NPASS Compound

Natural Product: NPC488523

Natural Product ID	NPC488523
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OWYZSZOAYIZNEY-AOWDRKLESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10627759
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 107111 0 0 0 0 0 0 0 0999 V2000 8.4130 0.8432 1.3532 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9836 0.2689 0.0990 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0345 -1.2394 0.1223 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6696 -1.7915 0.2793 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4437 -3.0216 0.3419 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6049 -0.9116 0.3586 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2558 -1.3296 0.5062 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6600 -0.8357 1.7491 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2136 -0.5143 1.7894 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6924 0.1515 0.4961 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3270 1.4880 0.5026 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1370 -0.7848 -0.6050 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3457 -0.6489 -1.8701 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3246 0.4293 -1.8934 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4779 0.5982 -0.6901 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1197 2.0758 -0.6377 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2081 0.0913 0.4917 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5259 0.5211 1.7800 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7985 -0.1364 1.7438 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4030 -0.4100 0.6404 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7098 -1.0630 0.6700 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1242 -1.7326 1.9108 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3929 -2.4862 1.5774 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0045 -3.8011 0.8801 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0738 -2.8937 2.8712 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3721 -1.8126 0.7161 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8005 -1.0299 -0.4468 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7448 -0.1110 0.2193 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2221 0.9224 -0.7169 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9387 0.6428 -1.4372 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8775 -0.1145 -0.7089 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7436 -1.4247 -1.5221 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2310 1.1968 -1.6669 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8458 2.4173 -1.8713 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4802 3.3864 -1.1597 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8999 2.6298 -2.8767 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3365 4.0723 -2.8421 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8680 4.3722 -1.4650 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5459 0.5863 1.2293 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3807 0.5697 2.4487 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6169 1.3568 0.8001 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4482 2.0622 1.6823 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5935 -0.9473 -0.7862 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7522 -2.1394 -1.7537 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3059 0.1950 -1.4777 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9816 1.7552 1.6489 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3858 0.0757 2.1665 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3614 1.1683 1.1365 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0104 0.6587 -0.0283 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3857 0.5899 -0.7785 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3860 -1.5347 -0.9114 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7519 -1.5979 0.8912 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3185 -2.4458 0.5512 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8110 -1.6007 2.5772 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2864 0.0245 2.1376 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5501 -1.3592 2.0588 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1076 0.2960 2.5732 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3547 1.4153 0.9851 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7886 2.1111 1.2617 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5330 1.9744 -0.4390 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8189 -1.8100 -0.2131 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8835 -1.5946 -2.2269 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1048 -0.4208 -2.6815 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8038 0.3700 -2.8704 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9326 1.3864 -2.0585 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7551 2.3299 -0.0676 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1837 2.4883 -1.6718 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9665 2.6541 -0.1461 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9914 -1.0269 0.4770 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4290 1.6451 1.8162 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1133 0.2577 2.6638 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2691 -0.3928 2.6707 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6133 -1.9529 -0.0560 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1293 -1.1869 2.8425 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3530 -2.5710 2.1077 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0586 -4.2077 1.2919 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8012 -3.6030 -0.2072 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8334 -4.5266 0.9029 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0515 -2.1052 3.6401 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0750 -3.2763 2.6421 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4978 -3.7809 3.2589 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0702 -1.2117 1.3264 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0088 -2.6128 0.2369 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3279 -1.7179 -1.1484 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5604 -0.3713 -0.8638 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0639 1.8530 -0.1396 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6107 1.6424 -1.8395 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2645 0.1370 -2.4007 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7860 -1.7856 -1.7981 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3999 -1.1016 -2.5335 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1666 -2.1873 -1.0314 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7601 1.9399 -2.7335 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4644 2.4461 -3.8904 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0774 4.3004 -3.6378 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4181 4.6946 -2.9697 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8438 4.9170 -1.5349 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1820 5.0015 -0.8628 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1033 3.4206 -0.9323 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5048 1.9414 1.3326 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1851 3.1372 1.6905 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3395 1.6573 2.7146 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9733 -3.0527 -1.1506 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6218 -2.0023 -2.4169 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8175 -2.3519 -2.3065 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1387 -0.2052 -2.1354 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8802 0.8409 -0.7528 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6737 0.7673 -2.1594 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 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 6 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 23 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 6 29 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 1 0 37 38 1 0 28 39 1 1 39 40 2 0 39 41 1 0 41 42 1 0 12 43 1 0 43 44 1 0 43 45 1 0 43 7 1 0 17 10 1 0 31 20 1 0 31 15 1 0 28 21 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 0 2 50 1 0 3 51 1 0 3 52 1 0 7 53 1 1 8 54 1 0 8 55 1 0 9 56 1 0 9 57 1 0 11 58 1 0 11 59 1 0 11 60 1 0 12 61 1 1 13 62 1 0 13 63 1 0 14 64 1 0 14 65 1 0 16 66 1 0 16 67 1 0 16 68 1 0 17 69 1 6 18 70 1 0 18 71 1 0 19 72 1 0 21 73 1 6 22 74 1 0 22 75 1 0 24 76 1 0 24 77 1 0 24 78 1 0 25 79 1 0 25 80 1 0 25 81 1 0 26 82 1 0 26 83 1 0 27 84 1 0 27 85 1 0 29 86 1 1 30 87 1 0 30 88 1 0 32 89 1 0 32 90 1 0 32 91 1 0 36 92 1 0 36 93 1 0 37 94 1 0 37 95 1 0 38 96 1 0 38 97 1 0 38 98 1 0 42 99 1 0 42100 1 0 42101 1 0 44102 1 0 44103 1 0 44104 1 0 45105 1 0 45106 1 0 45107 1 0 M END

