NPASS Compound

Natural Product: NPC322148

Natural Product ID	NPC322148
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Sacrotride A
IUPAC Name	(1S,2R,3R,4S)-5-[(2S)-2-hydroxy-3-(10-methylhexadecoxy)propoxy]cyclopentane-1,2,3,4-tetrol
Synonyms	Sacrotride A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL491880
PubChem CID	10412035
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000175] Glycerolipids [CHEMONTID:0002391] Glycerol ethers

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 82 82 0 0 0 0 0 0 0 0999 V2000 -6.1052 4.2687 -0.0743 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3303 3.5395 -0.5883 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6276 2.2882 0.1724 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4595 1.2782 0.1062 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1734 0.8822 -1.2756 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0607 -0.0403 -1.5068 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0894 -1.4150 -1.0180 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1711 -1.6639 0.4341 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1360 -1.0961 1.3221 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7250 -1.5496 1.1302 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5630 -3.0214 1.3375 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1147 -3.3972 1.1009 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1609 -2.6872 2.0352 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2371 -3.1400 1.7519 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6490 -2.8559 0.3479 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6093 -1.3966 -0.0179 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4214 -0.6296 0.7656 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7415 -0.9727 0.7271 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3471 -0.8788 -0.6415 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1897 0.4543 -1.3008 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8315 1.5129 -0.7779 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1805 1.5685 -0.7268 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6374 1.8537 0.6851 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8707 0.7116 1.4380 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9199 2.6840 0.5661 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1669 2.8112 -0.9211 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7491 2.7881 -1.4487 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1354 3.9626 -1.0915 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8422 1.7191 -1.4287 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6823 3.9669 1.0603 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6862 -1.2375 -0.6342 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0973 -2.3040 -1.7704 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2124 4.5569 0.9823 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2041 3.6342 -0.1916 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0263 5.2205 -0.6520 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3169 3.3966 -1.6670 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1934 4.2370 -0.3817 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7638 2.5195 1.2421 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5176 1.8222 -0.2585 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7927 0.4631 0.7456 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5636 1.7686 0.5495 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1116 0.3437 -1.6662 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1064 1.7965 -1.9639 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7520 -0.0160 -2.6266 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1347 0.4970 -1.0372 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1119 -1.8819 -1.4090 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1136 -2.8458 0.5572 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1825 -1.5075 0.8217 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1195 0.0200 1.1909 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4293 -1.3072 2.3970 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2341 -1.2292 0.2116 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1058 -1.0628 1.9713 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1658 -3.6095 0.6388 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8032 -3.3003 2.4074 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9162 -3.0919 0.0364 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0497 -4.4861 1.1889 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4444 -2.9452 3.1022 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1839 -1.5950 1.9426 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2488 -4.2574 1.9096 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9413 -2.6723 2.4902 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6832 -3.2702 0.1570 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0110 -3.4038 -0.3797 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8224 -1.3451 -1.1148 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5528 -1.0362 0.1688 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9530 -2.0145 1.0986 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3480 -0.3135 1.3902 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7989 -1.6093 -1.3267 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3713 0.2855 -2.3901 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0777 0.6862 -1.2474 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7475 0.7133 -1.1176 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8477 2.4697 1.1635 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6553 0.2238 1.1223 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7678 2.1771 1.0712 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6617 3.7747 -1.1624 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8175 2.6162 -2.5426 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7882 4.7039 -1.0349 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9671 1.0325 -0.7357 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3806 4.6014 0.7596 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7757 -2.0380 -0.0433 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1812 -3.3408 -1.4617 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4696 -2.2925 -2.8480 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0942 -1.8804 -1.8161 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 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 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 25 30 1 0 19 31 1 0 7 32 1 0 27 22 1 0 1 33 1 0 1 34 1 0 1 35 1 0 2 36 1 0 2 37 1 0 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 6 44 1 0 6 45 1 0 7 46 1 0 8 47 1 0 8 48 1 0 9 49 1 0 9 50 1 0 10 51 1 0 10 52 1 0 11 53 1 0 11 54 1 0 12 55 1 0 12 56 1 0 13 57 1 0 13 58 1 0 14 59 1 0 14 60 1 0 15 61 1 0 15 62 1 0 16 63 1 0 16 64 1 0 18 65 1 0 18 66 1 0 19 67 1 6 20 68 1 0 20 69 1 0 22 70 1 0 23 71 1 1 24 72 1 0 25 73 1 1 26 74 1 1 27 75 1 6 28 76 1 0 29 77 1 0 30 78 1 0 31 79 1 0 32 80 1 0 32 81 1 0 32 82 1 0 M END

