NPASS Compound

Natural Product: NPC476887

Natural Product ID	NPC476887
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2R,4aS,6aS,6aS,6bR,8aS,9R,10S,12S,12aS,14bS)-10,12-dihydroxy-2,4a,6a,6b,12a-pentamethyl-9-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]-3,4,5,6,6a,7,8,8a,9,10,11,12,13,14b-tetradecahydro-1H-picene-2-carboxylic acid
IUPAC Name	(2R,4aS,6aS,6aS,6bR,8aS,9R,10S,12S,12aS,14bS)-10,12-dihydroxy-2,4a,6a,6b,12a-pentamethyl-9-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]-3,4,5,6,6a,7,8,8a,9,10,11,12,13,14b-tetradecahydro-1H-picene-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	45268132
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 100105 0 0 0 0 0 0 0 0999 V2000 6.1858 0.8436 -2.8647 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2327 -0.0859 -2.2317 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0098 0.6176 -1.2043 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8609 0.1653 0.2096 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0849 -1.1296 0.3423 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9361 -1.0608 -0.6003 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5736 -1.2352 -1.8802 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0393 -2.0676 -0.4674 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7147 -1.7878 -0.5044 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1496 -0.8640 0.5572 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6887 -0.7162 0.2481 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4491 0.1986 -0.9309 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0687 -0.1848 -1.4385 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9088 0.3077 -0.3819 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5805 -0.0696 1.0081 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8552 -0.2245 1.3949 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9123 -1.3490 2.4296 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2419 -1.9102 2.6921 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3934 -1.4528 1.8852 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0643 -0.4850 2.6751 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0675 -2.3808 1.9505 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4568 0.9893 2.0603 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3715 0.8656 1.9071 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8347 0.6315 1.5566 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2293 0.1451 0.4012 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2832 -0.2366 -0.7185 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7614 0.2734 -2.0386 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2157 0.0977 -2.2764 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0391 0.6881 -1.1183 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6597 -0.1174 0.0875 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6362 -0.1581 1.1704 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8296 0.7562 1.0647 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3454 0.9457 -0.3272 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4961 0.3822 -1.4011 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5215 2.0711 1.7410 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9632 0.1408 1.8439 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4982 0.7258 2.8106 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4578 -1.1150 1.5082 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7574 2.1382 -1.0726 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2869 -1.7533 -0.7194 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9679 1.8102 -0.6028 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7251 -1.4001 1.6441 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1977 1.1114 0.9920 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3828 0.5894 -1.5334 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3130 0.2885 -3.2242 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6182 1.3874 -3.7389 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9273 1.6291 -2.1113 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8998 -0.3635 -3.1012 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7453 1.7137 -1.2277 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8460 -0.0044 0.6911 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7770 -1.9739 0.0075 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4976 -0.0362 -0.6031 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1872 -2.7977 -0.4301 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3709 -1.4480 -1.5346 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6316 0.1301 0.3888 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3037 -1.7208 -0.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3587 1.2666 -0.5732 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2234 0.2029 -1.6883 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0496 -1.2524 -1.6223 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0923 0.4256 -2.3581 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0828 -1.0745 1.1820 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4847 -0.9285 3.3737 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1884 -3.0337 2.5421 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4710 -1.8558 3.8097 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1598 -2.2841 1.7934 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1089 -0.7822 3.6240 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6222 -2.5777 2.6272 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7130 0.7640 3.1132 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7116 1.8072 2.1217 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3922 1.3219 1.5646 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2605 0.5747 2.9567 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1888 1.9272 1.7415 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5699 0.8856 2.2937 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4251 1.3093 -2.2791 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2362 -0.3564 -2.8191 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5242 0.6280 -3.1801 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4764 -0.9743 -2.3887 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6322 -1.1846 -0.3423 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2251 -0.0321 2.1843 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1076 -1.2023 1.2482 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3891 0.5489 -0.4800 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4645 2.0569 -0.4874 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8134 0.8167 -2.3738 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6049 -0.7164 -1.4464 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0186 2.8716 1.1512 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4596 2.2621 1.9189 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0049 2.1422 2.7596 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9892 -1.6470 2.2001 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0794 2.4822 -1.9099 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3218 2.5367 -0.1608 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7032 2.7281 -1.2590 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9577 -2.1915 0.0627 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6452 -2.1479 -1.6911 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2945 -2.1995 -0.5054 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6951 2.0961 -1.6570 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9608 2.2487 -0.4138 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2452 2.3753 0.0159 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7592 -2.3772 1.7975 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1846 0.7465 1.9252 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5207 0.2790 -2.4640 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 6 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 17 21 1 0 16 22 1 1 15 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 1 32 36 1 0 36 37 2 0 36 38 1 0 29 39 1 1 26 40 1 6 14 41 1 1 5 42 1 0 4 43 1 0 3 44 1 0 7 2 1 0 19 10 1 0 16 11 1 0 26 14 1 0 30 25 1 0 34 29 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 6 3 49 1 1 4 50 1 1 5 51 1 6 6 52 1 6 9 53 1 0 9 54 1 0 10 55 1 1 11 56 1 6 12 57 1 0 12 58 1 0 13 59 1 0 13 60 1 0 15 61 1 1 17 62 1 1 18 63 1 0 18 64 1 0 19 65 1 6 20 66 1 0 21 67 1 0 22 68 1 0 22 69 1 0 22 70 1 0 23 71 1 0 23 72 1 0 24 73 1 0 27 74 1 0 27 75 1 0 28 76 1 0 28 77 1 0 30 78 1 6 31 79 1 0 31 80 1 0 33 81 1 0 33 82 1 0 34 83 1 0 34 84 1 0 35 85 1 0 35 86 1 0 35 87 1 0 38 88 1 0 39 89 1 0 39 90 1 0 39 91 1 0 40 92 1 0 40 93 1 0 40 94 1 0 41 95 1 0 41 96 1 0 41 97 1 0 42 98 1 0 43 99 1 0 44100 1 0 M END

