NPASS Compound

Natural Product: NPC279894

Natural Product ID	NPC279894
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZCSDEGFPWXFQLB-XBCUURSXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44258929
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-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 1.3551 -2.0540 0.1940 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7085 -0.6962 0.0449 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6211 0.3968 -0.3576 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3079 1.6771 0.3585 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1301 1.8518 0.7744 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9197 0.6012 0.8129 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0107 -0.4207 1.2175 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9662 0.5554 1.7788 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0890 -0.1889 1.3635 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0420 -1.5759 1.6313 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0416 -2.0599 2.2133 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1044 -2.3401 1.2388 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1318 -3.7249 1.4680 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2141 -4.4662 1.0600 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2738 -3.8662 0.4278 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2219 -2.5087 0.2156 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1524 -1.7040 0.6064 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1347 -0.4276 0.3916 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1317 0.3922 0.7467 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2450 1.8024 0.4453 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2371 2.2248 -0.4529 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4719 3.5332 -0.7738 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7010 4.5223 -0.1942 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7213 4.1453 0.6893 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4986 2.7924 1.0050 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9349 5.8485 -0.5157 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3838 -4.6294 0.0097 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0298 -4.2693 2.1111 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0844 2.4794 2.0357 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6483 2.7678 -0.4632 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9737 0.0888 -0.1460 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7239 0.1647 -1.3076 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7949 1.2350 -1.2323 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0162 0.7298 -0.5024 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6246 -0.4171 0.3804 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9944 -1.4868 -0.4503 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9792 -2.5582 -0.8664 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9289 -2.1145 -1.7613 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3462 -1.0457 -1.5828 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7745 -0.8814 1.0580 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6301 1.7602 0.2378 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2043 1.4973 -2.5575 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8140 -2.2222 1.1690 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0341 -2.2821 -0.6597 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5145 -2.8071 0.1101 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0816 -0.7996 -0.7423 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5373 0.6260 -1.4630 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9837 1.7940 1.2506 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6019 2.6315 0.1057 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2522 0.2822 -0.1881 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2270 -5.5198 1.2382 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0357 -2.0050 -0.2778 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8319 1.4370 -0.8989 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2468 3.8453 -1.4721 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1076 4.9333 1.1501 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7406 2.5897 1.7247 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4001 6.0513 -1.3901 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4609 -4.7496 -1.0104 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1766 -4.3555 1.5457 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1749 3.4357 1.8924 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6209 3.5625 0.1282 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0782 0.4487 -2.1910 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3920 2.1682 -0.7740 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8009 0.3720 -1.2247 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9090 -0.0232 1.1576 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2450 -1.9990 0.1960 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3564 -3.3282 -1.4106 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4224 -3.0952 -0.0138 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8678 -2.3387 -1.4732 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9140 -0.2919 1.8630 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2670 2.6203 -0.0587 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4715 1.3892 -3.1960 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 23 26 1 0 15 27 1 0 13 28 1 0 5 29 1 0 4 30 1 0 3 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 35 40 1 0 34 41 1 0 33 42 1 0 7 2 1 0 19 9 2 0 25 20 1 0 39 32 1 0 17 12 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 3 47 1 6 4 48 1 0 5 49 1 6 6 50 1 6 14 51 1 0 16 52 1 0 21 53 1 0 22 54 1 0 24 55 1 0 25 56 1 0 26 57 1 0 27 58 1 0 28 59 1 0 29 60 1 0 30 61 1 0 32 62 1 6 33 63 1 1 34 64 1 0 35 65 1 1 36 66 1 0 37 67 1 0 37 68 1 0 38 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 M END

Standard InCHIKey	ZCSDEGFPWXFQLB-XBCUURSXSA-N
Standard InCHI	InChI=1S/C27H30O15/c1-9-23(41-27-21(36)19(34)17(32)15(8-28)40-27)20(35)22(37)26(38-9)42-25-18(33)16-13(31)6-12(30)7-14(16)39-24(25)10-2-4-11(29)5-3-10/h2-7,9,15,17,19-23,26-32,34-37H,8H2,1H3/t9?,15?,17-,19?,20?,21-,22+,23+,26+,27+/m1/s1
SMILES	CC1[C@@H](C([C@@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(cc1)O)O)O)O)O)O[C@H]1[C@@H](C([C@@H](C(CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	0.606 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.993 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.371 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	249.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.159	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.674	Fsp³:	0.444
MCE-18:	119.436 ? 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:	0.622	Fluc inhibitor:	0.219 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.787 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.762 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.269	Promiscuous compounds:	0.488

