NPASS Compound

Natural Product: NPC132940

Natural Product ID	NPC132940
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Sid524794
IUPAC Name	(2S)-4-[(8R,11R)-8,11-dihydroxy-11-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]oxolan-2-yl]undecyl]-2-methyl-2H-furan-5-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL300675
PubChem CID	393467
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 110112 0 0 0 0 0 0 0 0999 V2000 14.0175 1.4015 -1.2706 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5144 0.1126 -0.6720 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3765 0.2607 0.8206 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8811 -0.9873 1.4740 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5173 -1.4360 0.9770 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5399 -0.3379 1.2610 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1201 -0.6806 0.8175 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0159 -0.9415 -0.6284 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6499 -1.2483 -1.1002 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6663 -0.1660 -1.1304 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3227 0.6151 0.0755 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2194 1.6263 -0.1922 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9215 1.1041 -0.6261 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2782 0.1373 0.3372 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1433 0.6897 1.7199 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6663 0.9782 1.8415 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2009 0.9050 0.4150 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2558 0.4912 0.3157 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5954 0.3245 -1.1191 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2920 -1.0039 -1.1871 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3312 -1.4704 0.2045 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6487 -1.7823 0.8244 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4313 -0.6671 1.3724 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9043 0.4148 0.5029 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8727 0.0170 -0.5742 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1400 -0.5900 -0.0112 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0772 -0.9761 -1.1317 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3441 -1.5800 -0.6122 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1328 -0.6524 0.2866 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5384 0.6090 -0.4138 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4102 0.3540 -1.6178 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7049 -0.3486 -1.2616 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4044 0.5675 -0.3043 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7546 0.2950 0.9351 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.4171 1.4706 1.5229 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.8533 1.0518 1.8305 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.4204 2.4371 0.5313 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.8141 1.9321 -0.6014 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.6615 2.5658 -1.6775 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2498 1.1908 -1.2311 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3460 -2.6029 -0.0602 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5408 -0.6456 0.9998 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9889 -0.1148 -0.1106 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9538 0.5522 -1.8818 O 0 0 0 0 0 0 0 0 0 0 0 0 13.9433 2.2556 -0.5824 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4927 1.6637 -2.2137 H 0 0 0 0 0 0 0 0 0 0 0 0 15.1056 1.3322 -1.5601 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4663 -0.0348 -1.0650 H 0 0 0 0 0 0 0 0 0 0 0 0 14.1521 -0.7510 -0.9394 H 0 0 0 0 0 0 0 0 0 0 0 0 14.4106 0.4786 1.2010 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7803 1.1547 1.0320 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5944 -1.8120 1.3615 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7418 -0.7484 2.5685 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5517 -1.7494 -0.0735 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2535 -2.3317 1.5950 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8418 0.6147 0.7666 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4873 -0.1334 2.3476 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4407 -0.0073 1.2827 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9319 -1.6958 1.3204 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4436 -0.0687 -1.2396 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7428 -1.7721 -0.9410 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7651 -1.7390 -2.1270 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1981 -2.1147 -0.5088 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8470 0.5439 -2.0230 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6982 -0.6808 -1.5170 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2152 1.3022 0.2819 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1042 -0.0288 0.9198 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6255 2.2632 -1.0356 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1580 2.3672 0.6580 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2437 2.0201 -0.7434 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8713 -0.7933 0.3654 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3882 -0.1110 2.4670 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7708 1.5694 1.9208 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1352 0.2210 2.4691 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5518 2.0138 2.2339 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3330 1.8775 -0.0543 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8511 1.3306 0.7744 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2862 0.3684 -1.7899 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2479 1.1658 -1.4365 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6137 -1.6604 -1.8199 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2319 -0.9767 -1.7504 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7653 -2.4642 0.2236 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4294 -2.4708 1.7013 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7821 -0.1753 2.1623 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2936 -1.0464 1.9623 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1377 1.0553 0.0343 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4857 1.1267 1.1658 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4852 -0.6596 -1.3437 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6876 0.1710 0.6104 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9630 -1.4479 0.6313 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6185 -1.7270 -1.8108 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3327 -0.0695 -1.7556 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0827 -2.4723 -0.0088 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9521 -1.9345 -1.4718 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5353 -0.4096 1.1632 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0235 -1.2015 0.6349 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6889 1.2204 -0.7362 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1278 1.2175 0.3023 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9108 -0.2934 -2.3687 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6705 1.3025 -2.1288 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2804 -0.4725 -2.2073 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4630 -1.3030 -0.7817 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5648 -0.6782 1.4282 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9016 1.7906 2.4582 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.3378 1.8645 2.3825 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.3505 0.7794 0.8805 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.8730 0.1386 2.4607 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1678 1.4939 -0.9674 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7751 -3.3796 0.3773 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2060 0.8394 -2.4592 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 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 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 2 0 34 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 38 39 2 0 25 40 1 0 22 41 1 0 21 42 1 0 17 43 1 0 13 44 1 0 43 14 1 0 42 18 1 0 38 33 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 0 2 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 0 5 55 1 0 6 56 1 0 6 57 1 0 7 58 1 0 7 59 1 0 8 60 1 0 8 61 1 0 9 62 1 0 9 63 1 0 10 64 1 0 10 65 1 0 11 66 1 0 11 67 1 0 12 68 1 0 12 69 1 0 13 70 1 6 14 71 1 1 15 72 1 0 15 73 1 0 16 74 1 0 16 75 1 0 17 76 1 6 18 77 1 1 19 78 1 0 19 79 1 0 20 80 1 0 20 81 1 0 21 82 1 6 22 83 1 1 23 84 1 0 23 85 1 0 24 86 1 0 24 87 1 0 25 88 1 6 26 89 1 0 26 90 1 0 27 91 1 0 27 92 1 0 28 93 1 0 28 94 1 0 29 95 1 0 29 96 1 0 30 97 1 0 30 98 1 0 31 99 1 0 31100 1 0 32101 1 0 32102 1 0 34103 1 0 35104 1 1 36105 1 0 36106 1 0 36107 1 0 40108 1 0 41109 1 0 44110 1 0 M END

