NPASS Compound

Natural Product: NPC42598

Natural Product ID	NPC42598
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	27-Hydroxybullatacin
IUPAC Name	(2S)-4-[(2R,13R)-13-[(2R,5R)-5-[(2R,5R)-5-[(1S,4S)-1,4-dihydroxyundecyl]oxolan-2-yl]oxolan-2-yl]-2,13-dihydroxytridecyl]-2-methyl-2H-furan-5-one
Synonyms	27-Hydroxy Bullatacin; 27-Hydroxybullatacin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL452015
PubChem CID	10722779
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 111113 0 0 0 0 0 0 0 0999 V2000 -14.9050 1.5679 -1.1099 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7964 0.3655 -0.2170 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.3823 0.2583 0.2770 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3881 0.1051 -0.8660 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0110 0.0107 -0.2084 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9304 -0.1450 -1.2328 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5437 -0.2463 -0.6239 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2066 0.9797 0.1685 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8316 0.8783 0.7558 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7099 -0.2848 1.6745 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4058 -0.4746 2.3516 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2558 -0.6767 1.4139 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4445 -1.8966 0.5759 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0150 -1.4642 -0.8098 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4623 -0.0955 -0.5850 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0384 0.3936 0.5837 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9728 -0.1441 -0.5508 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3322 1.2107 -0.4177 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0375 0.7892 0.1576 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3177 -0.3772 0.9711 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4858 -0.9327 0.4414 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6483 -1.4965 1.1099 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9888 -1.2288 1.6394 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9025 -0.3276 0.9214 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2851 -0.7745 -0.4628 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9962 -2.0977 -0.4812 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2588 -2.1413 0.2820 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3267 -1.1484 -0.1835 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7206 -1.3901 -1.5997 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6573 -0.4551 -2.2149 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0082 -0.2008 -1.6562 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1336 0.4802 -0.3537 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5708 0.6383 0.1104 C 0 0 2 0 0 0 0 0 0 0 0 0 11.3448 1.4481 -0.8601 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7698 1.6244 -0.3941 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3571 1.1732 0.6957 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7680 1.5965 0.7308 C 0 0 1 0 0 0 0 0 0 0 0 0 14.9604 2.3361 -0.4342 O 0 0 0 0 0 0 0 0 0 0 0 0 13.7631 2.3672 -1.1326 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5608 2.9544 -2.2483 O 0 0 0 0 0 0 0 0 0 0 0 0 14.9602 2.4920 1.9421 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0725 -0.6533 0.2749 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0303 -2.4182 1.9998 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1775 0.6500 3.1659 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2268 2.1177 -0.6395 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.3711 1.4236 -2.0614 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.4901 2.4540 -0.5953 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.0056 1.7173 -1.3121 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.0714 -0.5539 -0.7722 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.4474 0.5172 0.6512 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2872 -0.6179 0.9576 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1128 1.1451 0.8622 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5863 -0.7872 -1.4646 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4098 1.0481 -1.4508 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0280 -0.9284 0.4055 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8500 0.8769 0.4532 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9630 0.7333 -1.9002 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0778 -1.0438 -1.8399 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8383 -0.3190 -1.4868 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4643 -1.1970 -0.0824 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9265 1.1077 1.0233 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1318 0.8723 -0.1074 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5786 1.8122 1.3368 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9800 -1.2572 1.2022 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5208 -0.1417 2.4613 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5214 -1.3322 3.0578 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3325 -0.7527 2.0585 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7223 -2.6740 0.9675 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4310 -2.3606 0.5996 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2666 -2.1895 -1.1851 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8689 -1.4791 -1.5252 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8530 0.5544 -1.4074 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6277 -0.5628 -1.5272 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2138 1.7446 -1.3589 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9070 1.7951 0.3026 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3823 1.6684 0.7983 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6703 0.6564 -0.7131 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5945 0.0312 2.0099 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6416 -2.0442 0.1329 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8486 -0.7766 2.6748 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5688 -2.1718 1.8789 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8161 -0.2068 1.5748 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4837 0.6872 0.8562 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3539 -0.9211 -1.0453 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8433 0.0402 -0.9432 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1292 -2.3999 -1.5335 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3106 -2.8507 -0.0399 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1060 -1.9954 1.3628 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7136 -3.1513 0.1667 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2268 -1.5191 0.4301 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1558 -0.1295 0.1252 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8092 -1.5755 -2.2501 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2248 -2.4242 -1.6050 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8622 -0.8681 -3.2748 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1239 0.5545 -2.4100 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5828 -1.1782 -1.5856 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6392 0.3631 -2.4266 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5034 0.1601 0.4718 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8174 1.5732 -0.5471 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5648 1.1386 1.1071 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9050 2.4644 -0.8974 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3502 1.0139 -1.8823 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8878 0.5733 1.4711 H 0 0 0 0 0 0 0 0 0 0 0 0 15.4824 0.7396 0.7450 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0046 3.0353 2.0901 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8230 3.1667 1.7677 H 0 0 0 0 0 0 0 0 0 0 0 0 15.1756 1.8349 2.8064 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3601 -1.2244 0.6760 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4516 -3.3069 1.8789 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3952 1.1293 2.8049 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2259 2.9415 -0.1262 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 1 0 14 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 22 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 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 37 41 1 0 33 42 1 0 22 43 1 0 11 44 1 0 8 45 1 0 16 12 1 0 21 17 1 0 39 35 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 4 53 1 0 4 54 1 0 5 55 1 0 5 56 1 0 6 57 1 0 6 58 1 0 7 59 1 0 7 60 1 0 8 61 1 1 9 62 1 0 9 63 1 0 10 64 1 0 10 65 1 0 11 66 1 1 12 67 1 1 13 68 1 0 13 69 1 0 14 70 1 0 14 71 1 0 15 72 1 6 17 73 1 6 18 74 1 0 18 75 1 0 19 76 1 0 19 77 1 0 20 78 1 1 22 79 1 6 23 80 1 0 23 81 1 0 24 82 1 0 24 83 1 0 25 84 1 0 25 85 1 0 26 86 1 0 26 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 1 34101 1 0 34102 1 0 36103 1 0 37104 1 1 41105 1 0 41106 1 0 41107 1 0 42108 1 0 43109 1 0 44110 1 0 45111 1 0 M END

