NPASS Compound

Natural Product: NPC82070

Natural Product ID	NPC82070
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Strictosidine
IUPAC Name	methyl (2S,3R,4S)-3-ethenyl-4-[[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
Synonyms	strictosidine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL402211
PubChem CID	161336
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

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 72 76 0 0 0 0 0 0 0 0999 V2000 -7.3585 -2.0939 -2.9739 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3357 -1.1278 -2.8328 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4425 -1.4533 -1.6480 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4787 -0.4995 -1.5552 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8288 -0.3980 -0.3540 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9297 0.6110 -0.2515 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6223 0.2674 0.0477 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2256 0.7539 1.3209 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6843 2.0266 1.3809 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1894 2.4230 0.4704 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5182 1.4115 -0.5780 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7499 0.7242 -1.0660 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4125 -0.2881 -2.0907 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7916 -1.5343 -2.1364 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4402 0.3503 -0.0765 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7629 0.8855 0.4067 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4758 1.5829 -0.6680 N 0 0 0 0 0 0 0 0 0 0 0 0 4.6588 2.1865 -0.1495 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5923 1.2571 0.5781 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9912 -0.0410 0.8640 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6463 -0.2440 0.7930 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3544 -1.5307 1.1077 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5033 -2.1551 1.3802 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5376 -1.2597 1.2384 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8333 -1.6601 1.4648 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0745 -2.9616 1.8328 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0261 -3.8531 1.9723 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7114 -3.4644 1.7471 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7885 3.7539 0.4903 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4690 4.5717 1.4086 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6946 4.1970 -0.4348 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2473 5.5167 -0.3608 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8163 -0.2352 0.8125 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5303 -1.5692 0.8669 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2419 -1.7461 -0.4420 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7427 -3.0621 -0.4587 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3674 -1.5552 1.9527 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0762 -0.0198 1.9733 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9558 -2.8726 -3.4461 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7616 -1.1392 -3.7813 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8505 -0.1696 -2.6476 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9195 -2.4154 -1.9381 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3237 -1.3660 -0.1616 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5736 -0.8348 0.1337 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9277 2.7614 2.1481 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0176 1.9455 -1.4110 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2824 1.5425 -1.6510 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2500 0.1192 -2.9003 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4181 -2.0239 -1.4237 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4526 -2.1603 -2.9694 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6720 -0.3150 -0.9462 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0106 -0.2890 0.6961 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6974 1.5716 1.2477 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7318 0.8641 -1.3654 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2262 2.5812 -1.0448 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4477 3.1051 0.4514 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9358 1.7509 1.5362 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5411 1.0985 0.0140 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3797 -1.8999 1.1156 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6124 -0.9225 1.3416 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1036 -3.2497 2.0047 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2671 -4.8762 2.2662 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9052 -4.1667 1.8586 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4928 6.2382 0.0164 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1623 5.5636 0.2274 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4725 5.7926 -1.4179 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5439 0.5728 0.6106 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7583 -2.3748 0.9842 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1343 -1.0857 -0.4239 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9126 -3.3563 0.4779 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8049 -0.6638 2.0743 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1863 0.9075 2.2909 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 11 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 2 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 10 29 1 0 29 30 2 0 29 31 1 0 31 32 1 0 5 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 34 37 1 0 33 38 1 0 35 3 1 0 12 7 1 0 21 16 1 0 28 23 1 0 24 20 1 0 1 39 1 0 2 40 1 0 2 41 1 0 3 42 1 6 5 43 1 1 7 44 1 1 9 45 1 0 11 46 1 6 12 47 1 6 13 48 1 0 14 49 1 0 14 50 1 0 15 51 1 0 15 52 1 0 16 53 1 1 17 54 1 0 18 55 1 0 18 56 1 0 19 57 1 0 19 58 1 0 22 59 1 0 25 60 1 0 26 61 1 0 27 62 1 0 28 63 1 0 32 64 1 0 32 65 1 0 32 66 1 0 33 67 1 6 34 68 1 1 35 69 1 1 36 70 1 0 37 71 1 0 38 72 1 0 M END

Standard InCHIKey	XBAMJZTXGWPTRM-NTXHKPOFSA-N
Standard InCHI	InChI=1S/C27H34N2O9/c1-3-13-16(10-19-21-15(8-9-28-19)14-6-4-5-7-18(14)29-21)17(25(34)35-2)12-36-26(13)38-27-24(33)23(32)22(31)20(11-30)37-27/h3-7,12-13,16,19-20,22-24,26-33H,1,8-11H2,2H3/t13-,16+,19+,20-,22-,23+,24-,26+,27+/m1/s1
SMILES	OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@H]([C@H]2C=C)C[C@@H]2NCCc3c2[nH]c2c3cccc2)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	530.23	Volume:	515.416 ? Van der Waals volume.
Dense:	1.029	LogP:	0.771 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.216 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.65 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	29.0
TPSA:	162.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.218	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.854	Fsp³:	0.519
MCE-18:	106.098 ? 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:	0.48	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.536 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.038 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.005	Promiscuous compounds:	0.283

