NPASS Compound

Natural Product: NPC221751

Natural Product ID	NPC221751
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BUHZTPLXMFRPCK-CKCUUXPSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101683332
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

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 58 61 0 0 0 0 0 0 0 0999 V2000 -5.0378 -0.3649 3.1137 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0745 -0.8513 2.0631 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8139 -0.5729 2.3076 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3414 0.1387 3.4730 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0642 0.5885 4.4195 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8973 0.2286 3.3357 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4891 -0.3640 2.1969 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9666 -0.3880 1.8603 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2795 0.2291 0.6978 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6157 0.2264 0.3550 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9147 -0.4417 -0.9430 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1278 0.0168 -1.6548 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5719 1.4146 -1.3224 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3983 1.6852 0.1711 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7379 3.1587 0.3676 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9552 3.8622 -0.5595 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0443 1.5498 0.4161 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9523 1.5393 -1.5732 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9411 -0.0345 -3.0388 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0134 -1.8245 -0.7687 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6385 -0.9145 1.4856 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8832 -0.2728 0.1374 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8489 -1.0697 -0.7078 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2890 -0.8737 -0.3809 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7020 -1.5751 0.8979 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6392 -0.3997 -2.0755 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9746 -1.3485 -3.1970 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1879 -0.0925 -2.0066 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4712 0.2571 -2.9671 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7520 -0.2563 -0.6985 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0761 -0.6563 2.7955 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8268 -0.8915 4.0449 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0455 0.7261 3.1983 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2415 0.7121 4.0611 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1809 -1.4917 1.7042 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6148 -0.1246 2.7199 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1598 -0.3158 1.1632 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0145 -0.2874 -1.6081 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0181 -0.6478 -1.4463 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0380 2.2002 -1.8614 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0339 1.0259 0.7875 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8001 3.3599 0.0901 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4918 3.5176 1.3753 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4967 4.4733 -1.1191 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4309 0.7096 -1.2947 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5184 -0.6958 -3.4831 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4772 -2.0895 0.0420 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5867 -2.0320 1.3893 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3013 0.7301 0.2805 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6004 -2.1307 -0.7743 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8902 -1.2920 -1.1994 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5437 0.2011 -0.2871 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2869 -2.5924 0.9218 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7849 -1.5214 0.9947 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2652 0.5168 -2.0777 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0233 -1.1462 -3.5002 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8803 -2.4113 -2.8965 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3360 -1.0968 -4.0670 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 2 0 4 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 14 17 1 0 13 18 1 0 12 19 1 0 11 20 1 0 7 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 23 26 1 0 26 27 1 0 26 28 1 0 28 29 2 0 28 30 1 0 25 2 1 0 21 3 1 0 30 22 1 0 17 10 1 0 1 31 1 0 1 32 1 0 1 33 1 0 6 34 1 0 8 35 1 0 8 36 1 0 10 37 1 1 11 38 1 6 12 39 1 6 13 40 1 6 14 41 1 1 15 42 1 0 15 43 1 0 16 44 1 0 18 45 1 0 19 46 1 0 20 47 1 0 21 48 1 6 22 49 1 1 23 50 1 6 24 51 1 0 24 52 1 0 25 53 1 0 25 54 1 0 26 55 1 1 27 56 1 0 27 57 1 0 27 58 1 0 M END

Standard InCHIKey	BUHZTPLXMFRPCK-CKCUUXPSSA-N
Standard InCHI	InChI=1S/C21H28O9/c1-8-3-4-11-9(2)20(27)30-19(11)15-10(5-12(23)14(8)15)7-28-21-18(26)17(25)16(24)13(6-22)29-21/h5,9,11,13,15-19,21-22,24-26H,3-4,6-7H2,1-2H3/t9-,11-,13+,15-,16+,17-,18+,19-,21+/m0/s1
SMILES	CC1=C2C(=O)C=C(CO[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)[C@@H]2[C@@H]2[C@@H](CC1)[C@H](C)C(=O)O2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	424.17	Volume:	406.113 ? Van der Waals volume.
Dense:	1.044	LogP:	-0.395 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.3 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.732 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	23.0
TPSA:	142.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	4.0	Rings:	4.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.427	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.852	Fsp³:	0.714
MCE-18:	67.889 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.623	Fluc inhibitor:	0.129 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.324 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.124	Promiscuous compounds:	0.337

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.898	MDCK Permeability:	-5.2
Pgp-inhibitor:	0.092	Pgp-substrate:	0.573
PAMPA:	0.859 ? 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):	0.366
20% Bioavailability (F20%):	0.02	30% Bioavailability (F30%):	0.984
50% Bioavailability (F50%):	0.687

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.422
Plasma Protein Binding (PPB):	72.491%	Volume Distribution (VD):	-0.262
Fu:	26.623% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.014
BSEP inhibitor:	0.301

ADMET: Metabolism

CYP1A2-inhibitor:	0.29	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.227	CYP3A4-substrate:	0.185
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.71
HLM stability:	0.086 ? 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):

2.171

Half-life (T1/2):

2.494

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.033
Human Hepatotoxicity (H-HT):	0.765	Drug-induced Liver Injury (DILI):	0.871
AMES Toxicity:	0.823	Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.033	Skin Sensitization:	0.999
Carcinogencity:	0.318	Eye Corrosion:	0.0
Eye Irritation:	0.068	Respiratory Toxicity:	0.009
Drug-induced Neurotoxicity:	0.09	Ototoxicity:	0.945
Hematotoxicity:	0.738	Drug-induced Nephrotoxicity:	0.949
Genotoxicity:	0.847	RPMI-8226 Immunitoxicity:	0.197
A549 Cytotoxicity:	0.455	Hek293 Cytotoxicity:	0.153
BCF:	0.528 ? 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:	3.22 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.796 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.98 ? 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
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11627-001-0052-8]
NPO2465	Justicia glauca	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1667412]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341288]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24784222]
NPO7872	Buxus madagascarica	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12407	Herba cichorii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29531	Lupinus cosentinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO513	Agathosma scaberula	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13123	Balanophora harlandii	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO245	Euphorbia biglandulosa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17549	Polemonium caeruleum	Species	Polemoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2161	Strychnos ledermannii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1584	Tolypothrix tjipanasensis	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4892	Viburnum davidii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11801	Strychnos axillaris	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3927	Callyspongia fistularis	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28557	Cacalia hastata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2465	Justicia glauca	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12407	Herba cichorii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9787	Krameria grayi	Species	Krameriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO245	Euphorbia biglandulosa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29531	Lupinus cosentinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13123	Balanophora harlandii	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1584	Tolypothrix tjipanasensis	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17549	Polemonium caeruleum	Species	Polemoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4892	Viburnum davidii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO513	Agathosma scaberula	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11501	Carphephorus corymbosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8864	Ceratostomella fimbriata	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28557	Cacalia hastata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3927	Callyspongia fistularis	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2465	Justicia glauca	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11801	Strychnos axillaris	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7872	Buxus madagascarica	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2161	Strychnos ledermannii	Species	Loganiaceae	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 NPC221751 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	17129
0.1-0.2	27417
0.2-0.3	4778
0.3-0.4	505
0.4-0.5	25
0.5-0.6	4
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	Natural Product ID
0.5781	Remote Similarity	NPC237540
0.5397	Remote Similarity	NPC15975
0.5397	Remote Similarity	NPC195785
0.5263	Remote Similarity	NPC54731

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC221751 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6381
0.1-0.2	2644
0.2-0.3	119
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