NPASS Compound

Natural Product: NPC566125

Natural Product ID	NPC566125
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DTXSID20862061
IUPAC Name	2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,26,30-dodecaene
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 98 97 0 0 0 0 0 0 0 0999 V2000 -12.9261 3.5449 -0.7586 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.6076 2.7245 0.4228 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8392 3.3907 1.5339 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9398 1.4623 0.6037 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.7008 0.6091 -0.3395 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8552 -0.5840 -0.7803 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6611 -0.1279 -1.5373 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9212 0.6124 -2.8352 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4060 -0.3233 -1.1814 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3847 0.2039 -2.0682 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1076 0.0575 -1.7835 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1385 0.6030 -2.7119 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6457 1.2846 -3.9370 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8698 0.5178 -2.5283 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3009 -0.1361 -1.3624 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9637 -0.2199 -1.2170 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4347 -0.8759 -0.0417 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4374 -1.3811 0.9552 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1639 -1.0415 0.2005 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1459 -0.5854 -0.6961 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1614 -0.7279 -0.4797 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7435 -1.3462 0.6701 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0328 -1.5213 0.9080 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3259 -2.2002 2.2208 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0741 -1.1984 0.0017 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3405 -1.2821 0.0762 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1594 -1.7463 1.1585 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5009 -1.7675 0.9886 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0518 -1.3236 -0.2968 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3700 -2.2367 2.0635 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3389 -1.2359 2.6154 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2697 -0.6367 1.6704 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5945 -0.7610 1.6945 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2104 -1.5785 2.7758 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4272 -0.1522 0.6552 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4144 0.8810 1.1449 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1846 1.4127 -0.0345 C 0 0 0 0 0 0 0 0 0 0 0 0 14.4969 1.3791 -0.0294 C 0 0 0 0 0 0 0 0 0 0 0 0 15.2130 0.8227 1.1387 C 0 0 0 0 0 0 0 0 0 0 0 0 15.2165 1.8993 -1.2224 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9777 4.6168 -0.4474 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1479 3.4649 -1.5441 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.9054 3.2944 -1.2005 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4304 3.2114 2.4629 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8528 2.9127 1.6821 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7717 4.4758 1.3611 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6501 0.9352 1.5385 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.6534 0.2278 0.0432 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.9215 1.1942 -1.2557 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5253 -1.1361 0.1173 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5035 -1.2507 -1.4090 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9866 0.7410 -3.0218 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4508 -0.0203 -3.6364 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4511 1.6093 -2.8278 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1874 -0.8565 -0.2698 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6511 0.7237 -2.9915 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8623 -0.4613 -0.8713 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3131 2.1122 -3.6184 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2039 0.4916 -4.4945 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8695 1.6475 -4.6055 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1615 0.9411 -3.2550 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8964 -0.5683 -0.5838 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3277 0.2192 -1.9928 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0737 -2.1453 0.4768 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0873 -0.5447 1.2670 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8932 -1.7129 1.8496 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9027 -1.5561 1.1386 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4291 -0.0856 -1.6260 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8627 -0.3362 -1.2329 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0614 -1.7357 1.4742 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3447 -2.4765 2.7192 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8065 -1.5301 2.9409 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8531 -3.1407 2.0551 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6935 -0.7914 -0.9884 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9007 -0.9164 -0.8592 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8334 -2.0802 2.1219 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9117 -0.2631 -0.4612 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1145 -1.6712 -0.4337 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5326 -1.8684 -1.1488 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9277 -3.1743 1.7749 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7444 -2.5733 2.9463 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7987 -0.4402 3.1790 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9776 -1.8107 3.3618 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8836 0.0067 0.8746 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2020 -1.0894 3.7500 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7551 -2.6035 2.8322 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2921 -1.7844 2.5359 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0068 -0.9276 0.0863 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7882 0.3323 -0.1214 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9127 1.7626 1.5921 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0707 0.4403 1.9117 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5835 1.8093 -0.8467 H 0 0 0 0 0 0 0 0 0 0 0 0 14.9109 -0.2218 1.3225 H 0 0 0 0 0 0 0 0 0 0 0 0 16.2951 0.7894 0.8883 H 0 0 0 0 0 0 0 0 0 0 0 0 15.0410 1.4333 2.0564 H 0 0 0 0 0 0 0 0 0 0 0 0 16.0410 2.5872 -0.9333 H 0 0 0 0 0 0 0 0 0 0 0 0 14.5336 2.3410 -1.9639 H 0 0 0 0 0 0 0 0 0 0 0 0 15.7308 1.0358 -1.7517 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 2 3 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 2 3 9 10 1 0 10 11 2 3 11 12 1 0 12 13 1 0 12 14 2 3 14 15 1 0 15 16 2 3 16 17 1 0 17 18 1 0 17 19 2 3 19 20 1 0 20 21 2 3 21 22 1 0 22 23 2 3 23 24 1 0 23 25 1 0 25 26 2 3 26 27 1 0 27 28 2 3 28 29 1 0 28 30 1 0 30 31 1 0 31 32 1 0 32 33 2 3 33 34 1 0 33 35 1 0 35 36 1 0 36 37 1 0 37 38 2 3 38 39 1 0 38 40 1 0 1 41 1 0 1 42 1 0 1 43 1 0 3 44 1 0 3 45 1 0 3 46 1 0 4 47 1 0 5 48 1 0 5 49 1 0 6 50 1 0 6 51 1 0 8 52 1 0 8 53 1 0 8 54 1 0 9 55 1 0 10 56 1 0 11 57 1 0 13 58 1 0 13 59 1 0 13 60 1 0 14 61 1 0 15 62 1 0 16 63 1 0 18 64 1 0 18 65 1 0 18 66 1 0 19 67 1 0 20 68 1 0 21 69 1 0 22 70 1 0 24 71 1 0 24 72 1 0 24 73 1 0 25 74 1 0 26 75 1 0 27 76 1 0 29 77 1 0 29 78 1 0 29 79 1 0 30 80 1 0 30 81 1 0 31 82 1 0 31 83 1 0 32 84 1 0 34 85 1 0 34 86 1 0 34 87 1 0 35 88 1 0 35 89 1 0 36 90 1 0 36 91 1 0 37 92 1 0 39 93 1 0 39 94 1 0 39 95 1 0 40 96 1 0 40 97 1 0 40 98 1 0 M END

