NPASS Compound

Natural Product: NPC50068

Natural Product ID	NPC50068
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OHKPPWRIPKRDGS-YSUNMYHASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

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 111117 0 0 0 0 0 0 0 0999 V2000 10.5773 0.0611 -2.5826 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3508 0.5079 -1.8617 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1502 1.7264 -1.7835 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4071 -0.4425 -1.2618 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5197 -1.7605 -1.2838 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3479 -2.3831 -0.5599 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3254 -1.3053 -0.7889 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1425 -1.3067 0.0925 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2313 -2.4621 -0.2776 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8102 -2.2017 0.0023 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2854 -1.0675 0.4789 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8091 -0.9862 0.7021 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2712 0.3626 0.9705 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3027 1.3629 1.4701 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4947 1.3502 0.5738 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2303 0.0440 0.7570 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8672 -0.0831 2.1182 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3417 -0.0608 -0.2600 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1360 1.1876 -0.3069 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4417 1.0875 -1.0641 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1932 -0.0900 -0.5333 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5614 0.0794 0.9205 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8233 0.3374 1.8607 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9537 0.8585 1.2378 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1316 -0.0594 1.3232 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3973 0.6831 1.6767 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4411 2.0426 0.9918 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1373 2.7713 1.2009 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3275 4.0931 1.8961 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1806 4.9632 1.2276 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2678 2.0136 1.9930 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7392 1.8668 -0.3330 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9164 2.4580 -0.7623 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7219 3.3815 -1.9248 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9536 4.2282 -2.0603 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1556 3.4498 -1.6497 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9520 1.9733 -1.7901 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8891 1.5003 -1.0720 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4991 3.7179 -0.3032 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0411 4.7331 -3.3564 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5733 4.1486 -1.7061 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5762 0.8167 3.0492 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3232 -0.8069 0.1589 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2011 -2.1707 0.3393 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4438 -2.9528 -0.0182 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2121 -4.3856 0.4843 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8205 -4.8298 0.1685 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2509 -3.9211 -0.8701 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8013 -4.3701 -1.0981 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2020 -2.5933 -0.5401 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9167 -6.1091 -0.4239 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4079 -4.3913 1.8593 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5911 -2.5157 0.5940 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5038 -1.0264 -2.7337 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6298 0.5838 -3.5650 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4886 0.3637 -2.0263 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3082 -2.3409 -1.7367 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0606 -3.3437 -1.0047 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5848 -2.4176 0.5135 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9917 -1.2435 -1.8412 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3436 -1.4127 1.1602 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3651 -2.7073 -1.3560 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5354 -3.3556 0.3295 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1176 -3.0095 -0.1973 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6005 -1.6924 1.5595 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2613 -1.4790 -0.1567 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1102 0.7967 0.0250 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4761 1.1430 2.5206 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8885 2.3943 1.4330 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1742 2.2157 0.7426 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1672 1.4140 -0.4695 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9221 0.3174 2.1337 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3474 0.5010 2.9136 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8370 -1.1451 2.4979 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8856 -0.2369 -1.2442 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2753 1.6902 0.6720 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5245 1.9316 -0.9043 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2646 0.9447 -2.1490 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9740 2.0479 -0.9202 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1038 1.0313 1.2602 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6701 0.2538 1.0180 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2069 -0.7163 1.5722 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7335 1.1363 0.2092 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9282 -0.7820 2.1382 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2523 0.1085 1.2805 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2366 2.6273 1.4767 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6408 2.9467 0.2391 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6603 3.9032 2.9391 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3551 4.6303 1.9884 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9324 5.9060 1.4582 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3297 3.0174 0.0927 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5309 2.8025 -2.8626 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8242 5.0887 -1.3504 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0196 3.7364 -2.3135 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9881 1.6442 -2.8525 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8701 1.4966 -1.3200 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3695 4.6740 -0.1204 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9860 4.5620 -3.6518 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7992 3.5475 -1.9280 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0971 0.0718 3.3911 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9718 -2.3652 1.3872 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6114 -3.0388 -1.1018 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9843 -5.0566 0.0375 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1663 -4.9430 1.0605 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7697 -4.1374 -1.8262 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2932 -4.2437 -0.1090 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8397 -5.4126 -1.4430 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3989 -3.6827 -1.8715 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5675 -6.6701 0.0424 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8308 -5.2477 2.1202 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3594 -2.3728 -0.0092 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 2 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 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 13 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 27 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 35 40 1 0 34 41 1 0 26 42 1 0 25 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 48 50 1 0 47 51 1 0 46 52 1 0 45 53 1 0 21 4 1 0 31 24 1 0 38 33 1 0 50 44 1 0 21 7 1 0 18 8 1 0 16 11 1 0 1 54 1 0 1 55 1 0 1 56 1 0 5 57 1 0 6 58 1 0 6 59 1 0 7 60 1 6 8 61 1 1 9 62 1 0 9 63 1 0 10 64 1 0 12 65 1 0 12 66 1 0 13 67 1 6 14 68 1 0 14 69 1 0 15 70 1 0 15 71 1 0 17 72 1 0 17 73 1 0 17 74 1 0 18 75 1 6 19 76 1 0 19 77 1 0 20 78 1 0 20 79 1 0 22 80 1 0 22 81 1 0 22 82 1 0 24 83 1 6 25 84 1 1 26 85 1 6 27 86 1 1 28 87 1 6 29 88 1 0 29 89 1 0 30 90 1 0 33 91 1 1 34 92 1 6 35 93 1 1 36 94 1 6 37 95 1 0 37 96 1 0 39 97 1 0 40 98 1 0 41 99 1 0 42100 1 0 44101 1 1 45102 1 6 46103 1 6 47104 1 1 48105 1 6 49106 1 0 49107 1 0 49108 1 0 51109 1 0 52110 1 0 53111 1 0 M END

