NPASS Compound

Natural Product: NPC473707

Natural Product ID	NPC473707
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cis-Annonacin Formal
IUPAC Name	(2S)-4-[(2R,8R)-11-[(1S,2S,6R,7S)-2-dodecyl-3,5,10-trioxabicyclo[5.2.1]decan-6-yl]-2,8-dihydroxyundecyl]-2-methyl-2H-furan-5-one
Synonyms	Cis-Annonacin Formal
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL449783
PubChem CID	44584240
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 104106 0 0 0 0 0 0 0 0999 V2000 -12.6142 -0.8359 -2.1585 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3107 -1.4055 -2.7378 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3949 -0.2138 -2.8919 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0482 -0.5433 -3.4484 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2510 -1.5077 -2.6416 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9585 -1.0906 -1.2509 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2014 0.1707 -1.0651 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8449 0.2272 -1.6788 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8926 -0.8155 -1.1894 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6139 -0.8074 0.2704 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0250 0.4674 0.8101 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7298 0.7535 0.1451 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0360 2.0212 0.6031 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8774 2.0674 -0.1546 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3540 2.0083 0.3727 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6970 1.1665 1.3602 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9043 1.5782 2.6459 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0428 2.5939 3.1826 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7152 3.0262 2.0756 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6988 2.0008 1.9716 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4137 2.4401 3.1727 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1543 2.1995 4.0907 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0765 0.3635 3.5186 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2270 -0.5200 3.1237 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5082 0.2213 3.2013 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6634 -0.7079 2.8259 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9090 0.1822 2.9528 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1183 -0.5702 2.6200 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2874 -1.2407 1.3419 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2808 -0.4506 0.1042 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0792 0.2640 -0.3364 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2693 1.0216 -1.6104 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6095 0.3382 -2.8564 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8344 -0.4294 -2.9962 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9431 -1.7289 -3.3235 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3526 -2.1113 -3.3553 C 0 0 1 0 0 0 0 0 0 0 0 0 10.0554 -0.9414 -3.0535 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1934 0.1161 -2.8121 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4720 1.3071 -2.4990 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6740 -3.1782 -2.3152 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2047 2.0481 -1.2945 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7115 -1.7767 3.6862 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.2493 -1.6083 -1.7202 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2875 -0.0760 -1.3904 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0850 -0.2436 -2.9643 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8862 -2.1564 -2.0345 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5542 -1.8115 -3.7241 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3518 0.2958 -1.9078 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8992 0.4372 -3.6673 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2359 -1.0481 -4.4434 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4384 0.3370 -3.6814 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8428 -2.4587 -2.5812 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3328 -1.7680 -3.1751 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3286 -1.9122 -0.7955 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8522 -1.0526 -0.5911 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7548 1.0771 -1.4161 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1332 0.3324 0.0513 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3880 1.2318 -1.5425 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9061 0.0970 -2.7940 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3776 -1.8071 -1.4173 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9405 -0.7171 -1.7461 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8877 -1.6514 0.4551 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5175 -1.1027 0.8795 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6924 1.3427 0.6383 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8209 0.3220 1.8918 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8277 0.7944 -0.9792 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9793 -0.0697 0.3224 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7247 2.8660 0.3399 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9576 1.5690 -0.5109 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8934 3.0121 0.4110 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8883 2.0955 2.6475 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4639 3.5063 3.6173 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3628 0.9858 2.2383 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2151 1.8339 3.5738 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5932 3.5397 3.2032 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2088 1.1281 4.3091 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2402 2.8512 4.9597 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1861 -0.3009 3.5135 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3109 0.6984 4.5730 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1939 -1.4051 3.8275 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0494 -0.9462 2.0903 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6970 0.6040 4.2104 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4963 1.0626 2.4766 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5300 -0.9830 1.7803 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9744 0.4587 4.0792 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6964 1.1357 2.4889 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9979 0.1608 2.8159 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2706 -1.3076 3.5009 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6216 -2.1628 1.2396 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3260 -1.7434 1.3809 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0944 0.3457 0.2342 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6084 -1.1326 -0.7312 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1887 -0.4430 -0.4515 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6624 1.0202 0.3887 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3054 1.6126 -1.7461 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7163 -0.3429 -3.1121 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5513 1.0937 -3.7072 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0973 -2.3497 -3.5218 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6188 -2.5186 -4.3607 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3763 -2.7341 -1.5836 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7548 -3.4519 -1.7460 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1193 -4.0626 -2.7960 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9376 2.4355 -0.4341 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7281 -2.6228 3.1354 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 17 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 2 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 36 40 1 0 32 41 1 0 26 42 1 0 20 13 1 0 38 34 1 0 22 18 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 2 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 0 5 53 1 0 6 54 1 0 6 55 1 0 7 56 1 0 7 57 1 0 8 58 1 0 8 59 1 0 9 60 1 0 9 61 1 0 10 62 1 0 10 63 1 0 11 64 1 0 11 65 1 0 12 66 1 0 12 67 1 0 13 68 1 1 15 69 1 0 15 70 1 0 17 71 1 6 18 72 1 1 20 73 1 1 21 74 1 0 21 75 1 0 22 76 1 0 22 77 1 0 23 78 1 0 23 79 1 0 24 80 1 0 24 81 1 0 25 82 1 0 25 83 1 0 26 84 1 6 27 85 1 0 27 86 1 0 28 87 1 0 28 88 1 0 29 89 1 0 29 90 1 0 30 91 1 0 30 92 1 0 31 93 1 0 31 94 1 0 32 95 1 6 33 96 1 0 33 97 1 0 35 98 1 0 36 99 1 6 40100 1 0 40101 1 0 40102 1 0 41103 1 0 42104 1 0 M END

