NPASS Compound

Natural Product: NPC322529

Natural Product ID	NPC322529
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gigantrionenin
IUPAC Name	(2S)-2-methyl-4-[7-[(2R,5S)-5-[(Z,1S,4R,5R)-1,4,5-trihydroxyhenicos-8-enyl]oxolan-2-yl]heptyl]-2H-furan-5-one
Synonyms	Gigantrionenin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL501337
PubChem CID	5470005
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

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 109110 0 0 0 0 0 0 0 0999 V2000 -11.2685 -3.2660 2.6610 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9470 -1.9681 2.9750 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2830 -1.1755 4.0510 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8745 -0.7759 3.7702 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7275 0.0858 2.5402 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2502 0.4135 2.3936 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9578 1.2755 1.2113 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3444 0.6861 -0.1038 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6600 -0.5923 -0.4576 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1496 -0.4314 -0.5488 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7731 0.5867 -1.5854 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2484 0.6774 -1.6451 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8498 1.7043 -2.6594 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1273 1.4232 -3.7383 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7645 2.4425 -4.6942 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3754 2.7109 -5.0542 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3540 3.1491 -4.1041 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0753 2.1965 -2.9926 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3557 2.4086 -2.5547 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7560 1.5116 -1.4428 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6189 0.0473 -1.7677 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0789 -0.8230 -0.5929 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7822 -2.2636 -0.8396 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1412 -2.9347 -0.7236 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0505 -1.7697 -1.0097 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4503 -0.6638 -0.4119 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4800 -1.9583 -0.7352 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8584 -2.2836 0.6875 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3746 -2.4187 0.8157 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7065 -2.7330 2.2369 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2082 -2.8540 2.4132 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8794 -1.5402 2.0175 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3979 -0.3957 2.8466 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0663 0.8680 2.4037 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9515 1.0197 1.4367 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3493 2.4341 1.3385 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5923 3.0597 2.3487 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7917 2.1620 3.0359 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9999 2.4134 3.9975 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8173 2.5461 1.6725 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2539 -0.2564 -2.9484 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9520 2.2873 -1.9538 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4332 4.4623 -3.6430 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2231 -3.3231 3.0068 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2567 -3.3631 1.5400 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8396 -4.1404 3.0322 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9714 -2.2223 3.3558 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1049 -1.3266 2.0927 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8765 -0.2332 4.1700 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3086 -1.6802 5.0424 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2146 -1.6827 3.6939 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5087 -0.2283 4.6690 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2884 1.0205 2.7207 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1215 -0.3763 1.6354 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9910 1.0187 3.3064 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7165 -0.5466 2.3746 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8781 1.5440 1.2307 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5123 2.2432 1.3063 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4396 0.4954 -0.0749 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1683 1.4378 -0.9069 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0497 -0.9257 -1.4446 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8517 -1.3348 0.3397 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7375 -0.2062 0.4380 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7501 -1.4150 -0.8710 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2194 1.5720 -1.4627 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0736 0.2014 -2.6043 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8152 0.9598 -0.6661 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7882 -0.2749 -1.9546 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1602 2.7303 -2.5156 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8155 0.3904 -3.8762 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2167 3.4469 -4.3721 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3032 2.1805 -5.6717 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4336 3.5393 -5.8689 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9418 1.8526 -5.6968 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6659 3.2240 -4.7208 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1482 1.1199 -3.3644 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0690 2.2813 -3.3957 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4697 3.4598 -2.2205 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3022 1.7820 -0.4833 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8681 1.6674 -1.2843 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5025 -0.1140 -1.9051 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5994 -0.4096 0.3167 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3681 -2.3958 -1.8618 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0511 -2.6958 -0.1374 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2139 -3.7422 -1.4760 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3025 -3.3819 0.2677 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9557 -1.6002 -2.1249 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0316 -1.0707 -1.1148 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8399 -2.8083 -1.3860 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4262 -3.2095 1.0551 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5116 -1.4494 1.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8956 -1.5568 0.4055 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6899 -3.3074 0.1953 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2967 -2.0224 2.9602 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2993 -3.7379 2.5495 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6277 -3.6400 1.7656 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4053 -2.9961 3.4911 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8024 -1.2991 0.9620 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9680 -1.7141 2.2257 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3069 -0.2755 2.8826 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7223 -0.5970 3.9092 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2937 0.1658 0.8339 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1245 2.8696 0.3383 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3804 3.0884 0.8830 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2762 1.5404 1.7502 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9315 3.0293 2.6782 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9533 0.4179 -3.1013 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6203 1.9442 -1.1125 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3515 4.6125 -3.2800 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 7 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 2 3 14 15 1 0 15 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 25 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 34 35 2 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 36 40 1 0 21 41 1 0 18 42 1 0 17 43 1 0 26 22 1 0 38 34 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 0 2 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 5 53 1 0 5 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 8 59 1 0 8 60 1 0 9 61 1 0 9 62 1 0 10 63 1 0 10 64 1 0 11 65 1 0 11 66 1 0 12 67 1 0 12 68 1 0 13 69 1 0 14 70 1 0 15 71 1 0 15 72 1 0 16 73 1 0 16 74 1 0 17 75 1 0 18 76 1 0 19 77 1 0 19 78 1 0 20 79 1 0 20 80 1 0 21 81 1 0 22 82 1 0 23 83 1 0 23 84 1 0 24 85 1 0 24 86 1 0 25 87 1 0 27 88 1 0 27 89 1 0 28 90 1 0 28 91 1 0 29 92 1 0 29 93 1 0 30 94 1 0 30 95 1 0 31 96 1 0 31 97 1 0 32 98 1 0 32 99 1 0 33100 1 0 33101 1 0 35102 1 0 36103 1 0 40104 1 0 40105 1 0 40106 1 0 41107 1 0 42108 1 0 43109 1 0 M END