Standard InCHIKey	AJWQQZIFWOFRRM-MKQHPUIBSA-N
Standard InCHI	InChI=1S/C37H66O8/c1-3-4-5-10-13-16-29(38)19-20-32(41)34-22-24-36(45-34)35-23-21-33(44-35)31(40)18-15-12-9-7-6-8-11-14-17-30(39)26-28-25-27(2)43-37(28)42/h25,27,29-36,38-41H,3-24,26H2,1-2H3/t27-,29-,30+,31+,32-,33+,34+,35+,36+/m0/s1
SMILES	CCCCCCC[C@@H](CC[C@@H]([C@H]1CC[C@@H](O1)[C@H]1CC[C@@H](O1)[C@@H](CCCCCCCCCC[C@H](CC1=C[C@@H](OC1=O)C)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.48	Volume:	687.887 ? Van der Waals volume.
Dense:	0.928	LogP:	4.238 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.288 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.506 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	25.0	Rigid Bonds:	16.0
TPSA:	125.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.063	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.952	Fsp³:	0.919
MCE-18:	45.07 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.884	Fluc inhibitor:	0.027 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.056 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.591	Promiscuous compounds:	0.332

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.208	MDCK Permeability:	-4.856
Pgp-inhibitor:	0.001	Pgp-substrate:	0.997
PAMPA:	0.634 ? 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):	0.0
20% Bioavailability (F20%):	0.843	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.875
Plasma Protein Binding (PPB):	93.609%	Volume Distribution (VD):	0.386
Fu:	5.098% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.532
OATP1B3 inhibitor:	0.963	BCRP inhibitor:	0.828
BSEP inhibitor:	0.857

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.586	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.004	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.991
HLM stability:	0.023 ? 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):

5.708

Half-life (T1/2):