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.87	MDCK Permeability:	-5.155
Pgp-inhibitor:	0.001	Pgp-substrate:	0.975
PAMPA:	0.94 ? 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):	0.003
20% Bioavailability (F20%):	0.044	30% Bioavailability (F30%):	0.984
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018	MRP1:	0.909
Plasma Protein Binding (PPB):	73.875%	Volume Distribution (VD):	-0.442
Fu:	25.441% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.123
BSEP inhibitor:	0.015

ADMET: Metabolism

CYP1A2-inhibitor:	0.043	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.006
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.338
CYP3A4-inhibitor:	0.095	CYP3A4-substrate:	0.007
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.407 ? 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):

2.707

Half-life (T1/2):

2.107

ADMET: Toxicity

hERG Blockers:	0.172	hERG Blockers (10um):	0.264
Human Hepatotoxicity (H-HT):	0.75	Drug-induced Liver Injury (DILI):	0.919
AMES Toxicity:	0.979	Rat Oral Acute Toxicity:	0.483
Maximum Recommended Daily Dose:	0.751	Skin Sensitization:	1.0
Carcinogencity:	0.162	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.337
Drug-induced Neurotoxicity:	0.398	Ototoxicity:	0.964
Hematotoxicity:	0.296	Drug-induced Nephrotoxicity:	0.981
Genotoxicity:	0.984	RPMI-8226 Immunitoxicity:	0.13
A549 Cytotoxicity:	0.629	Hek293 Cytotoxicity:	0.312
BCF:	0.579 ? 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:	3.269 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.831 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.013 ? 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
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869194]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568781]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18588343]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19331340]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21070010]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21070010]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21341711]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[21341711]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27700077]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28225280]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31789520]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31804070]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1002/bit.28040]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1007/s13213-015-1074-5]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1016/j.bej.2020.107655]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1016/j.jbiotec.2013.10.017]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1016/j.mec.2022.e00215]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1016/j.meteno.2018.02.001]
NPO65045	A new engineered strain of Nicotiana benthamiana	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1016/j.scienta.2018.08.042]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1016/j.ymben.2015.07.007]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1016/j.ymben.2017.09.006]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1016/j.ymben.2019.06.004]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1016/j.ymben.2022.01.013]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1016/j.ymben.2022.11.002]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1016/j.ymben.2023.01.005]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1021/acs.jafc.9b03456]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1021/acssynbio.2c00037]
NPO65045	A new engineered strain of Nicotiana benthamiana	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1021/acssynbio.2c00434]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1021/acssynbio.5b00289]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1021/acssynbio.7b00439]
NPO65045	A new engineered strain of Nicotiana benthamiana	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1038/ncomms4606]
NPO65045	A new engineered strain of Nicotiana benthamiana	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1038/s42003-022-03904-w]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1073/pnas.1423555112]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1073/pnas.1501821112]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1128/AEM.01249-09]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1128/AEM.01983-12]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1186/s13068-018-1176-y]
NPO65045	A new engineered strain of Nicotiana benthamiana	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.3389/fpls.2022.919443]
NPO65071	A new engineered strain of Saccharomyces cerevisiae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[https://doi.org/10.34133/bdr.0002]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29352	Uncaria sinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29352	Uncaria sinensis	Species	Rubiaceae	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
Ratio	1
IC50	1
IC12	2

Activity Type	# Activity
Individual protein	1
Others	1
Organism	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3963	Individual protein	Strictosidine beta-glucosidase	Catharanthus roseus	Ratio	=	1.0	/min	PMID[18061449]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	>	250.0	ug ml-1	PMID[12880329]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	100.0	ug ml-1	PMID[12880329]
NPT1	Others	Radical scavenging activity	n.a.	IC50	=	56000.0	nM	PMID[15568781]

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 NPC82070 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	16013
0.1-0.2	31061
0.2-0.3	2500
0.3-0.4	210
0.4-0.5	55
0.5-0.6	11
0.6-0.7	3
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8065	Intermediate Similarity	NPC40703
0.7653	Intermediate Similarity	NPC201287
0.7653	Intermediate Similarity	NPC475271
0.7653	Intermediate Similarity	NPC601145
0.7	Intermediate Similarity	NPC476114
0.6667	Remote Similarity	NPC474905
0.6667	Remote Similarity	NPC599983
0.6132	Remote Similarity	NPC603178
0.5872	Remote Similarity	NPC199607
0.5872	Remote Similarity	NPC54591
0.578	Remote Similarity	NPC486444
0.578	Remote Similarity	NPC486448
0.578	Remote Similarity	NPC649
0.5714	Remote Similarity	NPC180804
0.5714	Remote Similarity	NPC227138
0.5714	Remote Similarity	NPC174788
0.5357	Remote Similarity	NPC84073
0.5227	Remote Similarity	NPC117596
0.5043	Remote Similarity	NPC486463

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC82070 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5008
0.1-0.2	4036
0.2-0.3	100
0.3-0.4	6
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