Standard InCHIKey	FOSMCUOHRDBFRX-UOCXRWNNSA-N
Standard InCHI	InChI=1S/C37H66O7/c1-3-4-5-6-7-8-9-10-14-17-20-31(39)33-23-25-35(43-33)36-26-24-34(44-36)32(40)22-21-30(38)19-16-13-11-12-15-18-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3/t28-,30+,31+,32+,33+,34+,35+,36+/m0/s1
SMILES	CCCCCCCCCCCC[C@H]([C@H]1CC[C@H]([C@H]2CC[C@H]([C@@H](CC[C@@H](CCCCCCCC3=C[C@H](C)OC3=O)O)O)O2)O1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	622.48	Volume:	679.097 ? Van der Waals volume.
Dense:	0.917	LogP:	5.696 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.92 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.861 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	25.0	Rigid Bonds:	16.0
TPSA:	105.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.07	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.787	Fsp³:	0.919
MCE-18:	42.817 ? 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:	0.88	Fluc inhibitor:	0.051 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.085 ? 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:	0.587	Promiscuous compounds:	0.38

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.16	MDCK Permeability:	-4.84
Pgp-inhibitor:	0.006	Pgp-substrate:	0.988
PAMPA:	0.056 ? 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):	0.019
20% Bioavailability (F20%):	0.992	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.933
Plasma Protein Binding (PPB):	97.773%	Volume Distribution (VD):	0.778
Fu:	2.367% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.694
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.846
BSEP inhibitor:	0.932

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.578
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.227
CYP2C9-inhibitor:	0.198	CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.615
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.083 ? 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):

5.341

Half-life (T1/2):

1.226

ADMET: Toxicity

hERG Blockers:	0.579	hERG Blockers (10um):	0.88
Human Hepatotoxicity (H-HT):	0.693	Drug-induced Liver Injury (DILI):	0.197
AMES Toxicity:	0.467	Rat Oral Acute Toxicity:	0.234
Maximum Recommended Daily Dose:	0.933	Skin Sensitization:	1.0
Carcinogencity:	0.493	Eye Corrosion:	0.031
Eye Irritation:	0.605	Respiratory Toxicity:	0.979
Drug-induced Neurotoxicity:	0.108	Ototoxicity:	0.712
Hematotoxicity:	0.208	Drug-induced Nephrotoxicity:	0.932
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.102
A549 Cytotoxicity:	0.996	Hek293 Cytotoxicity:	0.52
BCF:	1.054 ? 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:	4.969 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.281 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.082 ? 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
NPO6886	Asimina longifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7494147]
NPO6886	Asimina longifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8627602]
NPO6886	Asimina longifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6886	Asimina longifolia	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	6
GI50	55

