NPASS Compound

Natural Product: NPC14752

Natural Product ID	NPC14752
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	TYLVGQKNNUHXIP-DAYPOXPHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11970038
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 108114 0 0 0 0 0 0 0 0999 V2000 1.0396 0.0199 -2.7813 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2775 -0.3217 -1.5498 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4940 -1.3965 -1.5449 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0724 -1.5420 -2.9063 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5392 -1.5830 -2.7488 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0307 -2.4586 -3.4927 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7003 -0.9518 -2.0134 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6939 -2.0465 -1.8177 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2715 -0.0492 -3.0940 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4480 0.6471 -2.5838 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3773 1.1500 -1.2164 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0849 1.0257 -0.4771 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1367 1.0478 0.5996 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9194 0.2914 -0.2165 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2952 -0.2080 -0.7574 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8573 -1.0613 0.3733 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3591 -1.1239 0.6670 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6333 0.1416 0.7442 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3096 0.5428 -0.3399 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6220 0.8377 0.0801 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1923 2.0880 -0.0143 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4297 2.9758 -0.5296 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5423 2.4846 0.4066 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5940 1.6835 -0.3343 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5690 0.2610 0.0842 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2255 -0.7679 -0.7570 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2146 -2.0899 -0.3295 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5573 -2.3748 0.9723 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9072 -1.3630 1.8422 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9057 -0.0617 1.3780 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8903 2.2329 0.0890 N 0 0 0 0 0 0 0 0 0 0 0 0 6.9867 1.7980 -0.4226 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2456 2.3777 0.0329 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2646 3.3758 1.0001 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4462 3.9243 1.4263 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6681 3.5152 0.9195 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6256 2.5252 -0.0374 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4570 1.9576 -0.4835 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9671 0.8026 -1.3836 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6867 3.8509 0.0847 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6394 -2.1220 -0.2685 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3734 -3.4266 -0.3753 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7124 -2.4701 0.2717 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2914 -1.8771 1.8745 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6209 -1.0391 1.5389 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3109 -2.0651 2.0920 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -3.1242 1.4381 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0663 -1.9305 3.3134 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1206 -0.7943 4.0686 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8849 -0.7229 5.2413 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6063 -1.8062 5.6649 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5609 -2.9586 4.9141 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8101 -3.0257 3.7639 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3353 2.2117 -0.2520 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8447 3.0612 -1.1809 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0388 2.8398 -2.3683 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0683 4.2625 -0.7156 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7414 -0.9748 -4.0737 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6315 -2.7398 -3.4684 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3767 -0.8458 -3.3472 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9576 0.5311 -2.4229 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4971 0.7712 -3.3978 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8297 -0.7395 -3.5938 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1536 -2.1683 -0.8563 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2802 -3.0711 -2.0841 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5528 -1.9549 -2.5523 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4965 0.5073 -3.6166 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6917 1.4909 -3.2907 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3537 -0.0263 -2.6648 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8824 2.1174 -1.0913 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5986 2.0957 0.5888 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9265 0.8260 1.6039 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3107 0.2582 -1.1063 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0187 -2.1290 0.0263 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3240 0.9572 1.0399 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0490 0.0618 1.6594 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0933 1.5393 -0.7225 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6606 2.3414 1.4859 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5190 1.7571 -1.4130 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9566 -0.5810 -1.7789 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9507 -2.9186 -0.9624 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5605 -3.3893 1.3409 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1696 -1.6248 2.8545 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1881 0.6955 2.1015 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3079 3.7071 1.4081 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4751 4.6995 2.1763 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6133 3.9464 1.2524 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5872 2.1866 -0.4532 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4581 1.1741 -1.2444 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2338 0.8184 -2.1079 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6098 4.1534 0.2787 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1332 -3.5075 -1.1374 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6769 -3.7177 0.6539 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6189 -4.2297 -0.6489 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6909 -3.4165 0.8946 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2072 -1.7379 0.8897 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4292 -2.7530 -0.5554 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3925 -2.1609 2.0829 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5633 0.0775 3.7818 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9214 0.1788 5.8300 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2155 -1.7738 6.5850 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1432 -3.7951 5.2791 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7751 -3.9309 3.1755 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8528 4.1973 0.3656 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6423 5.1780 -0.9436 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0937 4.2870 -1.2534 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3540 -0.4876 -4.6891 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1409 -3.0507 -2.9683 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 4 5 1 0 5 6 2 0 5 7 1 0 7 8 1 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 24 31 1 0 31 32 2 3 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 32 39 1 0 23 40 1 0 17 41 1 0 41 42 1 0 41 43 1 0 17 44 1 1 16 45 1 0 45 46 1 0 46 47 2 0 46 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 51 52 1 0 52 53 2 0 12 54 1 1 54 55 1 0 55 56 2 0 55 57 1 0 9 58 1 0 4 59 1 0 19 2 1 0 30 25 1 0 38 33 1 0 53 48 1 0 41 3 1 0 15 7 1 0 14 11 1 0 1 60 1 0 1 61 1 0 1 62 1 0 4 63 1 6 8 64 1 0 8 65 1 0 8 66 1 0 9 67 1 6 10 68 1 0 10 69 1 0 11 70 1 6 13 71 1 0 13 72 1 0 15 73 1 0 16 74 1 0 18 75 1 0 18 76 1 0 19 77 1 0 23 78 1 1 24 79 1 6 26 80 1 0 27 81 1 0 28 82 1 0 29 83 1 0 30 84 1 0 34 85 1 0 35 86 1 0 36 87 1 0 37 88 1 0 38 89 1 0 39 90 1 0 40 91 1 0 42 92 1 0 42 93 1 0 42 94 1 0 43 95 1 0 43 96 1 0 43 97 1 0 44 98 1 0 49 99 1 0 50100 1 0 51101 1 0 52102 1 0 53103 1 0 57104 1 0 57105 1 0 57106 1 0 58107 1 0 59108 1 0 M END