Standard InCHIKey	CVTBDMFBFBIITE-RLWOUWICSA-N
Standard InCHI	InChI=1S/C35H62O7/c1-3-4-5-6-7-8-9-10-11-15-20-31-33-22-23-34(42-33)32(40-26-39-31)21-16-19-29(36)17-13-12-14-18-30(37)25-28-24-27(2)41-35(28)38/h24,27,29-34,36-37H,3-23,25-26H2,1-2H3/t27-,29+,30+,31-,32+,33-,34-/m0/s1
SMILES	CCCCCCCCCCCC[C@@H]1OCO[C@@H]([C@H]2O[C@H]1CC2)CCC[C@@H](CCCCC[C@H](CC1=C[C@@H](OC1=O)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.45	Volume:	644.505 ? Van der Waals volume.
Dense:	0.922	LogP:	4.878 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.703 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.25 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	23.0	Rigid Bonds:	17.0
TPSA:	94.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.092	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.454	Fsp³:	0.914
MCE-18:	40.299 ? 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:	0.816	Fluc inhibitor:	0.015 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.033 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.557	Promiscuous compounds:	0.332

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.147	MDCK Permeability:	-4.716
Pgp-inhibitor:	0.009	Pgp-substrate:	0.951
PAMPA:	0.002 ? 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):	0.031
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.993
Plasma Protein Binding (PPB):	95.895%	Volume Distribution (VD):	0.323
Fu:	3.161% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.012
OATP1B3 inhibitor:	0.665	BCRP inhibitor:	0.81
BSEP inhibitor:	0.969

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.157
CYP2C19-inhibitor:	0.006	CYP2C19-substrate:	0.02
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.065	CYP2D6-substrate:	0.998
CYP3A4-inhibitor:	0.33	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.11
HLM stability:	0.033 ? 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):

5.364

Half-life (T1/2):

0.941

ADMET: Toxicity

hERG Blockers:	0.499	hERG Blockers (10um):	0.806
Human Hepatotoxicity (H-HT):	0.709	Drug-induced Liver Injury (DILI):	0.227
AMES Toxicity:	0.456	Rat Oral Acute Toxicity:	0.156
Maximum Recommended Daily Dose:	0.944	Skin Sensitization:	1.0
Carcinogencity:	0.585	Eye Corrosion:	0.038
Eye Irritation:	0.635	Respiratory Toxicity:	0.976
Drug-induced Neurotoxicity:	0.141	Ototoxicity:	0.752
Hematotoxicity:	0.304	Drug-induced Nephrotoxicity:	0.964
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.158
A549 Cytotoxicity:	0.997	Hek293 Cytotoxicity:	0.592
BCF:	1.057 ? 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:	5.041 ? 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:	4.462 ? 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
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473425]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975482]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7494150]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673926]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673935]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673936]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[8946744]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8991944]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[9584396]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26234	Annona muricata	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
Inhibition	1
IC50	3