Standard InCHIKey	HASWAOYLTAODRS-VKJZEEHVSA-N
Standard InCHI	InChI=1S/C37H66O6/c1-3-4-5-6-7-8-9-10-11-12-13-14-18-21-24-33(38)34(39)26-27-35(40)36-28-25-32(43-36)23-20-17-15-16-19-22-31-29-30(2)42-37(31)41/h14,18,29-30,32-36,38-40H,3-13,15-17,19-28H2,1-2H3/b18-14-/t30-,32+,33+,34+,35-,36-/m0/s1
SMILES	CCCCCCCCCCCCC=CCCC(C(CCC(C1CCC(O1)CCCCCCCC2=CC(OC2=O)C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	606.49	Volume:	676.227 ? Van der Waals volume.
Dense:	0.897	LogP:	7.999 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.949 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.976 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	27.0	Rigid Bonds:	12.0
TPSA:	96.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	2.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.049	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.585	Fsp³:	0.865
MCE-18:	30.029 ? 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:	0.651	Fluc inhibitor:	0.048 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.044 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.564	Promiscuous compounds:	0.002

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.094	MDCK Permeability:	-4.776
Pgp-inhibitor:	0.0	Pgp-substrate:	0.3
PAMPA:	0.03 ? 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):	0.99
20% Bioavailability (F20%):	0.991	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.977
Plasma Protein Binding (PPB):	98.393%	Volume Distribution (VD):	1.056
Fu:	1.947% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.58
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.674
BSEP inhibitor:	0.831

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.984	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.067	CYP2D6-substrate:	0.667
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.995
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.986
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):

5.547

Half-life (T1/2):

1.265

ADMET: Toxicity

hERG Blockers:	0.688	hERG Blockers (10um):	0.935
Human Hepatotoxicity (H-HT):	0.548	Drug-induced Liver Injury (DILI):	0.022
AMES Toxicity:	0.047	Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.795	Skin Sensitization:	1.0
Carcinogencity:	0.045	Eye Corrosion:	0.001
Eye Irritation:	0.145	Respiratory Toxicity:	0.399
Drug-induced Neurotoxicity:	0.027	Ototoxicity:	0.94
Hematotoxicity:	0.013	Drug-induced Nephrotoxicity:	0.841
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.043
A549 Cytotoxicity:	0.812	Hek293 Cytotoxicity:	0.58
BCF:	0.928 ? 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:	5.12 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.602 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.706 ? 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
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	bark	n.a.	PMID[1479382]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[1479382]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791471]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614426]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9322367]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917277]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	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
ED50	3
GI50	59