1.129

ADMET: Toxicity

hERG Blockers:	0.656	hERG Blockers (10um):	0.829
Human Hepatotoxicity (H-HT):	0.719	Drug-induced Liver Injury (DILI):	0.279
AMES Toxicity:	0.312	Rat Oral Acute Toxicity:	0.123
Maximum Recommended Daily Dose:	0.964	Skin Sensitization:	1.0
Carcinogencity:	0.404	Eye Corrosion:	0.004
Eye Irritation:	0.393	Respiratory Toxicity:	0.987
Drug-induced Neurotoxicity:	0.116	Ototoxicity:	0.86
Hematotoxicity:	0.218	Drug-induced Nephrotoxicity:	0.961
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.125
A549 Cytotoxicity:	0.996	Hek293 Cytotoxicity:	0.593
BCF:	1.425 ? 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:	5.104 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.174 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.48 ? 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
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	stem wood	n.a.	DOI[10.1021/np100247r]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395501]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425140]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15568797]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	stem	Taipei Botanical Garden, Taipei, Taiwan, China	2006-MAR	PMID[20828184]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25499882]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584397]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599260]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6333	Annona glabra	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
IZ	15
ED50	6

Activity Type	# Activity
Cell line	16
Non-molecular	5

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
NPT137	Cell line	L1210	Mus musculus	IZ	=	700.0	Zone units	PMID[12828466]
NPT137	Cell line	L1210	Mus musculus	IZ	=	250.0	Zone units	PMID[9748375]
NPT730	Cell line	MC-38	Mus musculus	IZ	=	900.0	Zone units	PMID[9748375]
NPT730	Cell line	MC-38	Mus musculus	IZ	=	950.0	Zone units	PMID[10924166]
NPT393	Cell line	HCT-116	Homo sapiens	IZ	=	600.0	Zone units	PMID[22938093]
NPT404	Cell line	CCRF-CEM	Homo sapiens	IZ	=	0.0	Zone units	PMID[10924166]
NPT137	Cell line	L1210	Mus musculus	IZ	=	350.0	Zone units	PMID[24387683]
NPT137	Cell line	L1210	Mus musculus	IZ	=	150.0	Zone units	PMID[25625705]
NPT730	Cell line	MC-38	Mus musculus	IZ	=	750.0	Zone units	PMID[15387649]
NPT730	Cell line	MC-38	Mus musculus	IZ	=	600.0	Zone units	PMID[8691208]
NPT81	Cell line	A549	Homo sapiens	ED50	=	2.1	10'-3 ug/ml	PMID[8946745]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	7.8	10'-4 ug/ml	PMID[16933872]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	1.8	10'-5 ug/ml	PMID[8946745]
NPT376	Cell line	A498	Homo sapiens	ED50	=	3.1	10'-8 ug/ml	PMID[16933872]
NPT306	Cell line	PC-3	Homo sapiens	ED50	<	1.0	10'-9 ug/ml	PMID[25211032]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	<	1.0	10'-9 ug/ml	PMID[10650093]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IZ	=	100.0	Zone units	PMID[18975929]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IZ	=	700.0	Zone units	PMID[18975929]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IZ	=	400.0	Zone units	PMID[18975929]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IZ	=	550.0	Zone units	PMID[18975929]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IZ	=	500.0	Zone units	PMID[18975929]

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 salina	LC50	=	0.043	ug.mL-1	DOI[10.6019/CHEMBL1201861]