Standard InCHIKey	ATCICVFRSJQYDV-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C40H58/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15-17,19-22,25-31H,13-14,18,23-24,32H2,1-10H3
SMILES	CC(C)=CCCC(C)=CC=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)CCC=C(C)CCC=C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	538.45	Volume:	668.758 ? Van der Waals volume.
Dense:	0.805	LogP:	15.303 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	8.154 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-11.434 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	12.0
TPSA:	0.0 ? Topological Polar Surface Area.	H-Bond Acceptor:	0.0
H-Bond Donor:	0.0	Rings:	0.0
Heavy Atoms:	0.0

MedChem Properties

QED Drug-Likeness Score:	0.128	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.55	Fsp³:	0.4
MCE-18:	0.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	1.0	Fluc inhibitor:	0.667 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.0 ? 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:	0.671	Promiscuous compounds:	0.072

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.822	MDCK Permeability:	-4.737
Pgp-inhibitor:	0.999	Pgp-substrate:	0.587
PAMPA:	0.107 ? 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%):	0.011	30% Bioavailability (F30%):	0.032
50% Bioavailability (F50%):	0.924

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.995	MRP1:	0.999
Plasma Protein Binding (PPB):	96.949%	Volume Distribution (VD):	0.186
Fu:	2.996% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.324	BCRP inhibitor:	0.005
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.628	CYP1A2-substrate:	0.996
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.997	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.984	CYP2D6-substrate:	0.886
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.96	CYP2C8-inhibitor:	0.992
HLM stability:	0.995 ? 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):

9.636

Half-life (T1/2):