Activity Type	# Activity
Cell line	62

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
NPT81	Cell line	A549	Homo sapiens	ED50	=	3.94	10'-3 ug/ml	PMID[1479382]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	8.06	ug ml-1	PMID[1479382]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	2.92	10'-3 ug/ml	PMID[1479382]
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	3908.41	nM	PubChem BioAssay data set
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	5046.61	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	1174.9	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	109.65	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	1706.08	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	2466.04	nM	PubChem BioAssay data set
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	3655.95	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	2172.7	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	1264.74	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	10000.0	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	13708.82	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	5559.04	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	1145.51	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	1986.09	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	2167.7	nM	PubChem BioAssay data set
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	1244.51	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	4102.04	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	3076.1	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	2642.41	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	18535.32	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	1832.31	nM	PubChem BioAssay data set
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	7177.94	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	2172.7	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	1406.05	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	3349.65	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	3917.42	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	7447.32	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	13867.56	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	15240.53	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	2654.61	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	10839.27	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	1306.17	nM	PubChem BioAssay data set
NPT457	Cell line	BT-549	Homo sapiens	GI50	n.a.	8.185	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	2238.72	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	17298.16	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	1725.84	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	7655.97	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	1870.68	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	3854.78	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	2971.67	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	4415.7	nM	PubChem BioAssay data set
NPT306	Cell line	PC-3	Homo sapiens	GI50	n.a.	2754.23	nM	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	2275.1	nM	PubChem BioAssay data set
NPT396	Cell line	T47D	Homo sapiens	GI50	n.a.	3427.68	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	2910.72	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	1348.96	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	15848.93	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	1931.97	nM	PubChem BioAssay data set
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	n.a.	883.08	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	3176.87	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	6208.69	nM	PubChem BioAssay data set
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	n.a.	3026.91	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	54.58	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	1438.8	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	2306.75	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	1482.52	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	2944.42	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	19364.22	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	2978.52	nM	PubChem BioAssay data set

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
-	Artemia	LC50	=	13.9	ug.mL-1	PMID[1479382]

