NPASS Compound

Natural Product: NPC173592

Natural Product ID	NPC173592
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(6Z,8E,10Z,12E,14Z,16E,18Z,20E,22Z,24E,26Z)-2,6,10,14,19,23,27,31-Octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-Tridecaene
IUPAC Name	(6Z,8E,10Z,12E,14Z,16E,18Z,20E,22Z,24E,26Z)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1984187
PubChem CID	54603520
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001554] Tetraterpenoids [CHEMONTID:0001277] Carotenoids [CHEMONTID:0001411] Carotenes

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 96 95 0 0 0 0 0 0 0 0999 V2000 3.9478 0.0213 3.9697 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8343 0.1118 2.9629 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5893 0.0716 3.3740 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4728 0.1397 2.5500 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5454 0.1946 1.8819 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8928 0.2927 0.5024 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1643 0.2857 0.1366 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2375 0.1758 1.0796 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5307 0.1639 0.6897 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5967 0.0477 1.6577 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8554 0.0279 1.2814 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2606 0.1272 -0.1133 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5720 0.0584 -0.4313 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9287 0.1671 -1.8309 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1730 0.0729 -2.2428 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2590 -0.1593 -1.2800 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3164 0.9251 -1.2368 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.3045 0.4300 -0.2031 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.5658 0.1776 -0.5273 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.4988 -0.3148 0.5374 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.0990 0.3580 -1.8947 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4910 0.2116 -3.7240 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9124 -0.0923 2.3330 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4139 0.4024 -1.3151 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1373 0.3071 1.5520 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4050 0.3307 1.1304 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7180 0.5270 -0.2537 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9868 0.5369 -0.6744 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0875 0.3461 0.2509 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3620 0.3470 -0.0906 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3765 0.1421 0.9268 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6639 0.1182 0.7123 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2395 0.3023 -0.6077 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0119 -0.8409 -1.1804 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1405 -1.3624 -0.4201 C 0 0 0 0 0 0 0 0 0 0 0 0 14.4226 -1.2711 -0.7915 C 0 0 0 0 0 0 0 0 0 0 0 0 14.8410 -0.6061 -2.0545 C 0 0 0 0 0 0 0 0 0 0 0 0 15.4826 -1.8606 0.0762 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5772 -0.0834 1.8945 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2742 0.7527 -2.1213 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5195 -0.9229 3.7582 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6056 0.8842 3.8880 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5009 -0.0768 4.9738 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5121 0.0109 4.5037 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2060 -0.8057 3.3975 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4259 0.3956 2.6303 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0928 0.3658 -0.2618 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1222 0.0912 2.1367 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7291 0.2349 -0.3442 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3708 -0.0242 2.7366 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5379 0.2561 -0.9152 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2288 -0.0626 0.3840 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1368 0.3379 -2.5879 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8275 -1.0630 -1.7091 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9742 -0.4926 -0.2860 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7765 1.1184 -2.2018 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8653 1.8599 -0.8575 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9189 0.2975 0.7936 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.9920 -1.1715 1.0784 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.7212 0.5411 1.1963 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.4229 -0.7239 0.0780 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.1527 0.0252 -1.9345 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.5159 -0.2774 -2.6240 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.0670 1.4024 -2.2559 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4914 1.3290 -3.8719 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6908 -0.2142 -4.3461 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5006 -0.1268 -3.9469 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5219 0.8209 2.3923 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4561 -0.3918 3.3050 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5575 -0.9608 2.0357 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6346 -0.5709 -1.7830 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5500 0.8764 -1.8495 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3136 1.0737 -1.4426 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3506 0.4453 0.8454 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1218 0.1871 1.9244 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9779 0.6786 -1.0292 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8950 0.1839 1.3233 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6291 0.4997 -1.1046 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0771 -0.0075 1.9850 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9644 1.1763 -0.5803 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5193 0.6132 -1.4061 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4012 -0.4701 -2.1771 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3424 -1.6932 -1.4740 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9430 -1.8948 0.5304 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7403 0.5003 -1.8894 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8952 -0.8967 -2.2570 H 0 0 0 0 0 0 0 0 0 0 0 0 14.2343 -0.8767 -2.9347 H 0 0 0 0 0 0 0 0 0 0 0 0 16.3751 -2.0928 -0.5653 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8170 -1.1997 0.8872 H 0 0 0 0 0 0 0 0 0 0 0 0 15.1722 -2.8824 0.4544 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6115 0.1710 1.6270 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5361 -1.1302 2.2322 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1724 0.6106 2.6819 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3375 1.8384 -2.3294 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3948 0.3509 -2.7166 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2015 0.2705 -2.4672 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 3 19 20 1 0 19 21 1 0 15 22 1 0 11 23 1 0 7 24 1 0 2 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 2 3 36 37 1 0 36 38 1 0 32 39 1 0 28 40 1 0 1 41 1 0 1 42 1 0 1 43 1 0 3 44 1 0 4 45 1 0 5 46 1 0 6 47 1 0 8 48 1 0 9 49 1 0 10 50 1 0 12 51 1 0 13 52 1 0 14 53 1 0 16 54 1 0 16 55 1 0 17 56 1 0 17 57 1 0 18 58 1 0 20 59 1 0 20 60 1 0 20 61 1 0 21 62 1 0 21 63 1 0 21 64 1 0 22 65 1 0 22 66 1 0 22 67 1 0 23 68 1 0 23 69 1 0 23 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 30 78 1 0 31 79 1 0 33 80 1 0 33 81 1 0 34 82 1 0 34 83 1 0 35 84 1 0 37 85 1 0 37 86 1 0 37 87 1 0 38 88 1 0 38 89 1 0 38 90 1 0 39 91 1 0 39 92 1 0 39 93 1 0 40 94 1 0 40 95 1 0 40 96 1 0 M END