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.539	MDCK Permeability:	-5.026
Pgp-inhibitor:	0.0	Pgp-substrate:	0.951
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%):	0.036	30% Bioavailability (F30%):	0.748
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.049
Plasma Protein Binding (PPB):	83.319%	Volume Distribution (VD):	-0.063
Fu:	14.766% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.906
OATP1B3 inhibitor:	0.993	BCRP inhibitor:	0.504
BSEP inhibitor:	0.412

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.312
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.99
HLM stability:	0.03 ? 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):

2.02

Half-life (T1/2):

4.392

ADMET: Toxicity

hERG Blockers:	0.027	hERG Blockers (10um):	0.339
Human Hepatotoxicity (H-HT):	0.349	Drug-induced Liver Injury (DILI):	0.434
AMES Toxicity:	0.588	Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.178	Skin Sensitization:	0.859
Carcinogencity:	0.035	Eye Corrosion:	0.0
Eye Irritation:	0.264	Respiratory Toxicity:	0.02
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.959
Hematotoxicity:	0.022	Drug-induced Nephrotoxicity:	0.024
Genotoxicity:	0.574	RPMI-8226 Immunitoxicity:	0.073
A549 Cytotoxicity:	0.152	Hek293 Cytotoxicity:	0.658
BCF:	0.428 ? 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:	2.987 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.637 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.655 ? 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
NPO29953	Bombax malabaricum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17764148]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[7092570]
NPO29953	Bombax malabaricum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9602	Rosa multiflora	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24237	Arthromeris mairei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9602	Rosa multiflora	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29953	Bombax malabaricum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24237	Arthromeris mairei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24237	Arthromeris mairei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9602	Rosa multiflora	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9602	Rosa multiflora	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29953	Bombax malabaricum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9602	Rosa multiflora	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24237	Arthromeris mairei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9602	Rosa multiflora	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14992	Prunus persica	Species	Rosaceae	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 NPC279894 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	21106
0.1-0.2	24292
0.2-0.3	3419
0.3-0.4	566
0.4-0.5	220
0.5-0.6	88
0.6-0.7	82
0.7-0.8	0
0.8-0.85	6
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC139320
0.9103	High Similarity	NPC471748
0.8158	Intermediate Similarity	NPC77672
0.8158	Intermediate Similarity	NPC133671
0.8158	Intermediate Similarity	NPC135391
0.8158	Intermediate Similarity	NPC78263
0.8158	Intermediate Similarity	NPC250069
0.8049	Intermediate Similarity	NPC29958
0.7763	Intermediate Similarity	NPC288084
0.775	Intermediate Similarity	NPC159579
0.747	Intermediate Similarity	NPC170052
0.747	Intermediate Similarity	NPC135846
0.7442	Intermediate Similarity	NPC605592