Activity Type	# Activity
Cell line	3
Organism	1

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	IC50	=	0.079	ug.mL-1	PMID[19132934]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	2.6	ug.mL-1	PMID[19267453]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	2.1	ug.mL-1	PMID[25906087]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	22.0	%	PMID[8759171]

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 NPC473707 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	15839
0.1-0.2	31218
0.2-0.3	2505
0.3-0.4	88
0.4-0.5	52
0.5-0.6	92
0.6-0.7	57
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	Natural Product ID
0.7544	Intermediate Similarity	NPC473663
0.7544	Intermediate Similarity	NPC473723
0.7544	Intermediate Similarity	NPC475173
0.717	Intermediate Similarity	NPC480079
0.7021	Intermediate Similarity	NPC608138
0.6981	Remote Similarity	NPC93794
0.6981	Remote Similarity	NPC473504
0.6981	Remote Similarity	NPC81778
0.6981	Remote Similarity	NPC40066
0.6792	Remote Similarity	NPC81045
0.6792	Remote Similarity	NPC39754
0.6792	Remote Similarity	NPC171135
0.6792	Remote Similarity	NPC61257
0.6792	Remote Similarity	NPC320569
0.6792	Remote Similarity	NPC133730
0.6792	Remote Similarity	NPC191929
0.6792	Remote Similarity	NPC100454
0.6792	Remote Similarity	NPC242364
0.6792	Remote Similarity	NPC172821
0.6792	Remote Similarity	NPC274446
0.6792	Remote Similarity	NPC485251
0.6792	Remote Similarity	NPC151403
0.6792	Remote Similarity	NPC261952
0.6792	Remote Similarity	NPC605171
0.6727	Remote Similarity	NPC42598
0.6667	Remote Similarity	NPC169511
0.6667	Remote Similarity	NPC287164
0.6667	Remote Similarity	NPC234077
0.6607	Remote Similarity	NPC602738
0.6481	Remote Similarity	NPC182383
0.6415	Remote Similarity	NPC107986
0.6415	Remote Similarity	NPC223871
0.6415	Remote Similarity	NPC231009
0.6415	Remote Similarity	NPC103284
0.6415	Remote Similarity	NPC110710
0.6415	Remote Similarity	NPC1083
0.6415	Remote Similarity	NPC82795
0.6415	Remote Similarity	NPC286338
0.6415	Remote Similarity	NPC603931
0.6415	Remote Similarity	NPC604237
0.6364	Remote Similarity	NPC47937
0.6333	Remote Similarity	NPC91067
0.6296	Remote Similarity	NPC488253
0.6296	Remote Similarity	NPC473669
0.6296	Remote Similarity	NPC488251
0.6271	Remote Similarity	NPC488623
0.6271	Remote Similarity	NPC488624
0.6271	Remote Similarity	NPC488629
0.6226	Remote Similarity	NPC606043
0.6182	Remote Similarity	NPC232555
0.6182	Remote Similarity	NPC171174
0.6182	Remote Similarity	NPC114694
0.6182	Remote Similarity	NPC485248
0.6182	Remote Similarity	NPC142117
0.6182	Remote Similarity	NPC480249
0.6182	Remote Similarity	NPC485249
0.6182	Remote Similarity	NPC240695
0.6071	Remote Similarity	NPC488632
0.6066	Remote Similarity	NPC473520
0.6034	Remote Similarity	NPC20621
0.6034	Remote Similarity	NPC318963
0.6034	Remote Similarity	NPC605101
0.5932	Remote Similarity	NPC473478
0.5932	Remote Similarity	NPC473651
0.5932	Remote Similarity	NPC66346
0.5902	Remote Similarity	NPC239517
0.5862	Remote Similarity	NPC178215
0.5833	Remote Similarity	NPC231096
0.5833	Remote Similarity	NPC475581
0.5833	Remote Similarity	NPC283085
