NPASS Compound

Natural Product: NPC575037

Natural Product ID	NPC575037
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2R,3R,4S,5S,6R)-2-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18S,19S)-16-hydroxy-5'-(hydroxymethyl)-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-19-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
IUPAC Name	(2~{R},3~{R},4~{S},5~{S},6~{R})-2-[(1~{R},2~{S},4~{S},5'~{R},6~{R},7~{S},8~{R},9~{S},12~{S},13~{R},16~{S},18~{S},19~{S})-16-hydroxy-5'-(hydroxymethyl)-7,9,13-trimethyl-spiro[5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-tetrahydropyran]-19-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic 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 97103 0 0 0 0 0 0 0 0999 V2000 4.7196 0.9746 -2.2643 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9404 0.8194 -1.0068 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3426 -0.5680 -0.8401 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3416 -0.6929 0.6804 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8762 -0.3539 1.0107 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2264 -1.1448 -0.0331 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2132 -1.0506 -0.2482 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0562 -1.1016 1.0033 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5043 -0.9993 0.4979 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3734 -0.6790 1.5012 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9831 0.5297 1.2087 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6842 1.5185 2.1429 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1315 2.7236 1.6027 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5467 3.9244 2.3120 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1613 3.8998 2.2105 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6415 2.7587 1.5990 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1489 3.1667 0.3717 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2078 1.3874 1.9049 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9612 1.0269 3.2278 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4804 0.3806 1.0352 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8813 0.6242 -0.2839 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7744 -2.3332 -0.1560 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2177 -2.6480 -0.3144 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3460 -4.0652 -0.8259 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2091 -4.1599 -1.9121 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0042 -4.6666 -1.1814 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1908 -3.7464 -2.0589 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9953 -2.3817 -1.4333 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4828 -1.3608 -2.4400 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5420 -2.1736 -1.2103 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2097 -1.9758 -2.4851 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6673 -1.7290 -2.3231 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9401 -0.6805 -1.3032 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4149 0.6324 -1.8017 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2248 0.1890 1.1896 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8580 0.8840 0.1936 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9465 2.3395 0.6377 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7157 2.3379 1.9443 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0998 1.7803 1.6222 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0353 2.9958 1.5944 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0227 3.6348 2.8430 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1590 1.1416 0.2744 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0949 0.3308 -0.0294 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5909 2.0034 -2.6915 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4310 0.2725 -3.0700 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8176 0.8284 -2.1104 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1742 1.6223 -0.8455 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0396 -1.2933 -1.3033 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5115 -1.7552 0.9483 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6535 -0.7902 2.0173 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7143 0.7207 0.9612 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -2.2239 0.0856 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4995 -0.0879 -0.7653 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8929 -2.0947 1.4626 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7764 -0.2571 1.6313 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4846 -0.2358 -0.3101 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5922 0.8942 0.2408 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8143 2.8102 0.5327 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8874 4.8191 1.7422 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8929 4.0473 3.3378 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7049 3.8729 3.0916 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0294 3.4512 2.3742 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0573 2.8139 0.1977 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2764 1.3231 1.6314 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5412 0.2398 3.4231 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8587 -0.6081 1.3048 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3190 1.2859 -0.7405 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3318 -3.1064 0.5221 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6743 -2.6086 0.7184 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7842 -1.9279 -0.9144 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7746 -4.7338 -0.0263 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1198 -4.2690 -1.5672 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2083 -5.5793 -1.7787 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4446 -5.0053 -0.2864 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7051 -3.6955 -3.0359 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2215 -4.2601 -2.2450 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2490 -1.7675 -3.4602 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0068 -0.3694 -2.3021 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5851 -1.2342 -2.4195 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1363 -3.1142 -0.7350 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3078 -1.2162 -3.1338 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1035 -2.9362 -3.0719 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1667 -2.6995 -2.1317 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0654 -1.3766 -3.3059 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4956 0.5224 -2.4363 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1895 1.0246 -2.5258 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1607 1.3525 -1.0200 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4411 2.9489 -0.1366 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9060 2.6737 0.8078 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1655 1.6999 2.6561 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7666 3.3651 2.3511 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3910 1.0948 2.4393 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0720 2.7114 1.3685 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6889 3.7415 0.8617 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6333 3.2085 3.4738 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2813 1.9062 -0.5208 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0800 0.5021 0.2516 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 13 16 1 0 16 17 1 0 16 18 1 0 18 19 1 0 18 20 1 0 20 21 1 0 9 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 6 4 35 1 0 36 35 1 1 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 42 43 1 0 36 2 1 0 33 3 1 0 43 36 1 0 33 6 1 0 30 7 1 0 20 11 1 0 28 22 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 1 3 48 1 6 4 49 1 6 5 50 1 0 5 51 1 0 6 52 1 1 7 53 1 6 8 54 1 0 8 55 1 0 9 56 1 6 11 57 1 6 13 58 1 6 14 59 1 0 14 60 1 0 15 61 1 0 16 62 1 1 17 63 1 0 18 64 1 6 19 65 1 0 20 66 1 1 21 67 1 0 22 68 1 1 23 69 1 0 23 70 1 0 24 71 1 1 25 72 1 0 26 73 1 0 26 74 1 0 27 75 1 0 27 76 1 0 29 77 1 0 29 78 1 0 29 79 1 0 30 80 1 1 31 81 1 0 31 82 1 0 32 83 1 0 32 84 1 0 34 85 1 0 34 86 1 0 34 87 1 0 37 88 1 0 37 89 1 0 38 90 1 0 38 91 1 0 39 92 1 1 40 93 1 0 40 94 1 0 41 95 1 0 42 96 1 0 42 97 1 0 M END

