NPASS Compound

Natural Product: NPC177172

Natural Product ID	NPC177172
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Pauciflorol A
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL504167
PubChem CID	44566411
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

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 83 91 0 0 0 0 0 0 0 0999 V2000 -3.1438 1.6989 -0.9657 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7771 2.9182 -1.0683 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2654 3.5727 0.0688 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1041 2.9798 1.3009 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4598 1.7417 1.3897 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9741 1.0928 0.2441 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3170 -0.1900 0.4123 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5781 -1.2081 -0.6231 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3939 -2.3663 -0.1795 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3847 -2.8587 -0.9950 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1786 -3.9318 -0.6568 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9704 -4.5398 0.5543 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9730 -4.0668 1.4084 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1900 -2.9802 1.0341 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7825 -4.7002 2.6288 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1629 -4.4104 -1.4818 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2696 -1.6152 -1.1424 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8546 -2.4380 -2.1761 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4731 -2.6321 -2.4317 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4675 -2.0175 -1.6750 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0707 -1.1958 -0.6458 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2857 -0.6145 -0.0571 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1451 -0.1984 1.2937 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1224 -0.5014 2.2148 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0894 -0.1135 3.5379 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0454 0.6163 4.0142 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0255 0.9446 3.1048 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0891 0.5445 1.8004 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1459 0.9789 1.0585 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0676 2.0601 0.1231 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2667 3.3849 0.5799 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4715 4.4463 -0.2340 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4945 4.2649 -1.5982 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3078 3.0092 -2.0995 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0963 1.9233 -1.2292 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7083 5.3644 -2.4410 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8828 -0.2307 0.6912 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2752 -1.0053 -0.3889 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0195 1.6895 3.6449 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1249 -0.4613 4.4140 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3497 -1.5728 -0.4331 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6264 -0.8942 -0.8517 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8128 -1.1301 -0.2232 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9850 -0.5118 -0.6059 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9755 0.3803 -1.6601 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8018 0.6455 -2.3181 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6504 0.0064 -1.9059 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1866 0.9863 -2.0146 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8396 -2.0384 -1.7108 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8606 -3.0409 -2.9207 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8961 4.7975 -0.0794 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7766 1.2196 -1.8470 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9332 3.4365 -2.0135 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4877 3.5010 2.1636 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3552 1.3170 2.3773 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8206 -0.6319 1.3669 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1182 -0.7249 -1.4799 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5766 -2.4028 -1.9558 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5630 -5.3724 0.8545 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4228 -2.6207 1.6991 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5014 -5.1597 3.1338 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1411 -5.2183 -2.0604 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8004 -3.2822 -3.2518 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5155 0.2843 -0.7604 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9443 -1.0741 1.8820 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9821 0.9400 5.0455 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8094 1.4460 1.8802 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2505 3.5333 1.6635 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6179 5.4410 0.1929 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3260 2.8678 -3.1557 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0583 1.0045 -1.7314 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5476 5.2613 -3.4442 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7713 -0.8917 1.6679 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3328 1.6435 4.5823 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0446 -0.0349 4.3328 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4832 -2.4726 0.1341 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8328 -1.8210 0.6014 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9331 -0.7124 -0.0894 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7861 1.3413 -3.1444 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6987 0.2113 -2.4234 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4976 0.8766 -2.9720 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2378 -3.9220 -2.6351 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0736 5.4338 0.6804 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 11 16 1 0 8 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 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 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 33 36 1 0 29 37 1 0 37 38 1 0 27 39 1 0 25 40 1 0 22 41 1 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 45 48 1 0 41 49 1 0 18 50 1 0 3 51 1 0 6 1 1 0 37 7 1 0 47 42 1 0 14 9 1 0 38 17 1 0 49 20 1 0 38 21 2 0 28 23 1 0 35 30 1 0 1 52 1 0 2 53 1 0 4 54 1 0 5 55 1 0 7 56 1 1 8 57 1 6 10 58 1 0 12 59 1 0 14 60 1 0 15 61 1 0 16 62 1 0 19 63 1 0 22 64 1 6 24 65 1 0 26 66 1 0 29 67 1 1 31 68 1 0 32 69 1 0 34 70 1 0 35 71 1 0 36 72 1 0 37 73 1 1 39 74 1 0 40 75 1 0 41 76 1 1 43 77 1 0 44 78 1 0 46 79 1 0 47 80 1 0 48 81 1 0 50 82 1 0 51 83 1 0 M END

Standard InCHIKey	MBGBQHRAJPLAPN-ZYLOEWDGSA-N
Standard InCHI	InChI=1S/C42H32O9/c43-23-7-1-19(2-8-23)33-35(22-13-26(46)15-27(47)14-22)38-31(50)18-32-39-37(42(51-32)21-5-11-25(45)12-6-21)29-16-28(48)17-30(49)36(29)34(40(33)41(38)39)20-3-9-24(44)10-4-20/h1-18,33-35,37,40,42-50H/t33-,34+,35-,37+,40+,42-/m0/s1
SMILES	c1cc(ccc1[C@H]1[C@H](c2cc(cc(c2)O)O)c2c(cc3c4[C@@H](c5cc(cc(c5[C@@H](c5ccc(cc5)O)[C@@H]1c24)O)O)[C@H](c1ccc(cc1)O)O3)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	680.2	Volume:	689.635 ? Van der Waals volume.
Dense:	0.986	LogP:	3.734 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.42 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.832 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	47.0
TPSA:	171.07 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	8.0	Rings:	9.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.093	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.668	Fsp³:	0.143
MCE-18:	165.75 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	1.0	Fluc inhibitor:	0.796 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.13 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.332 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.671	Promiscuous compounds:	0.23

