NPASS Compound

Natural Product: NPC11685

Natural Product ID	NPC11685
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HROADJGQUKVYRU-YFNVFCEMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL366219
PubChem CID	11297045
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002967] Hexacarboxylic acids and derivatives

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 93 97 0 0 0 0 0 0 0 0999 V2000 -1.4772 -2.9022 -4.3350 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8765 -2.6767 -2.9725 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3752 -2.6649 -2.9007 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6104 -2.4940 -1.8690 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4028 -2.2484 -0.5429 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0041 -0.9129 -0.0448 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3058 -0.4718 -0.6017 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3704 0.9401 -0.3891 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5732 1.8212 -1.4302 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7111 1.3343 -2.5777 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6192 3.2529 -1.1689 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8637 4.1523 -2.2119 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9012 5.5103 -1.9827 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6952 5.9990 -0.7070 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4512 5.1450 0.3473 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4225 3.7897 0.0710 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4733 -1.1901 0.0252 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6562 -0.7077 -0.5295 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5150 -1.4344 -1.3475 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1826 -2.6190 -1.5957 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7438 -0.8436 -1.8897 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1173 0.4355 -1.6310 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3018 0.9061 -2.1918 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0915 0.1067 -2.9945 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7114 -1.1908 -3.2560 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5297 -1.6436 -2.6901 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4256 -1.2612 1.5070 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0877 -1.9640 1.8747 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8307 -0.8632 1.4919 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1208 0.3291 1.8052 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1410 0.0435 2.2119 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3018 -0.2115 3.7081 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1890 1.0876 1.9133 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1233 -0.7931 2.2309 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2916 -0.2641 1.4202 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6681 0.8865 0.6133 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0039 0.1477 -0.5200 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1045 -0.5020 -1.1858 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4869 -0.2206 -2.4679 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8344 0.6591 -3.0983 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6349 -0.9526 -3.0495 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7036 1.6958 0.0632 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6606 3.0453 0.3636 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7333 3.5206 1.0970 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6659 4.0212 -0.1323 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5584 -2.0588 2.9206 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0568 0.1792 3.2731 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1256 -2.2569 3.2642 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1253 -3.5445 3.7402 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0910 -4.4980 2.9405 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1657 -3.7793 5.1945 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8006 -2.4312 -5.0781 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4689 -2.4326 -4.3587 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4969 -4.0011 -4.5097 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2669 -2.6916 0.0135 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5714 -3.0269 -0.2962 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3677 -0.5817 -1.6781 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0248 3.7394 -3.2193 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0906 6.2158 -2.7881 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7207 7.0559 -0.5072 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2957 5.5680 1.3279 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2260 3.1022 0.8814 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3815 -2.2612 -0.3352 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4871 1.0471 -1.0008 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6181 1.9270 -1.9969 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0238 0.4541 -3.4447 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3216 -1.8265 -3.8832 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2531 -2.6715 -2.9129 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2809 -1.8099 1.8854 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0200 -2.9179 1.3867 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8953 0.6239 4.2104 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3904 -0.2414 4.2811 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0015 -1.0857 3.8680 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8104 2.0559 2.2835 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0569 0.8669 2.6233 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6464 1.0857 0.9442 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7379 -0.9872 0.7380 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0475 0.2304 2.0758 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9790 1.4939 1.2096 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6101 0.8446 -1.2447 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4544 -2.0470 -3.0605 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4993 -0.8025 -2.3492 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9515 -0.5578 -4.0246 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1901 5.0075 -0.2733 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4942 4.0457 0.5987 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0582 3.6448 -1.0906 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6935 -2.0258 2.9551 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3368 -2.9783 2.3902 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2888 -2.0449 4.0021 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8980 0.1317 3.7664 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4002 -2.8666 5.7748 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9220 -4.5348 5.4883 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8060 -4.1544 5.5847 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 6 5 1 6 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 7 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 17 27 1 0 27 28 1 0 28 29 1 0 29 30 1 6 30 31 1 0 31 32 1 0 31 33 1 0 29 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 36 42 1 0 42 43 1 0 43 44 2 0 43 45 1 0 34 46 1 0 34 47 1 1 28 48 1 0 48 49 1 0 49 50 2 0 49 51 1 0 37 6 1 0 29 6 1 0 16 11 1 0 26 21 1 0 31 27 1 0 1 52 1 0 1 53 1 0 1 54 1 0 5 55 1 0 5 56 1 0 7 57 1 6 12 58 1 0 13 59 1 0 14 60 1 0 15 61 1 0 16 62 1 0 17 63 1 6 22 64 1 0 23 65 1 0 24 66 1 0 25 67 1 0 26 68 1 0 27 69 1 1 28 70 1 6 32 71 1 0 32 72 1 0 32 73 1 0 33 74 1 0 33 75 1 0 33 76 1 0 35 77 1 0 35 78 1 0 36 79 1 1 37 80 1 6 41 81 1 0 41 82 1 0 41 83 1 0 45 84 1 0 45 85 1 0 45 86 1 0 46 87 1 0 46 88 1 0 46 89 1 0 47 90 1 0 51 91 1 0 51 92 1 0 51 93 1 0 M END

