NPASS Compound

Natural Product: NPC471172

Natural Product ID	NPC471172
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YGZNSMYENXMHII-RMPCGMHFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2386299
PubChem CID	73348890
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

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 100107 0 0 0 0 0 0 0 0999 V2000 -8.1882 -2.4189 -1.3003 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9695 -1.8858 -2.0139 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8514 -1.8303 -1.0444 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0564 -2.2026 0.1352 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5859 -1.3895 -1.3638 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4908 -1.3217 -0.4727 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1355 0.1024 -0.2971 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9546 0.4134 0.6284 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3495 1.5304 -0.0221 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3880 2.8267 0.3965 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0196 3.0772 1.4546 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7530 3.9416 -0.2919 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8708 5.1462 0.2373 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2658 6.3679 -0.3731 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0105 3.8414 -1.5486 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9822 -0.7768 0.7110 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1480 -1.3896 -0.5953 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3520 -2.2035 -0.8905 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0987 -2.2800 -2.3861 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6979 -2.2790 -2.5601 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0996 -2.1309 -1.2995 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0503 -1.1287 -1.3309 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4997 -0.9947 0.1421 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4193 -0.3964 1.0013 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6778 -0.6142 2.4570 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4214 -1.4790 2.9750 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4651 -1.5783 1.8894 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -1.1718 2.6935 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6751 0.6617 3.2136 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7698 1.0194 3.7609 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3963 1.4819 3.3769 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2458 2.6682 4.1324 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9255 -2.3785 0.5248 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7332 -0.1323 0.0398 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6693 -0.8672 -0.8433 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0237 -0.2445 0.4194 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8945 -1.1606 1.1940 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6765 1.1540 0.2750 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4375 1.9976 0.4475 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5604 1.2806 -0.5541 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9996 1.3718 -1.8641 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1310 2.0835 -1.8911 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1691 1.2781 -1.0845 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3433 0.0563 -1.7763 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3342 2.0750 -1.3950 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1462 2.5535 -2.6118 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8948 2.0938 -3.0991 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6446 0.0553 -1.8747 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4578 -3.5572 -0.4042 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4838 -3.8863 0.2594 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5265 -4.5563 -0.5966 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7093 -5.8696 -0.0821 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1882 -2.1899 -0.2141 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1327 -2.0210 -1.7182 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2620 -3.5273 -1.3744 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7442 -2.5788 -2.8502 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1815 -0.8583 -2.3748 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8602 -1.7070 0.4990 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0142 0.6263 0.1381 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0028 0.6020 -1.3023 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3431 0.7504 1.5816 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4255 5.3229 1.1660 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0125 7.2115 -0.3850 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6084 6.7309 0.1961 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0333 6.2129 -1.4254 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4716 4.4670 -2.3497 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0114 4.2869 -1.3785 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0432 2.8182 -1.9606 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2806 -0.4896 -1.3227 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5706 -3.1409 -2.8561 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4702 -1.3328 -2.8199 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1903 -3.1100 -0.9670 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8985 -1.6122 -1.8505 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4563 0.7054 0.8420 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0461 -2.4934 3.2986 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8279 -1.0403 3.9096 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4167 -1.2186 2.3297 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5902 -2.6482 1.6852 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4063 -0.7862 3.4499 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1668 2.8310 4.7283 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0520 3.5354 3.4645 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6399 2.5606 4.8164 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1006 -2.9566 -0.4370 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1410 -2.9558 1.0503 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8301 -2.4532 1.1537 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9414 -0.7275 1.2757 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6188 -1.3084 2.2591 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1247 -2.1455 0.6858 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4216 1.3311 1.0747 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0299 1.7478 1.4477 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5370 3.0513 0.3598 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5671 1.6775 -0.5011 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0766 3.1341 -1.5849 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2328 -0.3287 -1.6230 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1908 2.2598 -0.7862 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8471 3.2047 -3.1629 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7824 0.0878 -2.8525 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7988 -6.0896 -0.1748 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0848 -6.5651 -0.6409 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4485 -5.8240 1.0030 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 3 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 2 0 10 12 1 0 12 13 2 0 13 14 1 0 12 15 1 0 8 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 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 6 25 29 1 0 29 30 2 0 29 31 1 0 31 32 1 0 23 33 1 1 23 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 43 45 1 0 45 46 2 0 46 47 1 0 22 48 1 0 18 49 1 1 49 50 2 0 49 51 1 0 51 52 1 0 18 6 1 0 40 34 1 0 47 42 1 0 16 27 1 1 36 34 1 0 43 38 1 0 24 16 1 0 21 17 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 0 2 57 1 0 6 58 1 1 7 59 1 0 7 60 1 0 8 61 1 1 13 62 1 0 14 63 1 0 14 64 1 0 14 65 1 0 15 66 1 0 15 67 1 0 15 68 1 0 17 69 1 6 19 70 1 0 19 71 1 0 21 72 1 1 22 73 1 6 24 74 1 0 26 75 1 0 26 76 1 0 27 77 1 0 27 78 1 0 28 79 1 0 32 80 1 0 32 81 1 0 32 82 1 0 33 83 1 0 33 84 1 0 33 85 1 0 37 86 1 0 37 87 1 0 37 88 1 0 38 89 1 0 39 90 1 0 39 91 1 0 40 92 1 6 42 93 1 1 44 94 1 0 45 95 1 0 46 96 1 0 48 97 1 0 52 98 1 0 52 99 1 0 52100 1 0 M END

