250 2.7682 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 1 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 6 31 32 1 0 32 33 2 0 32 34 1 0 25 35 1 0 23 36 1 0 36 37 2 0 36 38 1 0 38 39 2 0 38 40 1 0 40 41 2 0 41 42 1 0 40 43 1 0 43 44 1 0 43 45 1 0 21 46 1 0 46 47 1 0 47 48 2 0 47 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 52 53 1 0 53 54 2 0 20 55 1 6 14 56 1 0 5 57 1 0 13 8 1 0 41 18 1 0 54 49 1 0 43 20 1 0 28 22 1 0 30 27 1 0 1 58 1 0 1 59 1 0 1 60 1 0 2 61 1 0 4 62 1 0 4 63 1 0 4 64 1 0 7 65 1 1 9 66 1 0 10 67 1 0 11 68 1 0 12 69 1 0 13 70 1 0 14 71 1 6 18 72 1 1 19 73 1 0 19 74 1 0 21 75 1 1 22 76 1 1 24 77 1 0 24 78 1 0 24 79 1 0 25 80 1 1 26 81 1 0 26 82 1 0 27 83 1 6 29 84 1 0 29 85 1 0 34 86 1 0 34 87 1 0 34 88 1 0 35 89 1 0 42 90 1 0 42 91 1 0 42 92 1 0 44 93 1 0 44 94 1 0 44 95 1 0 45 96 1 0 45 97 1 0 45 98 1 0 50 99 1 0 51100 1 0 52101 1 0 53102 1 0 54103 1 0 55104 1 0 56105 1 0 57106 1 0 M END

Standard InCHIKey	CBCXLNKZLIRNPI-KIAQJTORSA-N
Standard InCHI	InChI=1S/C43H49NO13/c1-8-22(2)37(50)44-31(25-15-11-9-12-16-25)33(48)39(52)55-27-20-43(53)36(56-38(51)26-17-13-10-14-18-26)34-41(7,35(49)32(47)30(23(27)3)40(43,5)6)28(46)19-29-42(34,21-54-29)57-24(4)45/h8-18,27-29,31,33-34,36,46,48,53H,19-21H2,1-7H3,(H,44,50)/b22-8+/t27-,28+,29+,31-,33+,34-,36-,41+,42-,43+/m0/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(=O)C(=O)C(=C1C)C2(C)C)OC(=O)c1ccccc1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	787.32	Volume:	789.304 ? Van der Waals volume.
Dense:	0.997	LogP:	2.163 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.599 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.507 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	39.0
TPSA:	215.55 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.094	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.209	Fsp³:	0.488
MCE-18:	162.0 ? 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:	0.873	Fluc inhibitor:	0.129 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.079 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.356 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.005	Promiscuous compounds:	0.112

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.539	MDCK Permeability:	-5.021
Pgp-inhibitor:	0.944	Pgp-substrate:	0.984
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):	0.015
20% Bioavailability (F20%):	0.914	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.983
Plasma Protein Binding (PPB):	95.547%	Volume Distribution (VD):	0.353
Fu:	3.372% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.0
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.065
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.258
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.865 ? 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):

3.207

Half-life (T1/2):

2.954

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.034
Human Hepatotoxicity (H-HT):	0.997	Drug-induced Liver Injury (DILI):	0.991
AMES Toxicity:	0.958	Rat Oral Acute Toxicity:	0.43
Maximum Recommended Daily Dose:	0.924	Skin Sensitization:	1.0
Carcinogencity:	0.85	Eye Corrosion:	0.0
Eye Irritation:	0.01	Respiratory Toxicity:	0.067
Drug-induced Neurotoxicity:	0.657	Ototoxicity:	0.837
Hematotoxicity:	0.774	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.16
A549 Cytotoxicity:	0.285	Hek293 Cytotoxicity:	0.663
BCF:	0.484 ? 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:	3.282 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.047 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.167 ? 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
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0168-9452(00)00306-X]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np990201k]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	Needles	n.a.	n.a.	PMID[11325226]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13290	Taxus canadensis	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
Cell line	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
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	80.0	nM	PMID[11325226]

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 NPC478329 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	9614
0.1-0.2	37711
0.2-0.3	2411
0.3-0.4	56
0.4-0.5	12
0.5-0.6	19
0.6-0.7	11
0.7-0.8	2
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8367	Intermediate Similarity	NPC453583
0.8367	Intermediate Similarity	NPC191193
0.8283	Intermediate Similarity	NPC33372
0.8283	Intermediate Similarity	NPC67246
0.7573	Intermediate Similarity	NPC479183
0.7573	Intermediate Similarity	NPC479181
0.75	Intermediate Similarity	NPC487360
0.75	Intermediate Similarity	NPC479182
0.75	Intermediate Similarity	NPC479180
0.7455	Intermediate Similarity	NPC479173
0.7404	Intermediate Similarity	NPC471754
0.7404	Intermediate Similarity	NPC324251
0.7404	Intermediate Similarity	NPC206211
0.7333	Intermediate Similarity	NPC471629
0.7333	Intermediate Similarity	NPC306001
0.7222	Intermediate Similarity	NPC487361
0.7196	Intermediate Similarity	NPC275170
0.713	Intermediate Similarity	NPC486061
0.713	Intermediate Similarity	NPC486060
0.7048	Intermediate Similarity	NPC321072
0.7048	Intermediate Similarity	NPC215892
0.7048	Intermediate Similarity	NPC242662
0.7048	Intermediate Similarity	NPC102167
0.7048	Intermediate Similarity	NPC488127
0.6981	Remote Similarity	NPC471623
0.6981	Remote Similarity	NPC208553
0.6981	Remote Similarity	NPC181964
0.6981	Remote Similarity	NPC307628
0.6422	Remote Similarity	NPC327699
0.641	Remote Similarity	NPC472391
0.633	Remote Similarity	NPC473300
0.6224	Remote Similarity	NPC197037
0.6071	Remote Similarity	NPC317882
0.6071	Remote Similarity	NPC453588
0.6061	Remote Similarity	NPC91730
0.5982	Remote Similarity	NPC478328
0.5929	Remote Similarity	NPC473400
0.5902	Remote Similarity	NPC472375
0.5888	Remote Similarity	NPC603140
0.5868	Remote Similarity	NPC479186
0.5854	Remote Similarity	NPC479184
0.582	Remote Similarity	NPC479185
0.5752	Remote Similarity	NPC36607
0.5652	Remote Similarity	NPC603171
0.5534	Remote Similarity	NPC605573
0.5492	Remote Similarity	NPC289383
0.5447	Remote Similarity	NPC116862
0.5333	Remote Similarity	NPC155329
0.5333	Remote Similarity	NPC471606
0.5333	Remote Similarity	NPC114357
0.5288	Remote Similarity	NPC229545
0.5288	Remote Similarity	NPC248265
0.5288	Remote Similarity	NPC134685
0.5169	Remote Similarity	NPC473490

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC478329 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3113
0.1-0.2	5836
0.2-0.3	188
0.3-0.4	0
0.4-0.5	5
0.5-0.6	3
0.6-0.7	3
0.7-0.8	2
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
0.7048	Intermediate Similarity	NPD8360	Approved
0.7048	Intermediate Similarity	NPD8361	Phase 4
0.6981	Remote Similarity	NPD8485	Phase 4
0.6283	Remote Similarity	NPD8486	Phase 1
0.6273	Remote Similarity	NPD8424	Phase 3
0.5929	Remote Similarity	NPD8435	Phase 4
0.5433	Remote Similarity	NPD8462	Phase 2
0.5339	Remote Similarity	NPD8368	Phase 2

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