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 NPC42598 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	17053
0.1-0.2	30001
0.2-0.3	2509
0.3-0.4	64
0.4-0.5	25
0.5-0.6	24
0.6-0.7	54
0.7-0.8	0
0.8-0.85	21
0.85-0.9	11
0.9-0.95	15
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9556	High Similarity	NPC93794
0.9556	High Similarity	NPC473504
0.9556	High Similarity	NPC81778
0.9556	High Similarity	NPC40066
0.9333	High Similarity	NPC81045
0.9333	High Similarity	NPC39754
0.9333	High Similarity	NPC171135
0.9333	High Similarity	NPC61257
0.9333	High Similarity	NPC320569
0.9333	High Similarity	NPC133730
0.9333	High Similarity	NPC191929
0.9333	High Similarity	NPC100454
0.9333	High Similarity	NPC242364
0.9333	High Similarity	NPC172821
0.9333	High Similarity	NPC274446
0.9333	High Similarity	NPC485251
0.9333	High Similarity	NPC151403
0.9333	High Similarity	NPC261952
0.9333	High Similarity	NPC605171
0.8913	High Similarity	NPC232555
0.8913	High Similarity	NPC171174
0.8913	High Similarity	NPC114694
0.8913	High Similarity	NPC485248
0.8913	High Similarity	NPC142117
0.8913	High Similarity	NPC480249
0.8913	High Similarity	NPC485249
0.8913	High Similarity	NPC240695
0.8723	High Similarity	NPC488632
0.8696	High Similarity	NPC473669
0.8571	High Similarity	NPC602738
0.8478	Intermediate Similarity	NPC107986
0.8478	Intermediate Similarity	NPC223871
0.8478	Intermediate Similarity	NPC231009
0.8478	Intermediate Similarity	NPC103284
0.8478	Intermediate Similarity	NPC110710
0.8478	Intermediate Similarity	NPC1083
0.8478	Intermediate Similarity	NPC82795
0.8478	Intermediate Similarity	NPC286338
0.8478	Intermediate Similarity	NPC603931
0.8478	Intermediate Similarity	NPC604237
0.8367	Intermediate Similarity	NPC132940
0.8298	Intermediate Similarity	NPC488253
0.8298	Intermediate Similarity	NPC488251
0.8261	Intermediate Similarity	NPC606043
0.8235	Intermediate Similarity	NPC169511
0.8235	Intermediate Similarity	NPC287164
0.8235	Intermediate Similarity	NPC234077
0.82	Intermediate Similarity	NPC20533
0.8163	Intermediate Similarity	NPC280621
0.8163	Intermediate Similarity	NPC48338
0.8163	Intermediate Similarity	NPC488628
0.7959	Intermediate Similarity	NPC473649
0.7959	Intermediate Similarity	NPC473156
0.7959	Intermediate Similarity	NPC154097
0.7959	Intermediate Similarity	NPC159750
0.7959	Intermediate Similarity	NPC73248
0.7959	Intermediate Similarity	NPC282815
0.7959	Intermediate Similarity	NPC47937
0.7959	Intermediate Similarity	NPC470401
0.7959	Intermediate Similarity	NPC600956
0.7959	Intermediate Similarity	NPC610454
0.7925	Intermediate Similarity	NPC239517
0.78	Intermediate Similarity	NPC473671
0.78	Intermediate Similarity	NPC475268
0.78	Intermediate Similarity	NPC470400
0.78	Intermediate Similarity	NPC77871
0.78	Intermediate Similarity	NPC9678
0.78	Intermediate Similarity	NPC319036
0.78	Intermediate Similarity	NPC604764
0.78	Intermediate Similarity	NPC605867
0.7778	Intermediate Similarity	NPC91067
0.7755	Intermediate Similarity	NPC182383
0.7647	Intermediate Similarity	NPC178215
0.76	Intermediate Similarity	NPC134865
0.76	Intermediate Similarity	NPC103523
0.76	Intermediate Similarity	NPC488627
0.76	Intermediate Similarity	NPC488631
0.75	Intermediate Similarity	NPC20621
0.75	Intermediate Similarity	NPC473663
0.75	Intermediate Similarity	NPC473723
0.75	Intermediate Similarity	NPC475173
0.75	Intermediate Similarity	NPC318963
0.75	Intermediate Similarity	NPC488250
0.75	Intermediate Similarity	NPC605101
0.74	Intermediate Similarity	NPC156804
0.7358	Intermediate Similarity	NPC69082
0.7358	Intermediate Similarity	NPC488249
0.7358	Intermediate Similarity	NPC20339
0.7347	Intermediate Similarity	NPC25764
0.7347	Intermediate Similarity	NPC235809
0.7347	Intermediate Similarity	NPC39279
0.7347	Intermediate Similarity	NPC39167
0.7347	Intermediate Similarity	NPC292809
0.7347	Intermediate Similarity	NPC202055
0.7347	Intermediate Similarity	NPC606804
0.7347	Intermediate Similarity	NPC607425