Activity Type	# Activity
Cell line	61

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	=	0.000493	ug ml-1	PMID[20516285]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	0.215	ug ml-1	PMID[20516285]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	0.0116	ug ml-1	PMID[20516285]
NPT376	Cell line	A498	Homo sapiens	ED50	=	0.0353	ug ml-1	PMID[20516285]
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	0.000242	ug ml-1	PMID[20516285]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	=	1.69e-07	ug ml-1	PMID[20516285]
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	3221.07	nM	PMID[22250891]
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	1901.08	nM	DOI[10.1039/C2MD20076G]
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	93.33	nM	DOI[10.6019/CHEMBL1201861]
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	20.14	nM	DOI[10.1007/s00044-012-0322-5]
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	562.34	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	2157.74	nM	PMID[12828466]
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	1256.03	nM	PMID[11063622]
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	3380.65	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	1678.8	nM	DrugMatrix in vitro pharmacology data
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	1383.57	nM	PMID[10869194]
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	1051.96	nM	PMID[25237727]
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	2523.48	nM	PMID[17190457]
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	1584.89	nM	PMID[20797868]
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	1840.77	nM	PMID[19715320]
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	1570.36	nM	PMID[18625769]
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	1291.22	nM	PMID[12699389]
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	1815.52	nM	PMID[25497963]
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	2133.04	nM	PMID[17958396]
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	1686.55	nM	DrugMatrix in vitro pharmacology data
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	1230.27	nM	PMID[15974609]
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	2618.18	nM	PMID[17452481]
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	2027.68	nM	Open TG-GATES in vivo data: Hematology
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	1213.39	nM	PMID[12088425]
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	1940.89	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	1435.49	nM	PMID[18541727]
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	1644.37	nM	PMID[10843569]
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	2233.57	nM	DOI[10.6019/CHEMBL1201861]
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	1196.74	nM	PMID[25062006]
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	1174.9	nM	PMID[25938459]
NPT457	Cell line	BT-549	Homo sapiens	GI50	n.a.	3.524	nM	DOI[10.6019/CHEMBL1201861]
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	1520.55	nM	PMID[18362191]
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	1348.96	nM	PMID[17765551]
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	1753.88	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	1233.1	nM	PMID[22321992]
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	2032.36	nM	PMID[18183025]
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	1552.39	nM	PMID[10869208]
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	1099.01	nM	PMID[10560729]
NPT306	Cell line	PC-3	Homo sapiens	GI50	n.a.	1545.25	nM	PMID[19258268]
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	1150.8	nM	PMID[22180047]
NPT396	Cell line	T47D	Homo sapiens	GI50	n.a.	3404.08	nM	PMID[16792422]
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	1078.95	nM	DrugMatrix in vivo data: Biochemistry
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	1020.94	nM	PMID[19583252]
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	2673.01	nM	PMID[9873511]
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	n.a.	1774.19	nM	PMID[19223615]
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	1256.03	nM	PMID[20014752]
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	1651.96	nM	PMID[20614907]
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	n.a.	2177.71	nM	PMID[25127465]
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	2404.36	nM	PMID[20194693]
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	135.52	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	1088.93	nM	PMID[23571415]
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	1761.98	nM	PMID[25316316]
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	1667.25	nM	PMID[19700322]
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	1629.3	nM	PMID[9784152]
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	2123.24	nM	PMID[18973387]
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	1857.8	nM	PMID[25136911]

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	=	4.58	ug.mL-1	PMID[20516285]

