NPASS Compound

Natural Product: NPC471102

Natural Product ID	NPC471102
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UNXHKUBBGHPHHO-IOVHKGPRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2373415
PubChem CID	10652508
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic 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 98 0 0 0 0 0 0 0 0999 V2000 -2.6776 -2.5491 3.0651 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4702 -1.8597 2.5080 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 -1.5246 3.2851 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3486 -1.5817 1.1681 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2101 -0.9410 0.6983 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1768 -0.6856 -0.7694 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1330 0.0110 -1.0655 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1636 1.2755 -0.4487 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2497 2.4887 -1.1155 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3071 2.4422 -2.3708 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2740 3.7693 -0.4088 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2134 3.8636 0.9640 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2385 5.0978 1.6090 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3245 6.2622 0.8964 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3859 6.1815 -0.4795 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3604 4.9491 -1.1133 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3358 -0.8253 -0.7102 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7523 -0.3827 0.5756 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9233 0.3176 0.8121 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6389 0.5606 -0.1910 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3531 0.7694 2.1079 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6384 0.5537 3.2688 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1144 1.0169 4.4754 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3130 1.7107 4.5864 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0251 1.9271 3.4389 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5398 1.4600 2.2406 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2030 -2.2865 -0.7998 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9612 -2.8531 -1.3823 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1510 -1.8796 -1.6574 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1888 -1.3310 -2.9223 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8937 -1.3141 -3.7278 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0882 -1.4956 -2.8223 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2901 -0.2593 -2.0721 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2973 0.3959 -2.2259 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2925 0.2449 -1.1043 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0736 0.5730 0.0641 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3085 1.8749 0.4723 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8263 2.8196 -0.1982 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0934 2.2014 1.6499 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6620 1.2151 2.4490 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3982 1.5787 3.5560 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5937 2.9036 3.9043 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0285 3.8601 3.1090 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2925 3.5062 2.0028 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4890 -2.5005 -1.8177 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5256 -3.7452 -2.4296 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3070 -4.7794 -2.0116 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0504 -4.6263 -1.0135 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3400 -6.1192 -2.6787 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9242 0.0460 -4.4220 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8448 -2.3361 -4.8434 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5210 -4.0297 -0.5436 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3498 -3.4663 -2.6116 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4917 -2.5489 2.3402 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9823 -2.0346 3.9965 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3786 -3.5835 3.3060 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7161 -1.4121 1.0798 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2003 0.0721 1.2081 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1486 0.1420 -2.1890 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1453 2.9870 1.5664 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1908 5.1774 2.6987 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3430 7.2270 1.4171 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 7.1216 -1.0201 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4106 4.9267 -2.1969 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1505 -0.4755 -1.4002 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7113 0.0183 3.1905 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5755 0.8625 5.4012 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6876 2.0750 5.5357 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9624 2.4674 3.5126 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1634 1.6702 1.3628 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3988 -2.8162 0.1816 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1026 -2.6653 -1.3956 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9683 -1.8949 -3.3132 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9681 1.2279 -1.5036 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5149 0.1831 2.1852 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8424 0.7944 4.1797 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1725 3.1206 4.7712 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1636 4.9112 3.3558 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8681 4.3242 1.4102 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1615 -2.4159 -0.9335 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9208 -6.0651 -3.7043 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8409 -6.8989 -2.0852 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4031 -6.4197 -2.7842 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5545 0.7668 -3.9105 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2550 -0.0307 -5.4729 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1118 0.4875 -4.4620 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7843 -2.2516 -5.4310 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0075 -1.9965 -5.5192 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6050 -3.3484 -4.5348 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4178 -3.8779 -0.0117 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2896 -4.2493 0.2557 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4323 -4.9808 -1.1035 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1926 -3.1016 -2.9340 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 1 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 32 33 1 0 33 34 2 0 33 35 1 0 35 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 32 45 1 0 45 46 1 0 46 47 1 0 47 48 2 0 47 49 1 0 31 50 1 0 31 51 1 0 28 52 1 0 28 53 1 6 35 6 1 0 44 39 1 0 29 6 1 0 16 11 1 0 26 21 1 0 45 29 1 0 1 54 1 0 1 55 1 0 1 56 1 0 5 57 1 0 5 58 1 0 7 59 1 6 12 60 1 0 13 61 1 0 14 62 1 0 15 63 1 0 16 64 1 0 17 65 1 6 22 66 1 0 23 67 1 0 24 68 1 0 25 69 1 0 26 70 1 0 27 71 1 0 27 72 1 0 32 73 1 0 35 74 1 6 40 75 1 0 41 76 1 0 42 77 1 0 43 78 1 0 44 79 1 0 45 80 1 1 49 81 1 0 49 82 1 0 49 83 1 0 50 84 1 0 50 85 1 0 50 86 1 0 51 87 1 0 51 88 1 0 51 89 1 0 52 90 1 0 52 91 1 0 52 92 1 0 53 93 1 0 M END