0.7375	Intermediate Similarity	NPC145038
0.7375	Intermediate Similarity	NPC56077
0.7375	Intermediate Similarity	NPC281131
0.7375	Intermediate Similarity	NPC253662
0.7375	Intermediate Similarity	NPC179950
0.7375	Intermediate Similarity	NPC88789
0.7375	Intermediate Similarity	NPC491374
0.7342	Intermediate Similarity	NPC111929
0.7342	Intermediate Similarity	NPC320283
0.7342	Intermediate Similarity	NPC41121
0.7333	Intermediate Similarity	NPC471669
0.716	Intermediate Similarity	NPC64305
0.7126	Intermediate Similarity	NPC470405
0.7126	Intermediate Similarity	NPC163242
0.7126	Intermediate Similarity	NPC272068
0.7	Intermediate Similarity	NPC67037
0.7	Intermediate Similarity	NPC255615
0.6988	Remote Similarity	NPC472459
0.6947	Remote Similarity	NPC189564
0.686	Remote Similarity	NPC203050
0.686	Remote Similarity	NPC225434
0.6854	Remote Similarity	NPC156869
0.6842	Remote Similarity	NPC203145
0.6829	Remote Similarity	NPC19388
0.6829	Remote Similarity	NPC240431
0.6829	Remote Similarity	NPC55786
0.6782	Remote Similarity	NPC254855
0.6782	Remote Similarity	NPC94610
0.6742	Remote Similarity	NPC173582
0.6742	Remote Similarity	NPC265885
0.6742	Remote Similarity	NPC181465
0.6742	Remote Similarity	NPC215710
0.6742	Remote Similarity	NPC473438
0.6742	Remote Similarity	NPC253788
0.6739	Remote Similarity	NPC104883
0.6739	Remote Similarity	NPC488679
0.6706	Remote Similarity	NPC60735
0.6706	Remote Similarity	NPC26230
0.6667	Remote Similarity	NPC476215
0.6632	Remote Similarity	NPC602448
0.6629	Remote Similarity	NPC471079
0.6628	Remote Similarity	NPC120099
0.6627	Remote Similarity	NPC127546
0.6627	Remote Similarity	NPC57625
0.6627	Remote Similarity	NPC173637
0.6627	Remote Similarity	NPC317489
0.6627	Remote Similarity	NPC223424
0.6627	Remote Similarity	NPC600591
0.6588	Remote Similarity	NPC325555
0.6588	Remote Similarity	NPC226304
0.6548	Remote Similarity	NPC8573
0.6548	Remote Similarity	NPC297987
0.6512	Remote Similarity	NPC182121
0.6484	Remote Similarity	NPC155877
0.6484	Remote Similarity	NPC304741
0.6471	Remote Similarity	NPC488080
0.6471	Remote Similarity	NPC169977
0.6463	Remote Similarity	NPC34531
0.6437	Remote Similarity	NPC85707
0.6437	Remote Similarity	NPC224530
0.6364	Remote Similarity	NPC292019
0.6364	Remote Similarity	NPC202908
0.6364	Remote Similarity	NPC209023
0.6364	Remote Similarity	NPC116458
0.6364	Remote Similarity	NPC246943
0.6354	Remote Similarity	NPC292929
0.6341	Remote Similarity	NPC54802
0.6341	Remote Similarity	NPC197304
0.6322	Remote Similarity	NPC175107
0.6277	Remote Similarity	NPC75574
0.625	Remote Similarity	NPC609478
0.618	Remote Similarity	NPC223747
0.6129	Remote Similarity	NPC203259
0.6129	Remote Similarity	NPC33054
0.6129	Remote Similarity	NPC176740
0.6129	Remote Similarity	NPC471725
0.6129	Remote Similarity	NPC134532
0.6129	Remote Similarity	NPC602582
0.6118	Remote Similarity	NPC135599
0.6118	Remote Similarity	NPC73855
0.6118	Remote Similarity	NPC113968
0.6118	Remote Similarity	NPC328940
0.6118	Remote Similarity	NPC277174
0.6118	Remote Similarity	NPC606877
0.6105	Remote Similarity	NPC12013
0.6105	Remote Similarity	NPC11432
0.6105	Remote Similarity	NPC477613
0.6092	Remote Similarity	NPC24043
0.6082	Remote Similarity	NPC76831
0.6082	Remote Similarity	NPC220173
0.6067	Remote Similarity	NPC259957
0.6064	Remote Similarity	NPC129264
0.6044	Remote Similarity	NPC116864
0.6044	Remote Similarity	NPC244776
0.6044	Remote Similarity	NPC95866
0.6042	Remote Similarity	NPC35119
0.6023	Remote Similarity	NPC599850