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 NPC132940 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	16721
0.1-0.2	29992
0.2-0.3	2841
0.3-0.4	71
0.4-0.5	30
0.5-0.6	42
0.6-0.7	46
0.7-0.8	0
0.8-0.85	9
0.85-0.9	16
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9783	High Similarity	NPC20533
0.9556	High Similarity	NPC473156
0.9556	High Similarity	NPC282815
0.9556	High Similarity	NPC600956
0.9348	High Similarity	NPC473671
0.9348	High Similarity	NPC475268
0.9348	High Similarity	NPC470400
0.9348	High Similarity	NPC77871
0.9348	High Similarity	NPC9678
0.9348	High Similarity	NPC319036
0.9348	High Similarity	NPC605867
0.913	High Similarity	NPC610454
0.8913	High Similarity	NPC156804
0.8889	High Similarity	NPC25764
0.8889	High Similarity	NPC235809
0.8889	High Similarity	NPC39279
0.8889	High Similarity	NPC39167
0.8889	High Similarity	NPC292809
0.8889	High Similarity	NPC202055
0.8889	High Similarity	NPC606804
0.8889	High Similarity	NPC607425
0.8889	High Similarity	NPC608574
0.8723	High Similarity	NPC473649
0.8723	High Similarity	NPC154097
0.8723	High Similarity	NPC159750
0.8723	High Similarity	NPC73248
0.8723	High Similarity	NPC470401
0.8542	High Similarity	NPC604764
0.8478	Intermediate Similarity	NPC475159
0.8478	Intermediate Similarity	NPC131002
0.8478	Intermediate Similarity	NPC473780
0.8478	Intermediate Similarity	NPC604521
0.8367	Intermediate Similarity	NPC42598
0.8235	Intermediate Similarity	NPC120398
0.8235	Intermediate Similarity	NPC471567
0.8163	Intermediate Similarity	NPC219652
0.8163	Intermediate Similarity	NPC473840
0.7959	Intermediate Similarity	NPC93794
0.7959	Intermediate Similarity	NPC473504
0.7959	Intermediate Similarity	NPC81778
0.7959	Intermediate Similarity	NPC40066
0.7843	Intermediate Similarity	NPC329838
0.7843	Intermediate Similarity	NPC485250
0.7843	Intermediate Similarity	NPC605396
0.7826	Intermediate Similarity	NPC73310
0.7826	Intermediate Similarity	NPC473529
0.7826	Intermediate Similarity	NPC180363
0.7826	Intermediate Similarity	NPC94875
0.7826	Intermediate Similarity	NPC11332
0.7826	Intermediate Similarity	NPC145914
0.7826	Intermediate Similarity	NPC601174
0.7826	Intermediate Similarity	NPC601403
0.7826	Intermediate Similarity	NPC603568
0.7826	Intermediate Similarity	NPC604330
0.7826	Intermediate Similarity	NPC608300
0.7826	Intermediate Similarity	NPC611200
0.7826	Intermediate Similarity	NPC611571
0.78	Intermediate Similarity	NPC25703
0.7755	Intermediate Similarity	NPC81045
0.7755	Intermediate Similarity	NPC39754
0.7755	Intermediate Similarity	NPC171135
0.7755	Intermediate Similarity	NPC61257
0.7755	Intermediate Similarity	NPC320569
0.7755	Intermediate Similarity	NPC133730
0.7755	Intermediate Similarity	NPC191929
0.7755	Intermediate Similarity	NPC100454
0.7755	Intermediate Similarity	NPC242364
0.7755	Intermediate Similarity	NPC172821
0.7755	Intermediate Similarity	NPC274446
0.7755	Intermediate Similarity	NPC485251
0.7755	Intermediate Similarity	NPC151403
0.7755	Intermediate Similarity	NPC261952
0.7755	Intermediate Similarity	NPC605171
0.7736	Intermediate Similarity	NPC89001
0.7708	Intermediate Similarity	NPC100921
0.7708	Intermediate Similarity	NPC477018
0.76	Intermediate Similarity	NPC163093
0.76	Intermediate Similarity	NPC600524
0.76	Intermediate Similarity	NPC608355
0.7547	Intermediate Similarity	NPC258068
0.7547	Intermediate Similarity	NPC473995
0.7547	Intermediate Similarity	NPC476583
0.74	Intermediate Similarity	NPC232555
0.74	Intermediate Similarity	NPC171174
0.74	Intermediate Similarity	NPC114694
0.74	Intermediate Similarity	NPC485248
0.74	Intermediate Similarity	NPC142117
0.74	Intermediate Similarity	NPC480249
0.74	Intermediate Similarity	NPC485249
0.74	Intermediate Similarity	NPC240695
0.7347	Intermediate Similarity	NPC329829
0.7255	Intermediate Similarity	NPC488632
0.72	Intermediate Similarity	NPC473669
0.717	Intermediate Similarity	NPC602738