Standard InCHIKey	DCZZMOKZJIBKQP-DBQYPUSDSA-N
Standard InCHI	InChI=1S/C35H56O9/c1-18-26(38)27(39)28(40)29(44-18)43-17-19-20-9-10-34(5)24(35(20,6)25(37)15-23(19)36)8-7-21-22-16-32(3,30(41)42)12-11-31(22,2)13-14-33(21,34)4/h7,18-20,22-29,36-40H,8-17H2,1-6H3,(H,41,42)/t18-,19-,20-,22+,23-,24-,25-,26-,27+,28+,29+,31+,32+,33+,34+,35-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@H]2[C@@H]3CC[C@@]4([C@@H]([C@]3([C@H](C[C@@H]2O)O)C)CC=C5[C@]4(CC[C@@]6([C@@H]5C[C@](CC6)(C)C(=O)O)C)C)C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	620.39	Volume:	636.416 ? Van der Waals volume.
Dense:	0.975	LogP:	2.9 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.106 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.669 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	33.0
TPSA:	156.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	9.0

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:	5.576	Fsp³:	0.914
MCE-18:	126.328 ? 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:	0.798	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.032 ? 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:	0.184	Promiscuous compounds:	0.142

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.615	MDCK Permeability:	-5.136
Pgp-inhibitor:	0.0	Pgp-substrate:	0.078
PAMPA:	1.0 ? 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%):	0.586	30% Bioavailability (F30%):	0.297
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.568	MRP1:	0.727
Plasma Protein Binding (PPB):	83.34%	Volume Distribution (VD):	-0.491
Fu:	12.338% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.935	BCRP inhibitor:	0.208
BSEP inhibitor:	0.022

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:	0.0
CYP3A4-inhibitor:	0.839	CYP3A4-substrate:	0.92
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.572
HLM stability:	0.0 ? 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):

1.134

Half-life (T1/2):

3.352

ADMET: Toxicity

hERG Blockers:	0.044	hERG Blockers (10um):	0.088
Human Hepatotoxicity (H-HT):	0.636	Drug-induced Liver Injury (DILI):	0.612
AMES Toxicity:	0.199	Rat Oral Acute Toxicity:	0.141
Maximum Recommended Daily Dose:	0.266	Skin Sensitization:	0.957
Carcinogencity:	0.621	Eye Corrosion:	0.0
Eye Irritation:	0.017	Respiratory Toxicity:	0.485
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.926
Hematotoxicity:	0.221	Drug-induced Nephrotoxicity:	0.887
Genotoxicity:	0.306	RPMI-8226 Immunitoxicity:	0.091
A549 Cytotoxicity:	0.148	Hek293 Cytotoxicity:	0.259
BCF:	0.873 ? 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:	3.617 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.259 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.392 ? 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
NPO33642	Combretum sundaicum	Species	Combretaceae	Eukaryota	leaves, flowers	Bac Son, Lang Son Province, Vietnam	1997-JUL	PMID[19572612]
NPO33642	Combretum sundaicum	Species	Combretaceae	Eukaryota	leaves	Bac Son, Lang Son Province, Vietnam	1997-JUL	PMID[19572612]
NPO33642	Combretum sundaicum	Species	Combretaceae	Eukaryota	flowers	Bac Son, Lang Son Province, Vietnam	1997-JUL	PMID[19572612]

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
IC50	3

Activity Type	# Activity
Individual protein	1
Cell line	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2796	Individual protein	Apoptosis regulator Bcl-X	Homo sapiens	Ki	>	100000	nM	PMID[19572612]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell line	KB	Homo sapiens	IC50	=	11600	nM	PMID[19572612]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	24700	nM	PMID[19572612]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	32700	nM	PMID[19572612]

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 NPC476887 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	20916
0.1-0.2	24081
0.2-0.3	3826
0.3-0.4	918
0.4-0.5	100
0.5-0.6	12
0.6-0.7	4
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
0.6989	Remote Similarity	NPC476886
0.6562	Remote Similarity	NPC476881
0.6526	Remote Similarity	NPC476882
0.6	Remote Similarity	NPC476880
0.5761	Remote Similarity	NPC476878
0.5714	Remote Similarity	NPC171203
0.5714	Remote Similarity	NPC307426
0.5714	Remote Similarity	NPC98442
0.5714	Remote Similarity	NPC242468
0.5534	Remote Similarity	NPC482751
0.549	Remote Similarity	NPC309780
0.5455	Remote Similarity	NPC474529
0.5341	Remote Similarity	NPC263393
0.5288	Remote Similarity	NPC482748
0.5227	Remote Similarity	NPC155120
0.5227	Remote Similarity	NPC288833

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476887 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6465
0.1-0.2	2609
0.2-0.3	68
0.3-0.4	6
0.4-0.5	2
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