Standard InCHIKey	PBKNPWUTVIEHAJ-PUZAKDQTSA-N
Standard InCHI	InChI=1S/C25H50O7/c1-3-4-5-11-14-19(2)15-12-9-7-6-8-10-13-16-31-17-20(26)18-32-25-23(29)21(27)22(28)24(25)30/h19-30H,3-18H2,1-2H3/t19?,20-,21+,22+,23-,24-/m0/s1
SMILES	CCCCCCC(CCCCCCCCCOC[C@@H](COC1[C@@H](O)[C@@H]([C@H]([C@@H]1O)O)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	462.36	Volume:	493.931 ? Van der Waals volume.
Dense:	0.936	LogP:	4.269 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.418 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.26 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	20.0	Rigid Bonds:	5.0
TPSA:	119.61 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	5.0	Rings:	1.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.176	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.913	Fsp³:	1.0
MCE-18:	22.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.608	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.348	Promiscuous compounds:	0.003

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.417	MDCK Permeability:	-4.787
Pgp-inhibitor:	0.0	Pgp-substrate:	0.563
PAMPA:	0.414 ? 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):	0.607
20% Bioavailability (F20%):	0.741	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	0.924

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118	MRP1:	0.197
Plasma Protein Binding (PPB):	94.465%	Volume Distribution (VD):	0.145
Fu:	5.953% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.898
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.834
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.701 ? 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):

2.25

Half-life (T1/2):

1.255

ADMET: Toxicity

hERG Blockers:	0.29	hERG Blockers (10um):	0.747
Human Hepatotoxicity (H-HT):	0.3	Drug-induced Liver Injury (DILI):	0.027
AMES Toxicity:	0.1	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.047	Skin Sensitization:	0.999
Carcinogencity:	0.098	Eye Corrosion:	0.136
Eye Irritation:	0.906	Respiratory Toxicity:	0.587
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.843
Hematotoxicity:	0.06	Drug-induced Nephrotoxicity:	0.852
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.103
A549 Cytotoxicity:	0.555	Hek293 Cytotoxicity:	0.148
BCF:	1.996 ? 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:	5.106 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.953 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.165 ? 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
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	(15-25 m depth) off Komun Island, Korea	1995-JUL	PMID[10217707]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346968]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170665]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754614]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	Indonesia	1996	PMID[18327911]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18942825]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	Eukaryota	n.a.	Tongan	n.a.	PMID[19877653]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	Miyako sea-knoll, southwestern Japan (2525.64' N, 12542.48' E), at a depth of 415 m	2009-OCT	PMID[21534590]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22129061]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	American Samoa	n.a.	PMID[23368996]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26821210]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30371079]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917297]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	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
ED50	5
Inhibition	3
IC50	5

Activity Type	# Activity
Cell line	8
Organism	4
Non-molecular	1

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
NPT81	Cell line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[10346968]
NPT146	Cell line	SK-OV-3	Homo sapiens	ED50	=	9.5	ug ml-1	PMID[10346968]
NPT147	Cell line	SK-MEL-2	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[10346968]
NPT574	Cell line	XF498	Homo sapiens	ED50	=	9.8	ug ml-1	PMID[10346968]
NPT148	Cell line	HCT-15	Homo sapiens	ED50	=	9.4	ug ml-1	PMID[10346968]
NPT139	Cell line	HT-29	Homo sapiens	IC50	>	2.5	ug.mL-1	PMID[22129061]
NPT400	Cell line	MDA-MB-435	Homo sapiens	IC50	>	2.5	ug.mL-1	PMID[22129061]
NPT466	Cell line	U-937	Homo sapiens	IC50	>	2.5	ug.mL-1	PMID[22129061]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	2.5	ug.mL-1	PMID[22129061]
NPT6068	Organism	Simian virus 40	Simian virus 40	Inhibition	=	90.0	%	PMID[10346968]
NPT6068	Organism	Simian virus 40	Simian virus 40	Inhibition	=	68.0	%	PMID[10346968]
NPT6068	Organism	Simian virus 40	Simian virus 40	Inhibition	=	37.0	%	PMID[10346968]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	>	10.0	ug.mL-1	PMID[22129061]

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 NPC322148 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	21956
0.1-0.2	26901
0.2-0.3	957
0.3-0.4	38
0.4-0.5	3
0.5-0.6	1
0.6-0.7	1
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
0.8462	Intermediate Similarity	NPC606258
0.6731	Remote Similarity	NPC489848
0.5172	Remote Similarity	NPC611480

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC322148 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6277
0.1-0.2	2792
0.2-0.3	77
0.3-0.4	4
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