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.381	MDCK Permeability:	-4.792
Pgp-inhibitor:	0.0	Pgp-substrate:	0.317
PAMPA:	0.025 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.982	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.994
Plasma Protein Binding (PPB):	91.013%	Volume Distribution (VD):	-0.028
Fu:	12.002% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.132
BSEP inhibitor:	0.652

ADMET: Metabolism

CYP1A2-inhibitor:	0.982	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.325	CYP2C19-substrate:	0.982
CYP2C9-inhibitor:	0.926	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.07	CYP2D6-substrate:	0.993
CYP3A4-inhibitor:	0.99	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.99
HLM stability:	0.119 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

4.201

Half-life (T1/2):

3.914

ADMET: Toxicity

hERG Blockers:	0.65	hERG Blockers (10um):	0.923
Human Hepatotoxicity (H-HT):	0.979	Drug-induced Liver Injury (DILI):	0.673
AMES Toxicity:	0.711	Rat Oral Acute Toxicity:	0.558
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	0.996
Carcinogencity:	0.209	Eye Corrosion:	0.0
Eye Irritation:	0.66	Respiratory Toxicity:	0.904
Drug-induced Neurotoxicity:	0.862	Ototoxicity:	0.923
Hematotoxicity:	0.01	Drug-induced Nephrotoxicity:	0.653
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.058
A549 Cytotoxicity:	0.998	Hek293 Cytotoxicity:	1.0
BCF:	1.31 ? 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:	5.118 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.536 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.395 ? 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
NPO14000	Hopea exalata	Species	Dipterocarpaceae	Eukaryota	stem bark	Botanical Garden at Jianfeng Town, Ledong County, Hainan Province, China	2004-JUL	PMID[17190464]
NPO26194	Shorea roxburghii	Species	Dipterocarpaceae	Eukaryota	Barks	n.a.	n.a.	PMID[22209731]
NPO26194	Shorea roxburghii	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17995	Xeromphis spinosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16691	Viguiera radula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14476	Sterculia alata	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16805	Senecio cisplatinus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13778	Melandrium turkestanicum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2042	Garcinia bancana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14958	Duguetia eximia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2042	Garcinia bancana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2042	Garcinia bancana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17995	Xeromphis spinosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14000	Hopea exalata	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16805	Senecio cisplatinus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14958	Duguetia eximia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2042	Garcinia bancana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14476	Sterculia alata	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26194	Shorea roxburghii	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13778	Melandrium turkestanicum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16691	Viguiera radula	Species	Asteraceae	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	3
Inhibition	1
MIC	6

Activity Type	# Activity
Individual protein	4
Organism	6

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT462	Individual protein	Sucrase-isomaltase	Rattus norvegicus	IC50	=	55700.0	nM	PMID[22209731]
NPT68	Individual protein	Aldose reductase	Rattus norvegicus	IC50	=	29500.0	nM	PMID[22209731]
NPT671	Individual protein	Acidic alpha-glucosidase	Rattus norvegicus	IC50	>	400000.0	nM	PMID[22209731]
NPT671	Individual protein	Acidic alpha-glucosidase	Rattus norvegicus	Inhibition	=	44.0	%	PMID[22209731]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT962	Organism	Alternaria alternata	Alternaria alternata	MIC	=	1.56	ug.mL-1	PMID[17190464]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	MIC	=	11.5	ug.mL-1	PMID[17190464]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	MIC	>	50.0	ug.mL-1	PMID[17190464]
NPT1199	Organism	Valsa mali	Valsa mali	MIC	>	50.0	ug.mL-1	PMID[17190464]
NPT2705	Organism	Alternaria solani	Alternaria solani	MIC	>	50.0	ug.mL-1	PMID[17190464]
NPT2637	Organism	Colletotrichum lagenarium	Colletotrichum lagenarium	MIC	>	50.0	ug.mL-1	PMID[17190464]

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 NPC177172 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	32343
0.1-0.2	16145
0.2-0.3	1258
0.3-0.4	62
0.4-0.5	23
0.5-0.6	10
0.6-0.7	0
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC122980
1.0	High Similarity	NPC148516
1.0	High Similarity	NPC107862
0.9206	High Similarity	NPC180605
0.9104	High Similarity	NPC105073
0.9104	High Similarity	NPC224528
0.8143	Intermediate Similarity	NPC233886
0.7941	Intermediate Similarity	NPC218801
0.7937	Intermediate Similarity	NPC157081
0.7059	Intermediate Similarity	NPC242774
0.7059	Intermediate Similarity	NPC231712
0.7059	Intermediate Similarity	NPC224921
0.7059	Intermediate Similarity	NPC237546
0.5811	Remote Similarity	NPC488747
0.56	Remote Similarity	NPC174787
0.56	Remote Similarity	NPC120633
0.56	Remote Similarity	NPC213607
0.5342	Remote Similarity	NPC473665
0.5325	Remote Similarity	NPC473018
0.5185	Remote Similarity	NPC261896
0.5156	Remote Similarity	NPC176804
0.5156	Remote Similarity	NPC71686
0.5053	Remote Similarity	NPC48880

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC177172 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6804
0.1-0.2	2315
0.2-0.3	28
0.3-0.4	3
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