Standard InCHIKey	OAIJSZIZWZSQBC-LWRKPGOESA-N
Standard InCHI	InChI=1S/C40H56/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/h11-12,15-22,25-32H,13-14,23-24H2,1-10H3/b12-11+,25-15+,26-16+,31-17+,32-18+,35-21-,36-22-,37-27-,38-28-,39-29-,40-30-
SMILES	C/C(=C/C=C/C=C(C=CC=C(/C=C/C=C(CCC=C(C)C)/C)C)/C)/C=C/C=C(C=CC=C(/CCC=C(C)C)C)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	536.44	Volume:	666.122 ? Van der Waals volume.
Dense:	0.805	LogP:	11.314 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	6.521 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-10.715 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	13.0
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:	0.136	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.566	Fsp³:	0.35
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:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.67	Promiscuous compounds:	0.08

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.548	MDCK Permeability:	-4.687
Pgp-inhibitor:	0.997	Pgp-substrate:	0.982
PAMPA:	0.012 ? 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%):	0.081	30% Bioavailability (F30%):	0.685
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	96.996%	Volume Distribution (VD):	0.174
Fu:	3.423% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.581	BCRP inhibitor:	0.002
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.108	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.806	CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.921	CYP2C9-substrate:	0.747
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.969 ? 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):

9.818

Half-life (T1/2):

0.462

ADMET: Toxicity

hERG Blockers:	0.516	hERG Blockers (10um):	0.815
Human Hepatotoxicity (H-HT):	0.368	Drug-induced Liver Injury (DILI):	0.051
AMES Toxicity:	0.238	Rat Oral Acute Toxicity:	0.818
Maximum Recommended Daily Dose:	0.967	Skin Sensitization:	1.0
Carcinogencity:	0.862	Eye Corrosion:	0.0
Eye Irritation:	0.061	Respiratory Toxicity:	0.774
Drug-induced Neurotoxicity:	0.845	Ototoxicity:	0.403
Hematotoxicity:	0.228	Drug-induced Nephrotoxicity:	0.972
Genotoxicity:	0.014	RPMI-8226 Immunitoxicity:	0.179
A549 Cytotoxicity:	0.301	Hek293 Cytotoxicity:	0.599
BCF:	3.281 ? 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:	5.903 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.829 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	8.641 ? 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
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s11306-014-0728-9]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	DOI[10.1016/0045-6535(91)90110-Y]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.abb.2017.09.009]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2004.07.004]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO163	Daucus carota	Species	Apiaceae	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.	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]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0885-5765(05)80069-4]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1038/sdata.2014.29]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1093/jxb/erx356]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11171227]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141864]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12576668]
NPO683	Rosa canina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880322]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	Himeji City, Japan	n.a.	PMID[15053555]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[17190444]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17685651]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17764147]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	Northeastern Regional Plant Introduction Station at Geneva	1966, 1967, and 1968 crop seasons	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]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[18637688]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19245240]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	calyx	n.a.	PMID[21561086]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21800857]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327299]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	fruit	n.a.	PMID[24086493]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24836069]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	seed	n.a.	PMID[25891114]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2831703]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2831703]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28621938]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Vines	n.a.	n.a.	PMID[32357011]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37324556]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37980871]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38440938]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987503]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7273	Brassica rutabaga	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1141	Citrus sp.	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO683	Rosa canina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31235	Citrus sp	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO683	Rosa canina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7273	Brassica rutabaga	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	Database[MetaboLights]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1141	Citrus sp.	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO683	Rosa canina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7273	Brassica rutabaga	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO683	Rosa canina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO683	Rosa canina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7273	Brassica rutabaga	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28919	Calendula officinalis	Species	Asteraceae	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
GI50	54

Activity Type	# Activity
Cell line	54

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
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT457	Cell line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT306	Cell line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set

In vivo activity

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

Experimental ADME

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

Experimental Toxicity

Quantitative toxicity

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

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 NPC173592 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	41962
0.1-0.2	7192
0.2-0.3	617
0.3-0.4	71
0.4-0.5	12
0.5-0.6	1
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC99088
0.6923	Remote Similarity	NPC305759
0.5714	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 NPC173592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8865
0.1-0.2	255
0.2-0.3	20
0.3-0.4	8
0.4-0.5	1
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