Standard InCHIKey	OWYZSZOAYIZNEY-AOWDRKLESA-N
Standard InCHI	InChI=1S/C39H62O6/c1-11-13-31(40)44-29-18-19-36(7)27(35(29,5)6)17-20-37(8)28(36)16-15-25-26-23-34(3,4)21-22-39(26,33(42)43-10)30(24-38(25,37)9)45-32(41)14-12-2/h15,26-30H,11-14,16-24H2,1-10H3/t26-,27+,28-,29+,30-,36+,37-,38-,39-/m1/s1
SMILES	CCCC(=O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@H]4CC(C)(C)CC[C@@]4([C@@H](C[C@@]32C)OC(=O)CCC)C(=O)OC)C1(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	626.45	Volume:	682.513 ? Van der Waals volume.
Dense:	0.918	LogP:	6.818 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.881 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-8.269 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	29.0
TPSA:	78.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.159	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.011	Fsp³:	0.872
MCE-18:	107.014 ? 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:	0.949	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.466	Promiscuous compounds:	0.326

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.777	MDCK Permeability:	-4.801
Pgp-inhibitor:	0.997	Pgp-substrate:	0.031
PAMPA:	0.036 ? 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%):	0.914	30% Bioavailability (F30%):	0.864
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.255	MRP1:	0.796
Plasma Protein Binding (PPB):	94.736%	Volume Distribution (VD):	0.17
Fu:	5.756% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.358
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.996
CYP2C19-inhibitor:	0.986	CYP2C19-substrate:	0.278
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.195
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.972
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

8.233

Half-life (T1/2):

0.506

ADMET: Toxicity

hERG Blockers:	0.266	hERG Blockers (10um):	0.459
Human Hepatotoxicity (H-HT):	0.651	Drug-induced Liver Injury (DILI):	0.494
AMES Toxicity:	0.076	Rat Oral Acute Toxicity:	0.289
Maximum Recommended Daily Dose:	0.708	Skin Sensitization:	0.845
Carcinogencity:	0.785	Eye Corrosion:	0.007
Eye Irritation:	0.086	Respiratory Toxicity:	0.636
Drug-induced Neurotoxicity:	0.107	Ototoxicity:	0.568
Hematotoxicity:	0.408	Drug-induced Nephrotoxicity:	0.739
Genotoxicity:	0.226	RPMI-8226 Immunitoxicity:	0.06
A549 Cytotoxicity:	0.157	Hek293 Cytotoxicity:	0.385
BCF:	2.61 ? 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:	5.336 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.525 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.497 ? 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
NPO27443	Gymnocladus chinensis	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[7494144]
NPO7631	Gleditsia japonica	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[7494144]
NPO7631	Gleditsia japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7631	Gleditsia japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27443	Gymnocladus chinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7631	Gleditsia japonica	Species	Fabaceae	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
EC50	1
IC50	1

Activity Type	# Activity
Cell line	1
Organism	1

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
NPT759	Cell line	H9	Homo sapiens	IC50	>	160000.0	nM	PMID[7494144]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	15000.0	nM	PMID[7494144]

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 NPC488523 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	23395
0.1-0.2	22970
0.2-0.3	2778
0.3-0.4	611
0.4-0.5	83
0.5-0.6	7
0.6-0.7	11
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
0.9344	High Similarity	NPC488525
0.7042	Intermediate Similarity	NPC488522
0.697	Remote Similarity	NPC162107
0.697	Remote Similarity	NPC46912
0.6866	Remote Similarity	NPC10005
0.6866	Remote Similarity	NPC91525
0.6622	Remote Similarity	NPC488524
0.6615	Remote Similarity	NPC195334
0.6515	Remote Similarity	NPC224145
0.6301	Remote Similarity	NPC488520
0.6143	Remote Similarity	NPC191965
0.6133	Remote Similarity	NPC86368
0.6056	Remote Similarity	NPC286786
0.5915	Remote Similarity	NPC9892
0.5479	Remote Similarity	NPC329943
0.5342	Remote Similarity	NPC127855
0.5256	Remote Similarity	NPC488521
0.5211	Remote Similarity	NPC290495
0.5068	Remote Similarity	NPC267517
0.5065	Remote Similarity	NPC120840

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488523 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7365
0.1-0.2	1732
0.2-0.3	47
0.3-0.4	5
0.4-0.5	1
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