NPASS Compound

Natural Product: NPC508432

Natural Product ID	NPC508432
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] (2~{R},4~{a}~{R},6~{a}~{R},6~{a}~{S},6~{b}~{R},8~{a}~{R},9~{R},10~{S},12~{a}~{R},14~{b}~{S})-10-hydroxy-2,9-bis(hydroxymethyl)-2,6~{a},6~{b},9,12~{a}-pentamethyl-1,3,4,5,6,6~{a},7,8,8~{a},10,11,12,13,14~{b}-tetradecahydropicene-4~{a}-carboxylate
IUPAC Name	[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] (2~{R},4~{a}~{R},6~{a}~{R},6~{a}~{S},6~{b}~{R},8~{a}~{R},9~{R},10~{S},12~{a}~{R},14~{b}~{S})-10-hydroxy-2,9-bis(hydroxymethyl)-2,6~{a},6~{b},9,12~{a}-pentamethyl-1,3,4,5,6,6~{a},7,8,8~{a},10,11,12,13,14~{b}-tetradecahydropicene-4~{a}-carboxylate
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 104109 0 0 0 0 0 0 0 0999 V2000 3.6812 3.2902 -0.7754 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8495 2.4185 -1.7162 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7792 3.2327 -3.0208 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1686 4.4470 -2.7381 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5330 1.1332 -2.0656 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5028 0.0036 -2.2136 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9376 -0.1673 -0.8029 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1394 -0.2337 0.0998 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2407 0.6302 1.0126 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1260 -1.1667 -0.0047 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2171 -1.1787 0.8607 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4466 -1.0126 0.2353 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3233 -0.5199 1.2234 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6650 -0.2171 0.5601 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0980 -1.4531 0.0293 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5681 -1.6566 2.1887 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4399 -1.2971 3.2065 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3136 -2.2158 2.7825 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6122 -3.4425 3.3740 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2432 -2.4344 1.7340 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0043 -2.4516 2.4084 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2528 -1.4913 -0.6568 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0372 -1.3915 0.2414 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9838 -0.5625 -0.5632 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1189 -1.2240 -1.8775 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3718 0.7959 -0.5868 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1285 1.8767 -0.6819 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5910 1.8208 -0.7701 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1566 0.4943 -0.4345 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5865 0.5997 0.1233 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6826 1.2812 1.4088 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3434 1.4131 -0.9081 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8183 1.4455 -0.5835 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3734 0.0762 -0.5858 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6349 0.1511 0.0616 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5901 -0.9883 0.1254 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1173 -1.1069 1.5302 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9569 -2.2626 -0.6564 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4062 -3.4102 -0.2417 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1295 -0.8040 0.0246 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3037 -1.7279 0.9103 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9432 -1.8535 0.2118 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2858 -0.4714 0.2426 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8744 -0.2431 1.6435 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1010 1.0224 -0.4993 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4431 2.2700 -1.2220 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6792 4.3515 -1.0755 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7056 2.8710 -0.6859 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2479 3.2750 0.2629 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7892 3.3990 -3.4240 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1100 2.6856 -3.7225 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6771 5.2213 -3.0382 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2090 0.8680 -1.2479 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1129 1.1803 -2.9983 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0696 -0.9056 -2.4464 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7473 0.2775 -2.9475 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1110 -0.3402 1.5793 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9180 0.3790 1.7108 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4876 0.4627 -0.3008 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3672 0.1840 1.2900 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9588 -1.2500 -0.4288 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0792 -2.4677 1.6058 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4592 -0.3342 3.3988 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9557 -1.5410 3.5989 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1490 -3.3320 4.1830 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4309 -3.3445 1.1667 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9938 -1.8341 3.1614 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9066 -2.2707 -0.1642 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0445 -1.9111 -1.6550 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4074 -0.7773 1.1170 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3522 -2.3606 0.5438 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3641 -0.7863 -2.5950 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0686 -1.1552 -2.3995 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9347 -2.3363 -1.7751 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6715 2.8936 -0.6958 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0380 2.6565 -0.1501 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8450 2.1596 -1.8215 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3925 0.0173 -1.4439 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7209 1.8507 1.5908 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4367 2.1275 1.4496 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8810 0.6960 2.2982 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9327 2.4143 -1.0495 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2506 0.8473 -1.8693 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0937 1.9790 0.3183 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2931 2.0006 -1.4303 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6653 -0.2469 -1.6373 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3243 0.5153 -0.5626 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4117 -0.0949 1.8880 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4477 -1.6434 2.2109 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0603 -1.6958 1.4776 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0805 -2.3845 -0.6555 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7218 -2.0749 -1.7455 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8443 -3.9102 0.4716 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8530 -1.1265 -1.0142 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7317 -2.7014 0.9797 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1918 -1.3208 1.9309 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1630 -2.1884 -0.8087 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3648 -2.5875 0.7733 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3706 -1.2077 1.9726 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0907 0.5303 1.7755 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6357 -0.0985 2.3978 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2694 1.2356 0.6065 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7349 2.4238 -2.0627 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2855 3.1637 -0.5419 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 2 3 1 0 3 4 1 0 2 5 1 0 5 6 1 0 6 7 1 0 7 8 1 1 8 9 2 0 8 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 7 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 1 30 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 34 36 1 0 36 37 1 1 36 38 1 0 38 39 1 0 36 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 1 26 45 1 0 45 46 1 0 46 2 1 0 45 7 1 0 20 11 1 0 43 24 1 0 43 29 1 0 40 30 1 0 1 47 1 0 1 48 1 0 1 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 5 53 1 0 5 54 1 0 6 55 1 0 6 56 1 0 11 57 1 1 13 58 1 1 14 59 1 0 14 60 1 0 15 61 1 0 16 62 1 6 17 63 1 0 18 64 1 1 19 65 1 0 20 66 1 6 21 67 1 0 22 68 1 0 22 69 1 0 23 70 1 0 23 71 1 0 25 72 1 0 25 73 1 0 25 74 1 0 27 75 1 0 28 76 1 0 28 77 1 0 29 78 1 6 31 79 1 0 31 80 1 0 31 81 1 0 32 82 1 0 32 83 1 0 33 84 1 0 33 85 1 0 34 86 1 6 35 87 1 0 37 88 1 0 37 89 1 0 37 90 1 0 38 91 1 0 38 92 1 0 39 93 1 0 40 94 1 6 41 95 1 0 41 96 1 0 42 97 1 0 42 98 1 0 44 99 1 0 44100 1 0 44101 1 0 45102 1 1 46103 1 0 46104 1 0 M END

