NPASS Compound

Natural Product: NPC105591

Natural Product ID	NPC105591
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2R,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(8-Hydroxy-6-Methyl-9,10-Dioxoanthracen-1-Yl)Oxyoxan-2-Yl]Methyl 3,4,5-Trihydroxybenzoate
IUPAC Name	[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(8-hydroxy-6-methyl-9,10-dioxoanthracen-1-yl)oxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL109609
PubChem CID	5315852
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

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 65 69 0 0 0 0 0 0 0 0999 V2000 -6.8904 2.0071 3.7464 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9050 1.6023 2.7085 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5915 1.4055 3.0450 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 1.0268 2.0744 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3425 0.8356 2.4564 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0334 0.8363 0.7589 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3540 1.0327 0.4130 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2651 1.4096 1.3810 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7344 0.8283 -0.9906 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9216 1.0010 -1.3217 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7555 0.4287 -2.0025 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4336 0.2314 -1.6614 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0522 0.4325 -0.2717 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8701 0.2673 0.0949 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4930 -0.1511 -2.6243 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8643 -0.3396 -3.9327 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2094 -0.1394 -4.2814 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1127 0.2354 -3.3198 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2233 -0.3230 -2.2062 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0763 -0.7219 -2.9103 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4545 -1.7997 -2.2876 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -1.7073 -1.5839 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3578 -1.2036 -0.1550 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6331 -1.1380 0.4535 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8572 -0.7403 1.7521 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8787 -0.4103 2.4682 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2247 -0.7159 2.2545 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2876 -1.0584 1.4492 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5706 -1.0291 1.9519 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6286 -1.3786 1.1239 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8135 -0.6632 3.2469 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7460 -0.3199 4.0541 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4444 -0.3441 3.5633 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9903 0.0505 5.3661 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1169 -0.6474 3.7117 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7671 -1.0428 -2.2301 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2843 -0.1133 -3.2909 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9096 0.4173 -3.0134 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5022 1.3199 -4.0195 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1976 0.9484 -3.3900 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6832 -1.9817 -2.6992 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4745 2.8435 4.3434 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1813 1.1466 4.3815 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8048 2.3890 3.2070 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2641 1.5437 4.0672 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9461 -0.1051 2.4607 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2962 1.5618 1.1075 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1980 -0.6341 -4.7360 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5273 -0.2812 -5.3158 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1706 0.4014 -3.5537 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4509 -0.9730 -3.9569 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9420 -2.7891 -1.3971 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7616 -1.9832 0.3681 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8040 -0.2733 -0.1045 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1104 -1.3532 0.4131 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0282 -0.7266 0.4489 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6471 -0.0700 4.2260 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4665 0.9073 5.6300 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8400 -0.2417 3.1004 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3156 -0.4458 -1.4557 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2786 -0.6050 -4.3075 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8820 0.9920 -2.0847 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8114 0.9987 -4.9108 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9999 1.6597 -2.7192 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2770 -2.3103 -1.9809 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 4 6 2 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 12 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 15 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 2 0 28 29 1 0 29 30 1 0 29 31 2 0 31 32 1 0 32 33 2 0 32 34 1 0 31 35 1 0 22 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 37 40 1 0 36 41 1 0 8 2 1 0 18 11 1 0 38 20 1 0 13 6 1 0 33 27 1 0 1 42 1 0 1 43 1 0 1 44 1 0 3 45 1 0 5 46 1 0 8 47 1 0 16 48 1 0 17 49 1 0 18 50 1 0 20 51 1 6 22 52 1 1 23 53 1 0 23 54 1 0 28 55 1 0 30 56 1 0 33 57 1 0 34 58 1 0 35 59 1 0 36 60 1 1 37 61 1 6 38 62 1 1 39 63 1 0 40 64 1 0 41 65 1 0 M END