0.5833	Remote Similarity	NPC62118
0.5833	Remote Similarity	NPC107717
0.5833	Remote Similarity	NPC488252
0.5789	Remote Similarity	NPC473649
0.5789	Remote Similarity	NPC473156
0.5789	Remote Similarity	NPC134865
0.5789	Remote Similarity	NPC154097
0.5789	Remote Similarity	NPC488246
0.5789	Remote Similarity	NPC103523
0.5789	Remote Similarity	NPC159750
0.5789	Remote Similarity	NPC73248
0.5789	Remote Similarity	NPC282815
0.5789	Remote Similarity	NPC488627
0.5789	Remote Similarity	NPC480080
0.5789	Remote Similarity	NPC488631
0.5789	Remote Similarity	NPC470401
0.5789	Remote Similarity	NPC600956
0.5789	Remote Similarity	NPC610454
0.5763	Remote Similarity	NPC488250
0.5741	Remote Similarity	NPC112685
0.569	Remote Similarity	NPC280621
0.569	Remote Similarity	NPC473671
0.569	Remote Similarity	NPC475268
0.569	Remote Similarity	NPC470400
0.569	Remote Similarity	NPC77871
0.569	Remote Similarity	NPC48338
0.569	Remote Similarity	NPC9678
0.569	Remote Similarity	NPC319036
0.569	Remote Similarity	NPC488628
0.569	Remote Similarity	NPC604764
0.569	Remote Similarity	NPC605867
0.5667	Remote Similarity	NPC69082
0.5667	Remote Similarity	NPC488249
0.5667	Remote Similarity	NPC20339
0.5593	Remote Similarity	NPC473687
0.5593	Remote Similarity	NPC204686
0.5593	Remote Similarity	NPC219498
0.5593	Remote Similarity	NPC308412
0.5593	Remote Similarity	NPC134885
0.5593	Remote Similarity	NPC488247
0.5593	Remote Similarity	NPC132940
0.5593	Remote Similarity	NPC210218
0.5593	Remote Similarity	NPC488248
0.5574	Remote Similarity	NPC132496
0.5574	Remote Similarity	NPC606740
0.5574	Remote Similarity	NPC608614
0.5556	Remote Similarity	NPC480081
0.5517	Remote Similarity	NPC477011
0.55	Remote Similarity	NPC20533
0.5484	Remote Similarity	NPC233551
0.5484	Remote Similarity	NPC40376
0.5484	Remote Similarity	NPC21208
0.5323	Remote Similarity	NPC130359
0.5323	Remote Similarity	NPC473995
0.5323	Remote Similarity	NPC14901
0.5312	Remote Similarity	NPC488630
0.5312	Remote Similarity	NPC488625
0.5312	Remote Similarity	NPC488626
0.5303	Remote Similarity	NPC488245
0.5263	Remote Similarity	NPC25764
0.5263	Remote Similarity	NPC235809
0.5263	Remote Similarity	NPC100921
0.5263	Remote Similarity	NPC39279
0.5263	Remote Similarity	NPC475159
0.5263	Remote Similarity	NPC39167
0.5263	Remote Similarity	NPC131002
0.5263	Remote Similarity	NPC292809
0.5263	Remote Similarity	NPC202055
0.5263	Remote Similarity	NPC473780
0.5263	Remote Similarity	NPC477018
0.5263	Remote Similarity	NPC604521
0.5263	Remote Similarity	NPC606804
0.5263	Remote Similarity	NPC607425
0.5263	Remote Similarity	NPC608574
0.5246	Remote Similarity	NPC134807
0.5238	Remote Similarity	NPC89001
0.5224	Remote Similarity	NPC482766
0.5224	Remote Similarity	NPC279267
0.5085	Remote Similarity	NPC156804
0.5079	Remote Similarity	NPC120398
0.5079	Remote Similarity	NPC258068
0.5079	Remote Similarity	NPC471567
0.5079	Remote Similarity	NPC488244
0.5079	Remote Similarity	NPC476583

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473707 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6596
0.1-0.2	2502
0.2-0.3	52
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