Standard InCHIKey	HROADJGQUKVYRU-YFNVFCEMSA-N
Standard InCHI	InChI=1S/C37H42O14/c1-20(38)45-19-36-29(47-22(3)40)26(46-21(2)39)18-35(7,44)37(36)30(48-23(4)41)27(34(5,6)51-37)28(49-32(42)24-14-10-8-11-15-24)31(36)50-33(43)25-16-12-9-13-17-25/h8-17,26-31,44H,18-19H2,1-7H3/t26-,27+,28-,29-,30+,31-,35-,36-,37-/m0/s1
SMILES	CC(=O)OC[C@@]12[C@@H](OC(=O)c3ccccc3)[C@@H](OC(=O)c3ccccc3)[C@@H]3[C@H]([C@]2(OC3(C)C)[C@@](C[C@@H]([C@@H]1OC(=O)C)OC(=O)C)(C)O)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	710.26	Volume:	697.151 ? Van der Waals volume.
Dense:	1.019	LogP:	2.852 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.894 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.649 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	32.0
TPSA:	187.26 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.295	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.015	Fsp³:	0.514
MCE-18:	180.107 ? 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:	0.329	Fluc inhibitor:	0.018 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.199 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.085	Promiscuous compounds:	0.097

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.25	MDCK Permeability:	-4.634
Pgp-inhibitor:	1.0	Pgp-substrate:	0.373
PAMPA:	0.297 ? 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%):	0.016	30% Bioavailability (F30%):	0.36
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.18	MRP1:	1.0
Plasma Protein Binding (PPB):	77.755%	Volume Distribution (VD):	-0.416
Fu:	20.327% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.988	BCRP inhibitor:	0.002
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.212
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.008	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.999 ? 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):

1.664

Half-life (T1/2):

1.289

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.245
Human Hepatotoxicity (H-HT):	0.094	Drug-induced Liver Injury (DILI):	0.633
AMES Toxicity:	0.81	Rat Oral Acute Toxicity:	0.202
Maximum Recommended Daily Dose:	0.165	Skin Sensitization:	0.995
Carcinogencity:	0.738	Eye Corrosion:	0.001
Eye Irritation:	0.213	Respiratory Toxicity:	0.019
Drug-induced Neurotoxicity:	0.282	Ototoxicity:	0.235
Hematotoxicity:	0.148	Drug-induced Nephrotoxicity:	0.723
Genotoxicity:	0.616	RPMI-8226 Immunitoxicity:	0.045
A549 Cytotoxicity:	0.179	Hek293 Cytotoxicity:	0.417
BCF:	0.615 ? 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:	3.651 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.361 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.822 ? 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
NPO33107	zinowiewia costaricensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974580]
NPO33107	zinowiewia costaricensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
Ki	1
Reversal ability	6
Activity	5
Intrinsic Toxicity	6

Activity Type	# Activity
Cell line	14
Others	4

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
NPT886	Cell line	NIH3T3	Mus musculus	Ki	=	1737.0	nM	DrugMatrix in vitro pharmacology data
NPT886	Cell line	NIH3T3	Mus musculus	Reversal ability	=	11.13	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Reversal ability	=	10.78	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Reversal ability	=	4.26	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Reversal ability	=	233.6	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Reversal ability	=	102.17	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Reversal ability	=	6.23	n.a.	PMID[15974580]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[25218909]
NPT886	Cell line	NIH3T3	Mus musculus	Intrinsic Toxicity	=	4.26	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Intrinsic Toxicity	=	233.6	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Intrinsic Toxicity	=	102.17	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Intrinsic Toxicity	=	6.23	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Intrinsic Toxicity	=	11.13	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Intrinsic Toxicity	=	10.78	n.a.	PMID[15974580]
NPT2	Others	Unspecified	n.a.	Activity	=	0.0	%	PMID[21182258]
NPT2	Others	Unspecified	n.a.	Activity	=	27.1	%	PMID[17894480]
NPT2	Others	Unspecified	n.a.	Activity	=	72.6	%	PMID[9207950]
NPT2	Others	Unspecified	n.a.	Activity	=	92.1	%	PMID[20392109]