Standard InCHIKey	YGZNSMYENXMHII-RMPCGMHFSA-N
Standard InCHI	InChI=1S/C37H48O15/c1-8-17(3)26(40)50-19-15-20(49-22(38)9-2)34(28(41)45-6)16-48-23-24(34)33(19)10-11-36(44,29(42)46-7)27(33)31(4,25(23)39)37-21-14-18(32(37,5)52-37)35(43)12-13-47-30(35)51-21/h8,12-13,18-21,23-25,27,30,39,43-44H,9-11,14-16H2,1-7H3/b17-8+/t18?,19-,20+,21+,23+,24+,25+,27?,30-,31+,32?,33-,34-,35?,36+,37?/m0/s1
SMILES	CCC(=O)O[C@@H]1C[C@H](OC(=O)/C(=C/C)/C)[C@]23[C@@H]4[C@@]1(CO[C@H]4[C@H]([C@@](C3[C@@](CC2)(O)C(=O)OC)(C)C12OC2(C)C2C[C@H]1O[C@H]1C2(O)C=CO1)O)C(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	732.3	Volume:	696.091 ? Van der Waals volume.
Dense:	1.052	LogP:	1.673 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.128 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.876 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	38.0
TPSA:	206.11 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	3.0	Rings:	8.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.145	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.607	Fsp³:	0.784
MCE-18:	214.545 ? 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:	0.415	Fluc inhibitor:	0.012 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.017 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.074	Promiscuous compounds:	0.393

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.164	MDCK Permeability:	-4.903
Pgp-inhibitor:	0.0	Pgp-substrate:	0.916
PAMPA:	0.997 ? 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%):	0.194	30% Bioavailability (F30%):	0.388
50% Bioavailability (F50%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	1.0
Plasma Protein Binding (PPB):	49.272%	Volume Distribution (VD):	-0.325
Fu:	51.006% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.484
OATP1B3 inhibitor:	0.339	BCRP inhibitor:	0.006
BSEP inhibitor:	0.972

ADMET: Metabolism

CYP1A2-inhibitor:	0.05	CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.033	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.779	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.993 ? 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):

6.803

Half-life (T1/2):

2.228

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.154
Human Hepatotoxicity (H-HT):	0.771	Drug-induced Liver Injury (DILI):	0.964
AMES Toxicity:	0.952	Rat Oral Acute Toxicity:	0.816
Maximum Recommended Daily Dose:	0.931	Skin Sensitization:	1.0
Carcinogencity:	0.674	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.721
Drug-induced Neurotoxicity:	0.597	Ototoxicity:	0.95
Hematotoxicity:	0.579	Drug-induced Nephrotoxicity:	0.981
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.379
A549 Cytotoxicity:	0.351	Hek293 Cytotoxicity:	0.327
BCF:	0.438 ? 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:	3.695 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.016 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.923 ? 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
NPO10033	Turraea pubescens	Species	Meliaceae	Eukaryota	twig	Dongfang, Hainan Province, China	2010-Mar	PMID[23734701]
NPO10033	Turraea pubescens	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10033	Turraea pubescens	Species	Meliaceae	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	2
mortality	3

Activity Type	# Activity
Cell line	2
Organism	3

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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	>	20000.0	nM	PMID[18278869]
NPT116	Cell line	HL-60	Homo sapiens	IC50	<	10000.0	nM	PMID[18980381]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	mortality	=	0.0	%	PMID[23734701]
NPT176	Organism	Artemia salina	Artemia salina	mortality	=	5.3	%	PMID[23734701]
NPT176	Organism	Artemia salina	Artemia salina	mortality	=	100.0	%	PMID[23734701]

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 NPC471172 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	21794
0.1-0.2	27153
0.2-0.3	884
0.3-0.4	8
0.4-0.5	4
0.5-0.6	4
0.6-0.7	10
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	Natural Product ID
0.71	Intermediate Similarity	NPC48414
0.6931	Remote Similarity	NPC48813
0.6863	Remote Similarity	NPC5153
0.6733	Remote Similarity	NPC194854
0.6731	Remote Similarity	NPC16729
0.6731	Remote Similarity	NPC475462
0.6731	Remote Similarity	NPC120958
0.6476	Remote Similarity	NPC471171
0.625	Remote Similarity	NPC219058
0.6238	Remote Similarity	NPC256618
0.619	Remote Similarity	NPC42206
0.534	Remote Similarity	NPC475376
0.5315	Remote Similarity	NPC601017
0.5315	Remote Similarity	NPC601069
0.5315	Remote Similarity	NPC608590

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471172 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7586
0.1-0.2	1557
0.2-0.3	7
0.3-0.4	0
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