Standard InCHIKey	KBGOIDOUXFNKHS-DPALUKPESA-N
Standard InCHI	InChI=1S/C28H24O13/c1-10-5-13-19(14(29)6-10)24(35)20-12(21(13)32)3-2-4-17(20)40-28-26(37)25(36)23(34)18(41-28)9-39-27(38)11-7-15(30)22(33)16(31)8-11/h2-8,18,23,25-26,28-31,33-34,36-37H,9H2,1H3/t18-,23-,25+,26-,28-/m1/s1
SMILES	Cc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(ccc1)O[C@@H]1O[C@H](COC(=O)c2cc(O)c(c(c2)O)O)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	568.12	Volume:	532.697 ? Van der Waals volume.
Dense:	1.066	LogP:	2.091 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.224 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.663 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	31.0
TPSA:	220.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.13	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.124	Fsp³:	0.25
MCE-18:	111.714 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.651	Fluc inhibitor:	0.225 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.422 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.974 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.07	Promiscuous compounds:	0.599

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.217	MDCK Permeability:	-5.245
Pgp-inhibitor:	0.004	Pgp-substrate:	0.005
PAMPA:	0.995 ? 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):	0.012
20% Bioavailability (F20%):	0.385	30% Bioavailability (F30%):	0.992
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.992
Plasma Protein Binding (PPB):	94.488%	Volume Distribution (VD):	-0.102
Fu:	5.081% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.149
BSEP inhibitor:	0.029

ADMET: Metabolism

CYP1A2-inhibitor:	0.026	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.585 ? 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):

2.725

Half-life (T1/2):

3.304

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.748
Human Hepatotoxicity (H-HT):	0.318	Drug-induced Liver Injury (DILI):	0.991
AMES Toxicity:	0.964	Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.212	Skin Sensitization:	1.0
Carcinogencity:	0.549	Eye Corrosion:	0.0
Eye Irritation:	0.518	Respiratory Toxicity:	0.023
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.983
Hematotoxicity:	0.07	Drug-induced Nephrotoxicity:	0.1
Genotoxicity:	0.975	RPMI-8226 Immunitoxicity:	0.053
A549 Cytotoxicity:	0.996	Hek293 Cytotoxicity:	0.539
BCF:	1.066 ? 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:	3.918 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.225 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.744 ? 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
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	Flowers	Tantempango, Hidalgo, Mexico	2019-May	DOI[10.1007/s11130-020-00822-2]
NPO88	Rheum undulatum	Species	Polygonaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10714491]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757709]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076555]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11430011]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11459643]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517743]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16297615]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	root	n.a.	PMID[16564530]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[17345316]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17685627]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18543151]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23078294]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23513740]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24358188]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26521454]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29359942]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31944695]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[7714535]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277318]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778246]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12327	Senna occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7672	Senna tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18640	Tectona grandis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO88	Rheum undulatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO574	Rumex nepalensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18339	Rheum wittrocki	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO574	Rumex nepalensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18640	Tectona grandis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7672	Senna tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18339	Rheum wittrocki	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18640	Tectona grandis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12327	Senna occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3980	Frangula purshiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO574	Rumex nepalensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18640	Tectona grandis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18339	Rheum wittrocki	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO574	Rumex nepalensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7672	Senna tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO88	Rheum undulatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18640	Tectona grandis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO574	Rumex nepalensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO88	Rheum undulatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3980	Frangula purshiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7672	Senna tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13107	Rumex patientia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12327	Senna occidentalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18951	Ligusticum sinense	Species	Apiaceae	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
Inhibition	1

Activity Type	# Activity
Organism	2

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
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	100000.0	nM	PMID[10714491]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	31.0	%	PMID[10714491]

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 NPC105591 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	18290
0.1-0.2	28312
0.2-0.3	2831
0.3-0.4	351
0.4-0.5	56
0.5-0.6	13
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7733	Intermediate Similarity	NPC178281
0.6753	Remote Similarity	NPC278329
0.575	Remote Similarity	NPC166277
0.5696	Remote Similarity	NPC484156
0.5663	Remote Similarity	NPC101116
0.561	Remote Similarity	NPC1913
0.5604	Remote Similarity	NPC46958
0.5488	Remote Similarity	NPC472859
0.5422	Remote Similarity	NPC25389
0.5412	Remote Similarity	NPC160780
0.5357	Remote Similarity	NPC271385
0.5275	Remote Similarity	NPC479375
0.5233	Remote Similarity	NPC76128
0.5111	Remote Similarity	NPC289346
0.5104	Remote Similarity	NPC479369

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC105591 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3806
0.1-0.2	5225
0.2-0.3	109
0.3-0.4	8
0.4-0.5	2
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