Standard InCHIKey	OHKPPWRIPKRDGS-YSUNMYHASA-N
Standard InCHI	InChI=1S/C38H58O15/c1-16(40)21-7-8-22-20-6-5-18-13-19(9-11-37(18,3)23(20)10-12-38(21,22)4)50-36-33(53-35-30(46)28(44)26(42)17(2)49-35)31(47)32(25(14-39)51-36)52-34-29(45)27(43)24(41)15-48-34/h5,7,17,19-20,22-36,39,41-47H,6,8-15H2,1-4H3/t17-,19-,20-,22-,23-,24+,25+,26-,27-,28+,29+,30+,31-,32+,33+,34-,35-,36+,37-,38+/m0/s1
SMILES	CC(=O)C1=CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	754.38	Volume:	729.853 ? Van der Waals volume.
Dense:	1.034	LogP:	1.473 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.108 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.784 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	39.0
TPSA:	234.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	7.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.147	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.802	Fsp³:	0.868
MCE-18:	133.859 ? 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:	0.745	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.246	Promiscuous compounds:	0.168

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.338	MDCK Permeability:	-5.155
Pgp-inhibitor:	0.0	Pgp-substrate:	0.732
PAMPA:	0.981 ? 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):	0.005
20% Bioavailability (F20%):	0.051	30% Bioavailability (F30%):	0.815
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009	MRP1:	0.064
Plasma Protein Binding (PPB):	63.049%	Volume Distribution (VD):	-0.43
Fu:	31.832% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.047
BSEP inhibitor:	0.144

ADMET: Metabolism

CYP1A2-inhibitor:	0.495	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.01	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.909	CYP3A4-substrate:	0.997
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.314
HLM stability:	0.355 ? 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):

0.44

Half-life (T1/2):