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 NPC11685 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	12280
0.1-0.2	35077
0.2-0.3	1764
0.3-0.4	535
0.4-0.5	121
0.5-0.6	48
0.6-0.7	22
0.7-0.8	0
0.8-0.85	1
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC16912
0.8788	High Similarity	NPC472569
0.8788	High Similarity	NPC472570
0.8676	High Similarity	NPC481489
0.8286	Intermediate Similarity	NPC481488
0.7761	Intermediate Similarity	NPC281717
0.7681	Intermediate Similarity	NPC471104
0.7361	Intermediate Similarity	NPC97667
0.7123	Intermediate Similarity	NPC95265
0.7027	Intermediate Similarity	NPC282239
0.6986	Remote Similarity	NPC57628
0.6901	Remote Similarity	NPC147880
0.6892	Remote Similarity	NPC70716
0.68	Remote Similarity	NPC472568
0.6761	Remote Similarity	NPC483886
0.6753	Remote Similarity	NPC488917
0.6711	Remote Similarity	NPC479042
0.6623	Remote Similarity	NPC481486
0.6579	Remote Similarity	NPC471102
0.6575	Remote Similarity	NPC148062
0.65	Remote Similarity	NPC610134
0.6364	Remote Similarity	NPC481490
0.6351	Remote Similarity	NPC147217
0.6351	Remote Similarity	NPC137718
0.6301	Remote Similarity	NPC51314
0.6118	Remote Similarity	NPC294512
0.6104	Remote Similarity	NPC479043
0.6104	Remote Similarity	NPC252314
0.6081	Remote Similarity	NPC473060
0.6047	Remote Similarity	NPC483868
0.6026	Remote Similarity	NPC106895
0.6	Remote Similarity	NPC483845
0.5844	Remote Similarity	NPC473088
0.5802	Remote Similarity	NPC481487
0.5747	Remote Similarity	NPC176413
0.5747	Remote Similarity	NPC483885
0.5747	Remote Similarity	NPC479045
0.5714	Remote Similarity	NPC472572
0.5663	Remote Similarity	NPC479040
0.5658	Remote Similarity	NPC483902
0.5658	Remote Similarity	NPC472577
0.5641	Remote Similarity	NPC171207
0.5584	Remote Similarity	NPC90257
0.5584	Remote Similarity	NPC69357
0.5513	Remote Similarity	NPC471101
0.5488	Remote Similarity	NPC481064
0.5488	Remote Similarity	NPC483849
0.5465	Remote Similarity	NPC180668
0.5465	Remote Similarity	NPC10904
0.5455	Remote Similarity	NPC30171
0.5385	Remote Similarity	NPC163719
0.5385	Remote Similarity	NPC479047
0.5385	Remote Similarity	NPC291638
0.5385	Remote Similarity	NPC200471
0.5385	Remote Similarity	NPC95810
0.5385	Remote Similarity	NPC472575
0.5375	Remote Similarity	NPC483844
0.5325	Remote Similarity	NPC241951
0.5263	Remote Similarity	NPC481047
0.5263	Remote Similarity	NPC481045
0.525	Remote Similarity	NPC471100
0.525	Remote Similarity	NPC605884
0.5244	Remote Similarity	NPC96903
0.519	Remote Similarity	NPC4341
0.5185	Remote Similarity	NPC479044
0.5181	Remote Similarity	NPC483848
0.5181	Remote Similarity	NPC51602
0.5176	Remote Similarity	NPC6815
0.5128	Remote Similarity	NPC483879
0.5119	Remote Similarity	NPC294803
0.5119	Remote Similarity	NPC481062
0.5119	Remote Similarity	NPC481058
0.5119	Remote Similarity	NPC481060
0.5065	Remote Similarity	NPC475429
0.5065	Remote Similarity	NPC211137
0.5062	Remote Similarity	NPC254558
0.5062	Remote Similarity	NPC471107
0.5057	Remote Similarity	NPC125106
0.5057	Remote Similarity	NPC472573
0.5053	Remote Similarity	NPC6981

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC11685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3543
0.1-0.2	5433
0.2-0.3	171
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