NPASS Compound

Natural Product: NPC261411

Natural Product ID	NPC261411
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Tellimagrandin Ii
IUPAC Name	n.a.
Synonyms	tellimagrandin II
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL510512
PubChem CID	11766372
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 97103 0 0 0 0 0 0 0 0999 V2000 -0.4246 0.4515 4.0373 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1195 1.5714 3.2959 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3219 2.6743 3.9820 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4528 2.6586 5.3498 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1505 1.5422 6.1048 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2965 0.4199 5.4301 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6028 -0.7009 6.1590 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2887 1.5483 7.4688 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9017 3.7867 6.0253 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2505 1.6036 1.8442 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0483 2.6576 1.2042 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6911 0.5244 1.1200 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7899 0.6281 -0.2884 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1558 -0.3811 -0.8809 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3314 -0.6945 -2.2753 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7710 -1.4298 -3.0245 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8409 -1.4939 -2.1755 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0705 -2.0094 -2.2415 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5002 -2.5925 -3.2108 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8955 -1.8353 -1.0485 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0315 -3.0528 -0.3550 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6917 -3.1028 0.8424 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2199 -1.9554 1.3616 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0781 -0.7825 0.6703 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4101 -0.6794 -0.5690 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4422 0.6343 -1.1974 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3949 1.4160 -1.5863 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6985 2.6802 -2.1127 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9779 3.1580 -2.2552 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0269 2.3803 -1.8724 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7485 1.1403 -1.3543 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7799 0.2793 -0.9464 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3629 2.7911 -1.9847 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1908 4.4243 -2.7859 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9981 1.0763 -1.5952 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1785 1.7358 -2.2623 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5117 0.0179 -0.8837 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5919 0.4186 1.1603 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8915 -1.9535 2.5651 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7996 -4.3352 1.4903 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5034 -1.4395 -2.2542 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3703 -1.0576 -1.2528 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1582 0.3955 -0.8106 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5318 1.1754 -1.9154 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6890 1.9440 -1.9531 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3956 1.8974 -0.9144 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0208 2.7251 -3.1191 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1728 3.4723 -3.1326 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4999 4.2277 -4.2528 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6746 4.2309 -5.3494 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5280 3.4914 -5.3445 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2029 2.7350 -4.2198 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6740 3.4821 -6.4523 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0132 5.0008 -6.4847 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6496 4.9753 -4.2709 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4176 -1.9367 -0.1500 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5354 -2.6577 0.1813 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5532 -2.4892 -0.5742 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6262 -3.5745 1.3091 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5694 -3.8018 2.1533 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7174 -4.6794 3.2035 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8866 -5.3604 3.4676 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9337 -5.1046 2.5919 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8061 -4.2333 1.5391 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1310 -5.7827 2.8375 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9799 -6.2308 4.5372 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6223 -4.8822 4.0361 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7774 -0.4486 3.5564 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5751 3.5787 3.4540 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4921 -0.9359 6.5559 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1115 2.2111 8.1008 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3639 4.5626 5.5541 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4701 1.6329 -0.6469 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1531 -1.3376 -0.2715 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5591 0.2689 -2.7717 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9718 -0.9580 -4.0091 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3769 -2.4586 -3.2657 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5908 -3.9506 -0.8370 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8470 3.3238 -2.4247 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5839 0.0758 -1.5229 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0552 2.4308 -1.3501 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6980 5.2410 -2.4255 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2781 0.4040 1.9273 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8733 -2.0971 2.6808 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2937 -5.1028 1.0591 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3971 -1.1176 -1.7307 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9656 0.5506 -0.0348 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8761 3.5187 -2.2999 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2790 2.1707 -4.2817 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4527 2.5674 -6.8385 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3269 5.1948 -7.2001 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4873 4.6177 -3.8308 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6410 -3.2695 1.9536 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6718 -4.0946 0.9081 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1622 -6.6408 3.3679 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4908 -5.9560 5.3912 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5535 -5.7246 4.6210 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 5 8 1 0 4 9 1 0 2 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 30 33 1 0 29 34 1 0 27 35 1 0 35 36 2 0 35 37 1 0 24 38 1 0 23 39 1 0 22 40 1 0 15 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 51 53 1 0 50 54 1 0 49 55 1 0 42 56 1 0 56 57 1 0 57 58 2 0 57 59 1 0 59 60 2 0 60 61 1 0 61 62 2 0 62 63 1 0 63 64 2 0 63 65 1 0 62 66 1 0 61 67 1 0 6 1 1 0 43 13 1 0 52 47 1 0 64 59 1 0 37 14 1 0 25 20 1 0 31 26 1 0 1 68 1 0 3 69 1 0 7 70 1 0 8 71 1 0 9 72 1 0 13 73 1 6 14 74 1 1 15 75 1 6 16 76 1 0 16 77 1 0 21 78 1 0 28 79 1 0 32 80 1 0 33 81 1 0 34 82 1 0 38 83 1 0 39 84 1 0 40 85 1 0 42 86 1 0 43 87 1 1 48 88 1 0 52 89 1 0 53 90 1 0 54 91 1 0 55 92 1 0 60 93 1 0 64 94 1 0 65 95 1 0 66 96 1 0 67 97 1 0 M END