Standard InCHIKey	TYLVGQKNNUHXIP-DAYPOXPHSA-N
Standard InCHI	InChI=1S/C45H49NO13/c1-24-29(57-41(54)35(50)33(26-15-9-6-10-16-26)46-39(52)27-17-11-7-12-18-27)22-45(55)38(58-40(53)28-19-13-8-14-20-28)36-43(5,37(51)34(49)32(24)42(45,3)4)30(48)21-31-44(36,23-56-31)59-25(2)47/h6-20,29-31,33-36,38,48-50,55H,21-23H2,1-5H3,(H,46,52)/t29?,30-,31+,33-,34+,35+,36?,38?,43+,44-,45+/m0/s1
SMILES	CC1=C2[C@H](C(=O)[C@]3(C)[C@H](C[C@@H]4[C@@](CO4)(C3C([C@](CC1OC(=O)[C@@H]([C@H](c1ccccc1)N=C(c1ccccc1)O)O)(C2(C)C)O)OC(=O)c1ccccc1)OC(=O)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	811.32	Volume:	812.703 ? Van der Waals volume.
Dense:	0.998	LogP:	2.72 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.682 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.828 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	43.0
TPSA:	218.71 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	5.0	Rings:	7.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.069	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.039	Fsp³:	0.444
MCE-18:	173.4 ? 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:	0
Colloidal aggregators:	0.681	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.09 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.602 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.028	Promiscuous compounds:	0.014

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.683	MDCK Permeability:	-5.062
Pgp-inhibitor:	0.661	Pgp-substrate:	1.0
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):	0.001
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.998
Plasma Protein Binding (PPB):	96.072%	Volume Distribution (VD):	0.103
Fu:	3.263% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.983	BCRP inhibitor:	0.0
BSEP inhibitor:	0.71

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.169
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.692 ? 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):

2.167

Half-life (T1/2):

2.883

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.051
Human Hepatotoxicity (H-HT):	0.989	Drug-induced Liver Injury (DILI):	0.977
AMES Toxicity:	0.759	Rat Oral Acute Toxicity:	0.799
Maximum Recommended Daily Dose:	0.858	Skin Sensitization:	1.0
Carcinogencity:	0.05	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.092
Drug-induced Neurotoxicity:	0.988	Ototoxicity:	0.974
Hematotoxicity:	0.678	Drug-induced Nephrotoxicity:	0.996
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.251
A549 Cytotoxicity:	0.891	Hek293 Cytotoxicity:	0.879
BCF:	0.499 ? 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:	3.314 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.001 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.243 ? 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]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23265441]
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]
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]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO5067	Taxus baccata	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