0.7143	Intermediate Similarity	NPC473520
0.7115	Intermediate Similarity	NPC241360
0.7115	Intermediate Similarity	NPC293136
0.7091	Intermediate Similarity	NPC477014
0.7091	Intermediate Similarity	NPC477013
0.7018	Intermediate Similarity	NPC473905
0.7	Intermediate Similarity	NPC107986
0.7	Intermediate Similarity	NPC223871
0.7	Intermediate Similarity	NPC231009
0.7	Intermediate Similarity	NPC103284
0.7	Intermediate Similarity	NPC110710
0.7	Intermediate Similarity	NPC1083
0.7	Intermediate Similarity	NPC82795
0.7	Intermediate Similarity	NPC286338
0.7	Intermediate Similarity	NPC603931
0.7	Intermediate Similarity	NPC604237
0.6923	Remote Similarity	NPC144415
0.6923	Remote Similarity	NPC607439
0.6923	Remote Similarity	NPC608157
0.6909	Remote Similarity	NPC169511
0.6909	Remote Similarity	NPC287164
0.6909	Remote Similarity	NPC234077
0.6863	Remote Similarity	NPC488253
0.6863	Remote Similarity	NPC488251
0.6852	Remote Similarity	NPC309211
0.6852	Remote Similarity	NPC477010
0.68	Remote Similarity	NPC606043
0.6792	Remote Similarity	NPC280621
0.6792	Remote Similarity	NPC48338
0.6792	Remote Similarity	NPC488628
0.6667	Remote Similarity	NPC239517
0.6667	Remote Similarity	NPC65930
0.6604	Remote Similarity	NPC47937
0.6604	Remote Similarity	NPC477011
0.6552	Remote Similarity	NPC91067
0.6552	Remote Similarity	NPC280612
0.6545	Remote Similarity	NPC329615
0.6415	Remote Similarity	NPC182383
0.6364	Remote Similarity	NPC178215
0.6333	Remote Similarity	NPC473663
0.6333	Remote Similarity	NPC473723
0.6333	Remote Similarity	NPC475173
0.6296	Remote Similarity	NPC134865
0.6296	Remote Similarity	NPC103523
0.6296	Remote Similarity	NPC488627
0.6296	Remote Similarity	NPC488631
0.625	Remote Similarity	NPC20621
0.625	Remote Similarity	NPC318963
0.625	Remote Similarity	NPC488250
0.625	Remote Similarity	NPC605101
0.625	Remote Similarity	NPC609415
0.614	Remote Similarity	NPC69082
0.614	Remote Similarity	NPC488249
0.614	Remote Similarity	NPC20339
0.6071	Remote Similarity	NPC473687
0.6071	Remote Similarity	NPC204686
0.6071	Remote Similarity	NPC219498
0.6071	Remote Similarity	NPC308412
0.6071	Remote Similarity	NPC134885
0.6071	Remote Similarity	NPC488247
0.6071	Remote Similarity	NPC210218
0.6071	Remote Similarity	NPC488248
0.5932	Remote Similarity	NPC488623
0.5932	Remote Similarity	NPC320458
0.5932	Remote Similarity	NPC488624
0.5932	Remote Similarity	NPC480082
0.5932	Remote Similarity	NPC488629
0.5918	Remote Similarity	NPC608138
0.5902	Remote Similarity	NPC253801
0.5902	Remote Similarity	NPC477015
0.5893	Remote Similarity	NPC480079
0.5873	Remote Similarity	NPC477017
0.5873	Remote Similarity	NPC477016
0.5862	Remote Similarity	NPC473478
0.5862	Remote Similarity	NPC473651
0.5862	Remote Similarity	NPC66346
0.5862	Remote Similarity	NPC477012
0.5763	Remote Similarity	NPC231096
0.5763	Remote Similarity	NPC475581
0.5763	Remote Similarity	NPC283085
0.5763	Remote Similarity	NPC62118
0.5763	Remote Similarity	NPC132496
0.5763	Remote Similarity	NPC107717
0.5763	Remote Similarity	NPC130359
0.5763	Remote Similarity	NPC488252
0.5763	Remote Similarity	NPC14901
0.5763	Remote Similarity	NPC606740
0.5763	Remote Similarity	NPC608614
0.5738	Remote Similarity	NPC322529
0.569	Remote Similarity	NPC134807
0.5667	Remote Similarity	NPC233551
0.5667	Remote Similarity	NPC40376
0.5667	Remote Similarity	NPC21208
0.566	Remote Similarity	NPC112685
0.5593	Remote Similarity	NPC473707
0.5556	Remote Similarity	NPC480072
0.5484	Remote Similarity	NPC488630
0.5484	Remote Similarity	NPC488625
0.5484	Remote Similarity	NPC488626
0.5333	Remote Similarity	NPC480076
0.5333	Remote Similarity	NPC480077
0.5238	Remote Similarity	NPC480081
0.5111	Remote Similarity	NPC84038
0.5082	Remote Similarity	NPC139418

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC132940 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6503
0.1-0.2	2590
0.2-0.3	57
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