Standard InCHIKey	JCGHAEBIBSEQAD-WZASNERQSA-N
Standard InCHI	InChI=1S/C41H30O26/c42-15-1-10(2-16(43)26(15)50)36(57)65-34-33-23(9-62-39(60)13-7-21(48)29(53)31(55)24(13)25-14(40(61)64-33)8-22(49)30(54)32(25)56)63-41(67-38(59)12-5-19(46)28(52)20(47)6-12)35(34)66-37(58)11-3-17(44)27(51)18(45)4-11/h1-8,23,33-35,41-56H,9H2/t23-,33-,34+,35-,41?/m1/s1
SMILES	c1c(cc(c(c1O)O)O)C(=O)O[C@H]1[C@H]2[C@@H](COC(=O)c3cc(c(c(c3-c3c(cc(c(c3O)O)O)C(=O)O2)O)O)O)OC([C@@H]1OC(=O)c1cc(c(c(c1)O)O)O)OC(=O)c1cc(c(c(c1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	938.1	Volume:	833.613 ? Van der Waals volume.
Dense:	1.125	LogP:	-0.043 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.454 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.624 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	49.0
TPSA:	444.18 ? Topological Polar Surface Area.	H-Bond Acceptor:	26.0
H-Bond Donor:	15.0	Rings:	7.0
Heavy Atoms:	26.0

MedChem Properties

QED Drug-Likeness Score:	0.065	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.589	Fsp³:	0.146
MCE-18:	172.532 ? 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:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.997	Fluc inhibitor:	0.094 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.444 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.666 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.69	Promiscuous compounds:	0.998

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.781	MDCK Permeability:	-4.779
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
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):	0.0
20% Bioavailability (F20%):	0.991	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	74.203%	Volume Distribution (VD):	-0.142
Fu:	14.995% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.558
OATP1B3 inhibitor:	0.715	BCRP inhibitor:	0.259
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.012
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.008 ? 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):

4.871

Half-life (T1/2):

4.828

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.996
Human Hepatotoxicity (H-HT):	0.062	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.973	Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.94	Skin Sensitization:	1.0
Carcinogencity:	0.111	Eye Corrosion:	0.0
Eye Irritation:	0.985	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.321
BCF:	0.052 ? 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:	3.34 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.138 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.194 ? 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
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF00579992]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/j.foodchem.2010.03.088]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodcont.2014.02.001]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1021/np50028a032]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[10993241]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402962]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16926516]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[20467822]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[22834923]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[24063567]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24461297]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[26977531]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30395460]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31401871]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31738062]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32569471]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34332066]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34486118]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34770801]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35344272]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36558111]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36985392]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37571040]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37836118]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37917799]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38677581]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39064968]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39065796]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39684253]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39699537]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4013523]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[8759159]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759159]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8904847]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834152]
NPO31117	Feijoa sellowiana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO1879	Feijoa sellowiana	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO1879	Feijoa sellowiana	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO31117	Feijoa sellowiana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9776	Tellima grandifolia	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1879	Feijoa sellowiana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9776	Tellima grandifolia	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31117	Feijoa sellowiana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9776	Tellima grandifolia	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1879	Feijoa sellowiana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	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	4
Ki	2
APTT	2
TT	2
PT	2