Standard InCHIKey	ZAHQALYVTUETNX-UFOCHEJFSA-N
Standard InCHI	InChI=1S/C33H54O10/c1-16-26-24(43-33(16)9-4-17(13-34)15-40-33)12-21-19-11-23(41-30-29(39)28(38)27(37)25(14-35)42-30)22-10-18(36)5-7-31(22,2)20(19)6-8-32(21,26)3/h16-30,34-39H,4-15H2,1-3H3/t16-,17+,18-,19+,20-,21-,22+,23-,24-,25+,26-,27+,28-,29+,30+,31+,32-,33+/m0/s1
SMILES	C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4C[C@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@H]5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]23C)O[C@]12CC[C@H](CO)CO2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.37	Volume:	607.331 ? Van der Waals volume.
Dense:	1.005	LogP:	1.572 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.163 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.787 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	36.0
TPSA:	158.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	6.0	Rings:	7.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.258	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.95	Fsp³:	1.0
MCE-18:	173.182 ? 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:	0.71	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.038 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.201	Promiscuous compounds:	0.021

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.781	MDCK Permeability:	-5.215
Pgp-inhibitor:	0.01	Pgp-substrate:	0.702
PAMPA:	0.882 ? 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):	0.001
20% Bioavailability (F20%):	0.038	30% Bioavailability (F30%):	0.496
50% Bioavailability (F50%):	0.871

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018	MRP1:	0.087
Plasma Protein Binding (PPB):	56.225%	Volume Distribution (VD):	-0.455
Fu:	39.203% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.197
BSEP inhibitor:	0.142

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.775
HLM stability:	0.013 ? 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):

3.902

Half-life (T1/2):

2.663

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.049
Human Hepatotoxicity (H-HT):	0.721	Drug-induced Liver Injury (DILI):	0.889
AMES Toxicity:	0.945	Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.089	Skin Sensitization:	1.0
Carcinogencity:	0.635	Eye Corrosion:	0.0
Eye Irritation:	0.039	Respiratory Toxicity:	0.028
Drug-induced Neurotoxicity:	0.011	Ototoxicity:	0.988
Hematotoxicity:	0.114	Drug-induced Nephrotoxicity:	0.925
Genotoxicity:	0.038	RPMI-8226 Immunitoxicity:	0.178
A549 Cytotoxicity:	0.925	Hek293 Cytotoxicity:	0.81
BCF:	1.37 ? 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:	3.279 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.379 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.856 ? 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
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11830167]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18141	Solanum torvum	Species	Solanaceae	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 NPC575037 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	25612
0.1-0.2	20967
0.2-0.3	2848
0.3-0.4	273
0.4-0.5	100
0.5-0.6	41
0.6-0.7	8
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
0.9014	High Similarity	NPC277715
0.7867	Intermediate Similarity	NPC144790
0.7867	Intermediate Similarity	NPC149400
0.7179	Intermediate Similarity	NPC88962
0.7024	Intermediate Similarity	NPC131693
0.7024	Intermediate Similarity	NPC475436
0.6867	Remote Similarity	NPC485594
0.6452	Remote Similarity	NPC485605
0.6437	Remote Similarity	NPC485591
0.6404	Remote Similarity	NPC121453
0.6316	Remote Similarity	NPC485603
0.6292	Remote Similarity	NPC312678
0.6292	Remote Similarity	NPC253268
0.6235	Remote Similarity	NPC24960
0.5889	Remote Similarity	NPC179859
0.5889	Remote Similarity	NPC473851
0.5843	Remote Similarity	NPC181845
0.5714	Remote Similarity	NPC296734
0.5604	Remote Similarity	NPC297348
0.5604	Remote Similarity	NPC325828
0.5604	Remote Similarity	NPC249204
0.5604	Remote Similarity	NPC48339
0.5604	Remote Similarity	NPC141769
0.5604	Remote Similarity	NPC477547
0.5584	Remote Similarity	NPC248944
0.5584	Remote Similarity	NPC7479
0.5584	Remote Similarity	NPC257296
0.5543	Remote Similarity	NPC294686
0.5543	Remote Similarity	NPC234352
0.5393	Remote Similarity	NPC473774
0.5393	Remote Similarity	NPC481419
0.5393	Remote Similarity	NPC481417
0.5368	Remote Similarity	NPC206003
0.5368	Remote Similarity	NPC473610
0.5357	Remote Similarity	NPC486119
0.5333	Remote Similarity	NPC475550
0.5319	Remote Similarity	NPC477451
0.5312	Remote Similarity	NPC211354
0.5312	Remote Similarity	NPC107188
0.5263	Remote Similarity	NPC222731
0.5208	Remote Similarity	NPC291547
0.5208	Remote Similarity	NPC485593
0.5208	Remote Similarity	NPC174024
0.5204	Remote Similarity	NPC107962
0.5152	Remote Similarity	NPC6295
0.5146	Remote Similarity	NPC248746
0.51	Remote Similarity	NPC195297
0.5055	Remote Similarity	NPC481420
0.5055	Remote Similarity	NPC481421
0.505	Remote Similarity	NPC113044
0.505	Remote Similarity	NPC283829
0.505	Remote Similarity	NPC485599
0.505	Remote Similarity	NPC160426
0.505	Remote Similarity	NPC161676
0.5048	Remote Similarity	NPC485604

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC575037 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7509
0.1-0.2	1553
0.2-0.3	81
0.3-0.4	4
0.4-0.5	1
0.5-0.6	2
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
0.5604	Remote Similarity	NPD8171	Phase 2
0.5584	Remote Similarity	NPD6928	Phase 2

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