Standard InCHIKey	AVGSQQXPYYPWLU-PENQKJCWSA-N
Standard InCHI	InChI=1S/C36H58O10/c1-31(18-38)12-14-36(30(44)46-29-28(43)27(42)26(41)22(17-37)45-29)15-13-34(4)20(21(36)16-31)6-7-24-32(2)10-9-25(40)33(3,19-39)23(32)8-11-35(24,34)5/h6,21-29,37-43H,7-19H2,1-5H3/t21-,22+,23+,24+,25-,26+,27-,28+,29-,31+,32-,33-,34+,35+,36-/m0/s1
SMILES	C[C@@]1(CO)CC[C@]2(C(=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)[C@@](C)(CO)[C@@H]5CC[C@]43C)[C@@H]2C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	650.4	Volume:	662.503 ? Van der Waals volume.
Dense:	0.982	LogP:	1.955 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.246 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.799 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	33.0
TPSA:	177.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	7.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.173	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.486	Fsp³:	0.917
MCE-18:	128.058 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.907	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? 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:	0.057

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.147	MDCK Permeability:	-5.161
Pgp-inhibitor:	0.0	Pgp-substrate:	0.03
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):	0.272
20% Bioavailability (F20%):	0.996	30% Bioavailability (F30%):	0.963
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.69	MRP1:	0.115
Plasma Protein Binding (PPB):	70.534%	Volume Distribution (VD):	-0.364
Fu:	22.324% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.143	BCRP inhibitor:	0.394
BSEP inhibitor:	0.23