Activity Type	# Activity
Individual protein	6
Tissue	6

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2533	Individual protein	Coagulation factor X	Homo sapiens	IC50	=	210.0	nM	PMID[9834152]
NPT2533	Individual protein	Coagulation factor X	Homo sapiens	Ki	=	440.0	nM	PMID[9834152]
NPT2534	Individual protein	Thrombin	Bos taurus	IC50	=	14.0	nM	PMID[9834152]
NPT2534	Individual protein	Thrombin	Bos taurus	IC50	=	70.0	nM	PMID[9834152]
NPT2534	Individual protein	Thrombin	Bos taurus	Ki	=	420.0	nM	PMID[9834152]
NPT740	Individual protein	Beta-secretase 1	Homo sapiens	IC50	=	20230.0	nM	PMID[35398739]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	APTT	>	300.0	s	PMID[9834152]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	TT	>	300.0	s	PMID[9834152]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	PT	>	300.0	s	PMID[9834152]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	APTT	=	45.7	s	PMID[9834152]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	TT	=	18.7	s	PMID[9834152]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	PT	=	11.9	s	PMID[9834152]

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 NPC261411 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	25317
0.1-0.2	23840
0.2-0.3	527
0.3-0.4	76
0.4-0.5	35
0.5-0.6	19
0.6-0.7	24
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC43918
1.0	High Similarity	NPC190204
0.9815	High Similarity	NPC469651
0.9811	High Similarity	NPC47521
0.7963	Intermediate Similarity	NPC114791
0.7963	Intermediate Similarity	NPC104222
0.7963	Intermediate Similarity	NPC210501
0.7963	Intermediate Similarity	NPC318826
0.7963	Intermediate Similarity	NPC141331
0.7571	Intermediate Similarity	NPC112211
0.7571	Intermediate Similarity	NPC254925
0.7361	Intermediate Similarity	NPC223534
0.7361	Intermediate Similarity	NPC483712
0.7361	Intermediate Similarity	NPC158214
0.7361	Intermediate Similarity	NPC214202
0.726	Intermediate Similarity	NPC290289
0.7123	Intermediate Similarity	NPC97924
0.6974	Remote Similarity	NPC187632
0.6974	Remote Similarity	NPC240200
0.6974	Remote Similarity	NPC488885
0.6944	Remote Similarity	NPC40078
0.6912	Remote Similarity	NPC8940
0.6795	Remote Similarity	NPC194439
0.6795	Remote Similarity	NPC33724
0.6769	Remote Similarity	NPC302170
0.6769	Remote Similarity	NPC311389
0.6625	Remote Similarity	NPC116108
0.6463	Remote Similarity	NPC488884
0.6406	Remote Similarity	NPC175793
0.6406	Remote Similarity	NPC159913
0.6386	Remote Similarity	NPC488887
0.6386	Remote Similarity	NPC488886
0.6265	Remote Similarity	NPC471091
0.6176	Remote Similarity	NPC149300
0.6118	Remote Similarity	NPC469649
0.6092	Remote Similarity	NPC469652
0.6092	Remote Similarity	NPC486025
0.6092	Remote Similarity	NPC486024
0.6061	Remote Similarity	NPC488888
0.6027	Remote Similarity	NPC470271
0.6023	Remote Similarity	NPC260521
0.5976	Remote Similarity	NPC189312
0.597	Remote Similarity	NPC291957
0.5955	Remote Similarity	NPC93065
0.5955	Remote Similarity	NPC220876
0.5824	Remote Similarity	NPC31208
0.5824	Remote Similarity	NPC160543
0.5694	Remote Similarity	NPC217781
0.5667	Remote Similarity	NPC201814
0.5638	Remote Similarity	NPC174140
0.5625	Remote Similarity	NPC31034
0.5588	Remote Similarity	NPC14030
0.5543	Remote Similarity	NPC119094
0.5543	Remote Similarity	NPC173872
0.5244	Remote Similarity	NPC470272
0.52	Remote Similarity	NPC470898
0.52	Remote Similarity	NPC76264
0.5167	Remote Similarity	NPC610546
0.5152	Remote Similarity	NPC238419
0.5152	Remote Similarity	NPC172419

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC261411 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6298
0.1-0.2	2838
0.2-0.3	13
0.3-0.4	1
0.4-0.5	0
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