2.559

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.091
Human Hepatotoxicity (H-HT):	0.45	Drug-induced Liver Injury (DILI):	0.828
AMES Toxicity:	0.821	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.024	Skin Sensitization:	0.999
Carcinogencity:	0.042	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.994
Hematotoxicity:	0.35	Drug-induced Nephrotoxicity:	0.598
Genotoxicity:	0.066	RPMI-8226 Immunitoxicity:	0.193
A549 Cytotoxicity:	0.482	Hek293 Cytotoxicity:	0.456
BCF:	0.891 ? 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:	3.363 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.872 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.98 ? 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
NPO1158	Isochrysis galbana	Species	Isochrysidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1158	Isochrysis galbana	Species	Isochrysidaceae	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 NPC50068 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	20215
0.1-0.2	25304
0.2-0.3	3115
0.3-0.4	1063
0.4-0.5	98
0.5-0.6	34
0.6-0.7	26
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
0.9	High Similarity	NPC165439
0.6893	Remote Similarity	NPC475333
0.6893	Remote Similarity	NPC224098
0.6893	Remote Similarity	NPC208383
0.6762	Remote Similarity	NPC249265
0.6667	Remote Similarity	NPC232054
0.6505	Remote Similarity	NPC475182
0.6408	Remote Similarity	NPC124677
0.6364	Remote Similarity	NPC94272
0.6339	Remote Similarity	NPC480556
0.6321	Remote Similarity	NPC486386
0.6286	Remote Similarity	NPC73243
0.6286	Remote Similarity	NPC244086
0.6286	Remote Similarity	NPC84956
0.6214	Remote Similarity	NPC470433
0.6214	Remote Similarity	NPC46190
0.6214	Remote Similarity	NPC171073
0.6204	Remote Similarity	NPC194207
0.6204	Remote Similarity	NPC22779
0.6204	Remote Similarity	NPC254255
0.6168	Remote Similarity	NPC247037
0.6154	Remote Similarity	NPC248746
0.6095	Remote Similarity	NPC42171
0.6058	Remote Similarity	NPC265275
0.6038	Remote Similarity	NPC480555
0.6038	Remote Similarity	NPC150372
0.6	Remote Similarity	NPC122819
0.5946	Remote Similarity	NPC23808
0.5946	Remote Similarity	NPC87998
0.5872	Remote Similarity	NPC269297
0.5872	Remote Similarity	NPC222202
0.5841	Remote Similarity	NPC308140
0.5841	Remote Similarity	NPC287885
0.5833	Remote Similarity	NPC308459
0.5728	Remote Similarity	NPC306991
0.5714	Remote Similarity	NPC218571
0.5714	Remote Similarity	NPC487615
0.5714	Remote Similarity	NPC480554
0.5614	Remote Similarity	NPC480553
0.5593	Remote Similarity	NPC224314
0.5568	Remote Similarity	NPC207617
0.5568	Remote Similarity	NPC607440
0.5536	Remote Similarity	NPC13193
0.5408	Remote Similarity	NPC486114
0.5392	Remote Similarity	NPC86020
0.537	Remote Similarity	NPC486388
0.5364	Remote Similarity	NPC274200
0.5268	Remote Similarity	NPC102016
0.5268	Remote Similarity	NPC95051
0.5248	Remote Similarity	NPC272015
0.5229	Remote Similarity	NPC98696
0.5229	Remote Similarity	NPC40440
0.5185	Remote Similarity	NPC470748
0.5179	Remote Similarity	NPC156789
0.513	Remote Similarity	NPC309278
0.5094	Remote Similarity	NPC600456
0.5046	Remote Similarity	NPC305423
0.5046	Remote Similarity	NPC113044
0.5046	Remote Similarity	NPC283829
0.5046	Remote Similarity	NPC161676
0.5045	Remote Similarity	NPC602423

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC50068 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7030
0.1-0.2	1981
0.2-0.3	127
0.3-0.4	10
0.4-0.5	1
0.5-0.6	0
0.6-0.7	1
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
0.6	Remote Similarity	NPD8449	Approved

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