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 NPC322529 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	17763
0.1-0.2	29153
0.2-0.3	2563
0.3-0.4	164
0.4-0.5	86
0.5-0.6	70
0.6-0.7	38
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9074	High Similarity	NPC253801
0.8868	High Similarity	NPC480082
0.8302	Intermediate Similarity	NPC329615
0.7778	Intermediate Similarity	NPC65930
0.7593	Intermediate Similarity	NPC241360
0.7593	Intermediate Similarity	NPC293136
0.7407	Intermediate Similarity	NPC607439
0.7288	Intermediate Similarity	NPC480081
0.7241	Intermediate Similarity	NPC320458
0.7069	Intermediate Similarity	NPC258068
0.7069	Intermediate Similarity	NPC476583
0.678	Remote Similarity	NPC231096
0.678	Remote Similarity	NPC475581
0.678	Remote Similarity	NPC62118
0.678	Remote Similarity	NPC107717
0.678	Remote Similarity	NPC488252
0.6562	Remote Similarity	NPC279267
0.6545	Remote Similarity	NPC329829
0.65	Remote Similarity	NPC132496
0.65	Remote Similarity	NPC606740
0.65	Remote Similarity	NPC608614
0.6441	Remote Similarity	NPC309211
0.6441	Remote Similarity	NPC329838
0.6441	Remote Similarity	NPC600188
0.6333	Remote Similarity	NPC473478
0.6333	Remote Similarity	NPC473651
0.6333	Remote Similarity	NPC66346
0.6296	Remote Similarity	NPC73310
0.6296	Remote Similarity	NPC473529
0.6296	Remote Similarity	NPC180363
0.6296	Remote Similarity	NPC94875
0.6296	Remote Similarity	NPC11332
0.6296	Remote Similarity	NPC145914
0.6296	Remote Similarity	NPC601174
0.6296	Remote Similarity	NPC601403
0.6296	Remote Similarity	NPC603568
0.6296	Remote Similarity	NPC604330
0.6296	Remote Similarity	NPC608300
0.6296	Remote Similarity	NPC611200
0.6296	Remote Similarity	NPC611571
0.623	Remote Similarity	NPC283085
0.623	Remote Similarity	NPC473995
0.619	Remote Similarity	NPC473520
0.6167	Remote Similarity	NPC20621
0.6167	Remote Similarity	NPC318963
0.6167	Remote Similarity	NPC605101
0.6102	Remote Similarity	NPC219652
0.6102	Remote Similarity	NPC473840
0.6034	Remote Similarity	NPC156804
0.5965	Remote Similarity	NPC25764
0.5965	Remote Similarity	NPC235809
0.5965	Remote Similarity	NPC39279
0.5965	Remote Similarity	NPC475159
0.5965	Remote Similarity	NPC39167
0.5965	Remote Similarity	NPC131002
0.5965	Remote Similarity	NPC292809
0.5965	Remote Similarity	NPC202055
0.5965	Remote Similarity	NPC473780
0.5965	Remote Similarity	NPC604521
0.5965	Remote Similarity	NPC606804
0.5965	Remote Similarity	NPC607425
0.5965	Remote Similarity	NPC608574
0.5902	Remote Similarity	NPC488250
0.5873	Remote Similarity	NPC233551
0.5873	Remote Similarity	NPC40376
0.5873	Remote Similarity	NPC21208
0.5873	Remote Similarity	NPC477014
0.5873	Remote Similarity	NPC477013
0.5849	Remote Similarity	NPC609415
0.5833	Remote Similarity	NPC25703
0.5806	Remote Similarity	NPC69082
0.5806	Remote Similarity	NPC488249
0.5738	Remote Similarity	NPC132940
0.5692	Remote Similarity	NPC91067
0.5667	Remote Similarity	NPC473156
0.5667	Remote Similarity	NPC488246
0.5667	Remote Similarity	NPC163093
0.5667	Remote Similarity	NPC144415
0.5667	Remote Similarity	NPC282815
0.5667	Remote Similarity	NPC600524
0.5667	Remote Similarity	NPC600956
0.5667	Remote Similarity	NPC608157
0.5667	Remote Similarity	NPC608355
0.5645	Remote Similarity	NPC20533
0.5645	Remote Similarity	NPC485250
0.5606	Remote Similarity	NPC477015
0.5574	Remote Similarity	NPC473671
0.5574	Remote Similarity	NPC475268
0.5574	Remote Similarity	NPC470400
0.5574	Remote Similarity	NPC77871
0.5574	Remote Similarity	NPC9678
0.5574	Remote Similarity	NPC319036
0.5574	Remote Similarity	NPC605867
0.549	Remote Similarity	NPC474705
0.5469	Remote Similarity	NPC169511
0.5469	Remote Similarity	NPC287164
0.5469	Remote Similarity	NPC234077
0.5424	Remote Similarity	NPC100921
0.5424	Remote Similarity	NPC477018
0.541	Remote Similarity	NPC610454
0.5397	Remote Similarity	NPC605396
0.5373	Remote Similarity	NPC473905
0.5312	Remote Similarity	NPC477012
0.5231	Remote Similarity	NPC120398
0.5231	Remote Similarity	NPC471567
0.5231	Remote Similarity	NPC488244
0.5161	Remote Similarity	NPC473649
0.5161	Remote Similarity	NPC134865
0.5161	Remote Similarity	NPC154097
0.5161	Remote Similarity	NPC103523
0.5161	Remote Similarity	NPC159750
0.5161	Remote Similarity	NPC73248
0.5161	Remote Similarity	NPC488627
0.5161	Remote Similarity	NPC480080
0.5161	Remote Similarity	NPC488631
0.5161	Remote Similarity	NPC470401
0.5161	Remote Similarity	NPC477011
0.5143	Remote Similarity	NPC482766
0.5079	Remote Similarity	NPC604764

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC322529 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6691
0.1-0.2	2392
0.2-0.3	67
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