Standard InCHIKey	UNXHKUBBGHPHHO-IOVHKGPRSA-N
Standard InCHI	InChI=1S/C40H40O13/c1-23(41)48-22-39-31(51-35(45)26-17-11-7-12-18-26)28(50-34(44)25-15-9-6-10-16-25)21-38(5,47)40(39)32(49-24(2)42)29(37(3,4)53-40)30(43)33(39)52-36(46)27-19-13-8-14-20-27/h6-20,28-29,31-33,47H,21-22H2,1-5H3/t28-,29?,31-,32+,33+,38-,39-,40-/m0/s1
SMILES	CC(=O)OC[C@]12[C@@H](OC(=O)c3ccccc3)[C@@H](OC(=O)c3ccccc3)C[C@]([C@@]32OC(C(C(=O)[C@H]1OC(=O)c1ccccc1)[C@H]3OC(=O)C)(C)C)(C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	728.25	Volume:	723.783 ? Van der Waals volume.
Dense:	1.006	LogP:	3.559 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.298 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.435 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	38.0
TPSA:	178.03 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.247	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.914	Fsp³:	0.4
MCE-18:	191.714 ? 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:	0.62	Fluc inhibitor:	0.007 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.562 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.072	Promiscuous compounds:	0.01

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.472	MDCK Permeability:	-4.823
Pgp-inhibitor:	0.741	Pgp-substrate:	0.004
PAMPA:	0.124 ? 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%):	0.0	30% Bioavailability (F30%):	0.001
50% Bioavailability (F50%):	0.146

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.961	MRP1:	1.0
Plasma Protein Binding (PPB):	94.067%	Volume Distribution (VD):	-0.415
Fu:	6.972% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.992
OATP1B3 inhibitor:	0.838	BCRP inhibitor:	0.0
BSEP inhibitor:	0.928

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.705
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.397
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.871	CYP3A4-substrate:	0.078
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.997 ? 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):

1.125

Half-life (T1/2):

1.434

ADMET: Toxicity

hERG Blockers:	0.035	hERG Blockers (10um):	0.414
Human Hepatotoxicity (H-HT):	0.019	Drug-induced Liver Injury (DILI):	0.976
AMES Toxicity:	0.737	Rat Oral Acute Toxicity:	0.173
Maximum Recommended Daily Dose:	0.622	Skin Sensitization:	1.0
Carcinogencity:	0.924	Eye Corrosion:	0.0
Eye Irritation:	0.573	Respiratory Toxicity:	0.028
Drug-induced Neurotoxicity:	0.894	Ototoxicity:	0.11
Hematotoxicity:	0.015	Drug-induced Nephrotoxicity:	0.816
Genotoxicity:	0.657	RPMI-8226 Immunitoxicity:	0.161
A549 Cytotoxicity:	0.493	Hek293 Cytotoxicity:	0.838
BCF:	0.705 ? 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:	3.76 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.236 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.871 ? 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
Intrinsic Toxicity	6

Activity Type	# Activity
Cell line	13

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	=	1034.0	nM	PMID[24033131]
NPT886	Cell line	NIH3T3	Mus musculus	Reversal ability	=	16.64	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Reversal ability	=	15.41	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Reversal ability	=	9.93	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Reversal ability	=	33.1	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Reversal ability	=	8.09	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Reversal ability	=	7.31	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Intrinsic Toxicity	=	16.29	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Intrinsic Toxicity	=	35.01	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Intrinsic Toxicity	=	28.93	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Intrinsic Toxicity	=	17.67	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Intrinsic Toxicity	=	38.06	n.a.	PMID[15974580]
NPT886	Cell line	NIH3T3	Mus musculus	Intrinsic Toxicity	=	29.1	n.a.	PMID[15974580]

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 NPC471102 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	11281
0.1-0.2	36017
0.2-0.3	1901
0.3-0.4	514
0.4-0.5	104
0.5-0.6	21
0.6-0.7	17
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9394	High Similarity	NPC282239
0.7027	Intermediate Similarity	NPC472569
0.6842	Remote Similarity	NPC472568
0.6842	Remote Similarity	NPC51602
0.6757	Remote Similarity	NPC254558
0.6711	Remote Similarity	NPC70716
0.6711	Remote Similarity	NPC106895
0.6579	Remote Similarity	NPC11685
0.6579	Remote Similarity	NPC16912
0.6456	Remote Similarity	NPC481488
0.6364	Remote Similarity	NPC472570
0.6316	Remote Similarity	NPC471107
0.6316	Remote Similarity	NPC471100
0.6316	Remote Similarity	NPC605884
0.6282	Remote Similarity	NPC97667
0.6163	Remote Similarity	NPC479045
0.6125	Remote Similarity	NPC481489
0.6125	Remote Similarity	NPC479042
0.6076	Remote Similarity	NPC95265
0.5974	Remote Similarity	NPC471101
0.5974	Remote Similarity	NPC483842
0.5949	Remote Similarity	NPC57628
0.5921	Remote Similarity	NPC483886
0.5696	Remote Similarity	NPC171207
0.5625	Remote Similarity	NPC471103
0.5618	Remote Similarity	NPC176413
0.5618	Remote Similarity	NPC483885
0.5581	Remote Similarity	NPC610134
0.5513	Remote Similarity	NPC281717
0.5316	Remote Similarity	NPC51314
0.5309	Remote Similarity	NPC471104
0.5294	Remote Similarity	NPC481486
0.5275	Remote Similarity	NPC294512
0.5238	Remote Similarity	NPC481490
0.5233	Remote Similarity	NPC479049
0.5217	Remote Similarity	NPC483868
0.5185	Remote Similarity	NPC137718
0.5181	Remote Similarity	NPC479043
0.5125	Remote Similarity	NPC473060
0.5119	Remote Similarity	NPC96903

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471102 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3430
0.1-0.2	5528
0.2-0.3	190
0.3-0.4	2
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