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.623
HLM stability:	0.003 ? 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):

1.275

Half-life (T1/2):

2.227

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.017
Human Hepatotoxicity (H-HT):	0.826	Drug-induced Liver Injury (DILI):	0.144
AMES Toxicity:	0.698	Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.039	Skin Sensitization:	1.0
Carcinogencity:	0.772	Eye Corrosion:	0.0
Eye Irritation:	0.008	Respiratory Toxicity:	0.037
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.986
Hematotoxicity:	0.555	Drug-induced Nephrotoxicity:	0.981
Genotoxicity:	0.09	RPMI-8226 Immunitoxicity:	0.062
A549 Cytotoxicity:	0.847	Hek293 Cytotoxicity:	0.21
BCF:	0.81 ? 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:	3.483 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.094 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.254 ? 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
NPO55292	Kalidium foliatum	Species	Chenopodiaceae	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

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 NPC508432 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	20469
0.1-0.2	23485
0.2-0.3	4516
0.3-0.4	995
0.4-0.5	246
0.5-0.6	98
0.6-0.7	31
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8919	High Similarity	NPC237503
0.8205	Intermediate Similarity	NPC68419
0.7952	Intermediate Similarity	NPC29069
0.7922	Intermediate Similarity	NPC167383
0.7625	Intermediate Similarity	NPC37739
0.7531	Intermediate Similarity	NPC137917
0.7412	Intermediate Similarity	NPC90856
0.7195	Intermediate Similarity	NPC306746
0.7	Intermediate Similarity	NPC191763
0.6747	Remote Similarity	NPC46388
0.6632	Remote Similarity	NPC102439
0.6628	Remote Similarity	NPC110139
0.6628	Remote Similarity	NPC108709
0.6471	Remote Similarity	NPC116794
0.6471	Remote Similarity	NPC190837
0.6452	Remote Similarity	NPC473373
0.6444	Remote Similarity	NPC214484
0.6395	Remote Similarity	NPC199457
0.6344	Remote Similarity	NPC235405
0.6304	Remote Similarity	NPC48499
0.6289	Remote Similarity	NPC473459
0.6277	Remote Similarity	NPC249848
0.6277	Remote Similarity	NPC107966
0.625	Remote Similarity	NPC271138
0.625	Remote Similarity	NPC102914
0.6238	Remote Similarity	NPC480474
0.6222	Remote Similarity	NPC209894
0.6211	Remote Similarity	NPC295371
0.6211	Remote Similarity	NPC473884
0.618	Remote Similarity	NPC220984
0.617	Remote Similarity	NPC139894
0.617	Remote Similarity	NPC475516
0.6146	Remote Similarity	NPC473343
0.6105	Remote Similarity	NPC150400
0.6042	Remote Similarity	NPC39211
0.6042	Remote Similarity	NPC157868
0.602	Remote Similarity	NPC109588
0.602	Remote Similarity	NPC104071
0.602	Remote Similarity	NPC30735
0.602	Remote Similarity	NPC309714
0.5979	Remote Similarity	NPC469946
0.5977	Remote Similarity	NPC605954
0.596	Remote Similarity	NPC40775
0.596	Remote Similarity	NPC101744
0.5955	Remote Similarity	NPC604133
0.5934	Remote Similarity	NPC256798
0.5918	Remote Similarity	NPC192791
0.5918	Remote Similarity	NPC223301
0.5918	Remote Similarity	NPC242840
0.5918	Remote Similarity	NPC171544
0.5918	Remote Similarity	NPC112352
0.59	Remote Similarity	NPC235438
0.5816	Remote Similarity	NPC475171
0.58	Remote Similarity	NPC10607