0.313

ADMET: Toxicity

hERG Blockers:	0.415	hERG Blockers (10um):	0.76
Human Hepatotoxicity (H-HT):	0.302	Drug-induced Liver Injury (DILI):	0.058
AMES Toxicity:	0.32	Rat Oral Acute Toxicity:	0.483
Maximum Recommended Daily Dose:	0.524	Skin Sensitization:	0.999
Carcinogencity:	0.569	Eye Corrosion:	0.34
Eye Irritation:	0.925	Respiratory Toxicity:	0.945
Drug-induced Neurotoxicity:	0.74	Ototoxicity:	0.237
Hematotoxicity:	0.189	Drug-induced Nephrotoxicity:	0.711
Genotoxicity:	0.014	RPMI-8226 Immunitoxicity:	0.135
A549 Cytotoxicity:	0.302	Hek293 Cytotoxicity:	0.17
BCF:	3.291 ? 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:	6.012 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.446 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	8.612 ? 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
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	DOI[10.1016/j.biotechadv.2015.06.003]
NPO13512	Opuntia ficus-indica	Species	Cactaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.indcrop.2014.08.046]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003Ã¢â‚¬â€œ2005	DOI[10.1016/j.jfca.2006.05.007]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jplph.2011.12.019]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0014-5793(03)00033-4]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ac991142i]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1034/j.1399-3054.2003.00030.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1046/j.1365-3040.2001.00686.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.274.1.397]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M302362200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M314195200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M411109200]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1093/jxb/erx356]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1104/pp.103.022368]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11005203]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11551769]
NPO17888	Myxococcus xanthus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12141877]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12637544]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12805618]
NPO17888	Myxococcus xanthus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14575429]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14745019]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	Himeji City, Japan	n.a.	PMID[15053555]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15280363]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15820655]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15834012]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[15844959]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1593278]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	PMID[1612412]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1684022]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17611796]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17764147]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18057039]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18232659]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18235971]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18318836]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	Northeastern Regional Plant Introduction Station at Geneva	1966, 1967, and 1968 crop seasons	PMID[18460139]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19521717]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21193570]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21194489]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21395888]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21608987]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21693706]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800258]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21939253]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22101040]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23370715]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23950498]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[24163311]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24285094]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[25457500]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25730866]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[27363486]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27432888]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2831703]
NPO17888	Myxococcus xanthus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31465225]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37980871]
NPO13512	Opuntia ficus-indica	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39339457]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[5447649]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[809439]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8278506]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO7826	Agrobacterium aurantiacum	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8970	Citrullus lanatus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO61328	Erwinia herbicola strain Eho10	Genus	Erwiniaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO64458	Erwinia herbicola strain Eho13	Genus	Erwiniaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO59146	Erwinia uredovora	Species	Erwiniaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO52278	Flavobacterium sp. Strain R1534	Genus	Flavobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO60770	Ipomoea batatas Lam.	Genus	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO61065	Neurospora crassa YLO	Genus	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9157	Rubrivivax gelatinosus	Species	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13512	Opuntia ficus-indica	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO54423	Anabaena sp. Strain PCC7120	Genus	Nostocaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17888	Myxococcus xanthus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO42791	Rhodobacter capsulatus	Species	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO50577	Sorangium compositum	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4316	Ananas sativus	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO59820	Rhodobaca bogoriensis	Genus	Paracoccaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO45422	Rhodobacter viridis JA737	Genus	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO61179	Rhodopseudomonas globiformis	Species	Acetobacteraceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8970	Citrullus lanatus	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8970	Citrullus lanatus	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8970	Citrullus lanatus	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13512	Opuntia ficus-indica	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13512	Opuntia ficus-indica	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[TCMID]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8970	Citrullus lanatus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17888	Myxococcus xanthus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9157	Rubrivivax gelatinosus	Species	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4316	Ananas sativus	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8970	Citrullus lanatus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7826	Agrobacterium aurantiacum	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13512	Opuntia ficus-indica	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC566125 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	42061
0.1-0.2	6964
0.2-0.3	685
0.3-0.4	125
0.4-0.5	17
0.5-0.6	4
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC99088
0.9231	High Similarity	NPC173592
0.7692	Intermediate Similarity	NPC305759
0.5556	Remote Similarity	NPC138935
0.5556	Remote Similarity	NPC123965
0.5556	Remote Similarity	NPC115959
0.5455	Remote Similarity	NPC604204

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC566125 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8886
0.1-0.2	234
0.2-0.3	18
0.3-0.4	10
0.4-0.5	1
0.5-0.6	1
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
0.5526	Remote Similarity	NPD4220	Phase 3

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