0.6022	Remote Similarity	NPC67326
0.6	Remote Similarity	NPC470125
0.5977	Remote Similarity	NPC265530
0.5955	Remote Similarity	NPC219904
0.5955	Remote Similarity	NPC129217
0.5943	Remote Similarity	NPC474522
0.5895	Remote Similarity	NPC255157
0.5895	Remote Similarity	NPC259896
0.5882	Remote Similarity	NPC219043
0.5876	Remote Similarity	NPC32641
0.5876	Remote Similarity	NPC256188
0.5876	Remote Similarity	NPC270448
0.5862	Remote Similarity	NPC249281
0.5843	Remote Similarity	NPC42773
0.5843	Remote Similarity	NPC216496
0.5843	Remote Similarity	NPC45522
0.5833	Remote Similarity	NPC296018
0.5795	Remote Similarity	NPC136042
0.5778	Remote Similarity	NPC48093
0.5758	Remote Similarity	NPC476472
0.5758	Remote Similarity	NPC294815
0.5758	Remote Similarity	NPC85751
0.5758	Remote Similarity	NPC16194
0.5758	Remote Similarity	NPC19240
0.573	Remote Similarity	NPC46420
0.5729	Remote Similarity	NPC470444
0.57	Remote Similarity	NPC221342
0.57	Remote Similarity	NPC476470
0.5698	Remote Similarity	NPC276222
0.5698	Remote Similarity	NPC274618
0.5698	Remote Similarity	NPC118284
0.5698	Remote Similarity	NPC608147
0.5684	Remote Similarity	NPC39834
0.5682	Remote Similarity	NPC289667
0.5682	Remote Similarity	NPC104677
0.5673	Remote Similarity	NPC470712
0.567	Remote Similarity	NPC61904
0.567	Remote Similarity	NPC240306
0.567	Remote Similarity	NPC64425
0.567	Remote Similarity	NPC153755
0.5652	Remote Similarity	NPC605784
0.5648	Remote Similarity	NPC156785
0.5638	Remote Similarity	NPC473682
0.5604	Remote Similarity	NPC168584
0.5588	Remote Similarity	NPC214621
0.5588	Remote Similarity	NPC34267
0.5577	Remote Similarity	NPC48984
0.5568	Remote Similarity	NPC476771
0.5556	Remote Similarity	NPC122467
0.5556	Remote Similarity	NPC480445
0.5556	Remote Similarity	NPC52550
0.5556	Remote Similarity	NPC473327
0.5545	Remote Similarity	NPC470449
0.5543	Remote Similarity	NPC101026
0.5543	Remote Similarity	NPC488077
0.5543	Remote Similarity	NPC197285
0.5543	Remote Similarity	NPC601710
0.5524	Remote Similarity	NPC25523
0.551	Remote Similarity	NPC488073
0.5506	Remote Similarity	NPC83283
0.5506	Remote Similarity	NPC143851
0.55	Remote Similarity	NPC205824
0.5495	Remote Similarity	NPC192539
0.5495	Remote Similarity	NPC21100
0.5464	Remote Similarity	NPC65563
0.5464	Remote Similarity	NPC470949
0.5463	Remote Similarity	NPC488734
0.5463	Remote Similarity	NPC488735
0.5463	Remote Similarity	NPC488732
0.5463	Remote Similarity	NPC488738
0.5455	Remote Similarity	NPC297503
0.5455	Remote Similarity	NPC103342
0.5446	Remote Similarity	NPC135831
0.5435	Remote Similarity	NPC191306
0.5435	Remote Similarity	NPC488071
0.5426	Remote Similarity	NPC276377
0.5426	Remote Similarity	NPC66087
0.5421	Remote Similarity	NPC470718
0.5417	Remote Similarity	NPC609888
0.5412	Remote Similarity	NPC78697
0.5408	Remote Similarity	NPC473571
0.5408	Remote Similarity	NPC110941
0.5408	Remote Similarity	NPC186816
0.54	Remote Similarity	NPC37668
0.5398	Remote Similarity	NPC25946
0.5391	Remote Similarity	NPC231787
0.5385	Remote Similarity	NPC84362
0.5376	Remote Similarity	NPC189913
0.5354	Remote Similarity	NPC154741
0.5347	Remote Similarity	NPC221288

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC279894 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5786
0.1-0.2	3279
0.2-0.3	68
0.3-0.4	12
0.4-0.5	4
0.5-0.6	0
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	Drug ID	Developmental Stage
0.6129	Remote Similarity	NPD6797	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