0.58	Remote Similarity	NPC251768
0.58	Remote Similarity	NPC159309
0.58	Remote Similarity	NPC11551
0.58	Remote Similarity	NPC46665
0.58	Remote Similarity	NPC480475
0.58	Remote Similarity	NPC86222
0.5789	Remote Similarity	NPC179434
0.5778	Remote Similarity	NPC7870
0.5778	Remote Similarity	NPC310014
0.5778	Remote Similarity	NPC269315
0.5778	Remote Similarity	NPC75747
0.5761	Remote Similarity	NPC128925
0.5745	Remote Similarity	NPC189884
0.5745	Remote Similarity	NPC138334
0.5743	Remote Similarity	NPC475591
0.5743	Remote Similarity	NPC63159
0.5743	Remote Similarity	NPC236870
0.5728	Remote Similarity	NPC281148
0.5686	Remote Similarity	NPC222580
0.5686	Remote Similarity	NPC297263
0.5638	Remote Similarity	NPC47063
0.5579	Remote Similarity	NPC204458
0.5579	Remote Similarity	NPC269095
0.5577	Remote Similarity	NPC104372
0.5577	Remote Similarity	NPC114484
0.557	Remote Similarity	NPC246708
0.5534	Remote Similarity	NPC31193
0.5524	Remote Similarity	NPC301449
0.5524	Remote Similarity	NPC601290
0.5521	Remote Similarity	NPC78046
0.5472	Remote Similarity	NPC481030
0.5472	Remote Similarity	NPC480473
0.5472	Remote Similarity	NPC80986
0.5421	Remote Similarity	NPC31838
0.5421	Remote Similarity	NPC481078
0.5421	Remote Similarity	NPC187290
0.5385	Remote Similarity	NPC609763
0.5357	Remote Similarity	NPC100639
0.5327	Remote Similarity	NPC241909
0.5306	Remote Similarity	NPC475208
0.53	Remote Similarity	NPC58448
0.5294	Remote Similarity	NPC75417
0.5269	Remote Similarity	NPC187056
0.5269	Remote Similarity	NPC212968
0.5269	Remote Similarity	NPC606216
0.5269	Remote Similarity	NPC607023
0.5268	Remote Similarity	NPC135904
0.5256	Remote Similarity	NPC196753
0.5244	Remote Similarity	NPC213412
0.5238	Remote Similarity	NPC475504
0.5234	Remote Similarity	NPC481079
0.5225	Remote Similarity	NPC79643
0.5221	Remote Similarity	NPC475160
0.5221	Remote Similarity	NPC470218
0.5221	Remote Similarity	NPC471550
0.5221	Remote Similarity	NPC473714
0.5204	Remote Similarity	NPC1046
0.5196	Remote Similarity	NPC471547
0.5196	Remote Similarity	NPC161674
0.5192	Remote Similarity	NPC305267
0.5185	Remote Similarity	NPC295823
0.5185	Remote Similarity	NPC174720
0.5185	Remote Similarity	NPC475467
0.5179	Remote Similarity	NPC481031
0.5143	Remote Similarity	NPC148417
0.5135	Remote Similarity	NPC76972
0.5135	Remote Similarity	NPC469782
0.5135	Remote Similarity	NPC204414
0.5133	Remote Similarity	NPC123199
0.513	Remote Similarity	NPC481080
0.5125	Remote Similarity	NPC230295
0.5125	Remote Similarity	NPC98386
0.5109	Remote Similarity	NPC285576
0.5106	Remote Similarity	NPC48249
0.5096	Remote Similarity	NPC471548
0.5096	Remote Similarity	NPC160415
0.5091	Remote Similarity	NPC75287
0.5089	Remote Similarity	NPC192600
0.5086	Remote Similarity	NPC476068
0.5085	Remote Similarity	NPC65105
0.5048	Remote Similarity	NPC473401
0.5047	Remote Similarity	NPC134835
0.5046	Remote Similarity	NPC96641
0.5046	Remote Similarity	NPC163183

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC508432 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7305
0.1-0.2	1769
0.2-0.3	70
0.3-0.4	5
0.4-0.5	0
0.5-0.6	1
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
0.5366	Remote Similarity	NPD7645	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