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

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 NPC14752 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	11018
0.1-0.2	36590
0.2-0.3	2095
0.3-0.4	86
0.4-0.5	11
0.5-0.6	17
0.6-0.7	19
0.7-0.8	1
0.8-0.85	9
0.85-0.9	2
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC321072
1.0	High Similarity	NPC215892
1.0	High Similarity	NPC242662
0.8526	High Similarity	NPC102167
0.8526	High Similarity	NPC488127
0.8438	Intermediate Similarity	NPC453583
0.8351	Intermediate Similarity	NPC471754
0.8351	Intermediate Similarity	NPC479183
0.8351	Intermediate Similarity	NPC479181
0.8247	Intermediate Similarity	NPC208553
0.8247	Intermediate Similarity	NPC181964
0.8247	Intermediate Similarity	NPC307628
0.8247	Intermediate Similarity	NPC191193
0.8144	Intermediate Similarity	NPC478328
0.7778	Intermediate Similarity	NPC327699
0.7383	Intermediate Similarity	NPC289383
0.7184	Intermediate Similarity	NPC317882
0.7157	Intermediate Similarity	NPC473300
0.7115	Intermediate Similarity	NPC33372
0.7115	Intermediate Similarity	NPC67246
0.7048	Intermediate Similarity	NPC478329
0.7019	Intermediate Similarity	NPC471623
0.6952	Remote Similarity	NPC324251
0.6952	Remote Similarity	NPC206211
0.6887	Remote Similarity	NPC487360
0.6887	Remote Similarity	NPC479182
0.6887	Remote Similarity	NPC479180
0.6887	Remote Similarity	NPC471629
0.6887	Remote Similarity	NPC306001
0.6857	Remote Similarity	NPC453588
0.6789	Remote Similarity	NPC487361
0.6759	Remote Similarity	NPC275170
0.6697	Remote Similarity	NPC486061
0.6697	Remote Similarity	NPC486060
0.6466	Remote Similarity	NPC472375
0.6404	Remote Similarity	NPC116862
0.6293	Remote Similarity	NPC479186
0.625	Remote Similarity	NPC229545
0.625	Remote Similarity	NPC248265
0.625	Remote Similarity	NPC134685
0.6091	Remote Similarity	NPC603171
0.5905	Remote Similarity	NPC603140
0.5877	Remote Similarity	NPC471606
0.5856	Remote Similarity	NPC473490
0.5804	Remote Similarity	NPC473400
0.5766	Remote Similarity	NPC36607
0.57	Remote Similarity	NPC605573
0.5664	Remote Similarity	NPC473558
0.562	Remote Similarity	NPC472391
0.562	Remote Similarity	NPC479173
0.561	Remote Similarity	NPC479184
0.5455	Remote Similarity	NPC472392
0.5447	Remote Similarity	NPC479185
0.534	Remote Similarity	NPC155329
0.534	Remote Similarity	NPC11588
0.534	Remote Similarity	NPC114357
0.5146	Remote Similarity	NPC197037
0.5146	Remote Similarity	NPC91730

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC14752 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3195
0.1-0.2	5777
0.2-0.3	165
0.3-0.4	0
0.4-0.5	3
0.5-0.6	5
0.6-0.7	1
0.7-0.8	1
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8526	High Similarity	NPD8360	Approved
0.8526	High Similarity	NPD8361	Phase 4
0.8247	Intermediate Similarity	NPD8485	Phase 4
0.7404	Intermediate Similarity	NPD8486	Phase 1
0.6147	Remote Similarity	NPD8424	Phase 3
0.5946	Remote Similarity	NPD8435	Phase 4
0.5667	Remote Similarity	NPD8404	Phase 2
0.5565	Remote Similarity	NPD8462	Phase 2
0.5345	Remote Similarity	NPD8368	Phase 2
0.5294	Remote Similarity	NPD8434	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