0.7347	Intermediate Similarity	NPC608574
0.7333	Intermediate Similarity	NPC608138
0.7308	Intermediate Similarity	NPC473687
0.7308	Intermediate Similarity	NPC204686
0.7308	Intermediate Similarity	NPC219498
0.7308	Intermediate Similarity	NPC308412
0.7308	Intermediate Similarity	NPC134885
0.7308	Intermediate Similarity	NPC488247
0.7308	Intermediate Similarity	NPC210218
0.7308	Intermediate Similarity	NPC488248
0.7255	Intermediate Similarity	NPC477011
0.7115	Intermediate Similarity	NPC480079
0.7091	Intermediate Similarity	NPC89001
0.7091	Intermediate Similarity	NPC488623
0.7091	Intermediate Similarity	NPC488624
0.7091	Intermediate Similarity	NPC488629
0.7037	Intermediate Similarity	NPC473478
0.7037	Intermediate Similarity	NPC473651
0.7037	Intermediate Similarity	NPC66346
0.7	Intermediate Similarity	NPC100921
0.7	Intermediate Similarity	NPC475159
0.7	Intermediate Similarity	NPC131002
0.7	Intermediate Similarity	NPC473780
0.7	Intermediate Similarity	NPC477018
0.7	Intermediate Similarity	NPC604521
0.6939	Remote Similarity	NPC112685
0.6923	Remote Similarity	NPC600524
0.6923	Remote Similarity	NPC608355
0.6909	Remote Similarity	NPC231096
0.6909	Remote Similarity	NPC475581
0.6909	Remote Similarity	NPC120398
0.6909	Remote Similarity	NPC283085
0.6909	Remote Similarity	NPC62118
0.6909	Remote Similarity	NPC132496
0.6909	Remote Similarity	NPC107717
0.6909	Remote Similarity	NPC130359
0.6909	Remote Similarity	NPC488252
0.6909	Remote Similarity	NPC14901
0.6909	Remote Similarity	NPC471567
0.6909	Remote Similarity	NPC606740
0.6909	Remote Similarity	NPC608614
0.6852	Remote Similarity	NPC134807
0.6792	Remote Similarity	NPC219652
0.6792	Remote Similarity	NPC473840
0.6786	Remote Similarity	NPC233551
0.6786	Remote Similarity	NPC40376
0.6786	Remote Similarity	NPC21208
0.6727	Remote Similarity	NPC473707
0.6552	Remote Similarity	NPC488630
0.6552	Remote Similarity	NPC488625
0.6552	Remote Similarity	NPC488626
0.6545	Remote Similarity	NPC329838
0.6545	Remote Similarity	NPC485250
0.6545	Remote Similarity	NPC605396
0.6481	Remote Similarity	NPC25703
0.64	Remote Similarity	NPC73310
0.64	Remote Similarity	NPC473529
0.64	Remote Similarity	NPC180363
0.64	Remote Similarity	NPC94875
0.64	Remote Similarity	NPC11332
0.64	Remote Similarity	NPC145914
0.64	Remote Similarity	NPC601174
0.64	Remote Similarity	NPC601403
0.64	Remote Similarity	NPC603568
0.64	Remote Similarity	NPC604330
0.64	Remote Similarity	NPC608300
0.64	Remote Similarity	NPC611200
0.64	Remote Similarity	NPC611571
0.6316	Remote Similarity	NPC258068
0.6316	Remote Similarity	NPC473995
0.6316	Remote Similarity	NPC476583
0.6296	Remote Similarity	NPC163093
0.6271	Remote Similarity	NPC480081
0.625	Remote Similarity	NPC309211
0.625	Remote Similarity	NPC477010
0.6038	Remote Similarity	NPC329829
0.6	Remote Similarity	NPC473520
0.6	Remote Similarity	NPC488246
0.6	Remote Similarity	NPC480080
0.5932	Remote Similarity	NPC477014
0.5932	Remote Similarity	NPC477013
0.5902	Remote Similarity	NPC473905
0.5893	Remote Similarity	NPC241360
0.5893	Remote Similarity	NPC293136
0.5873	Remote Similarity	NPC482766
0.5873	Remote Similarity	NPC279267
0.5789	Remote Similarity	NPC473904
0.5714	Remote Similarity	NPC144415
0.5714	Remote Similarity	NPC607439
0.5714	Remote Similarity	NPC608157
0.5593	Remote Similarity	NPC480076
0.5593	Remote Similarity	NPC480077
0.5556	Remote Similarity	NPC480072
0.5517	Remote Similarity	NPC65930
0.5484	Remote Similarity	NPC280612
0.5424	Remote Similarity	NPC329615
0.5385	Remote Similarity	NPC477017
0.5385	Remote Similarity	NPC477016
0.5333	Remote Similarity	NPC11456
0.5333	Remote Similarity	NPC477012
0.5254	Remote Similarity	NPC480251
0.5254	Remote Similarity	NPC480250
0.5246	Remote Similarity	NPC488244

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC42598 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6511
0.1-0.2	2591
0.2-0.3	48
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