NPASS Compound

Natural Product: NPC129717

Natural Product ID	NPC129717
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	AQLHQIPWEIVGRR-IPGIDAFISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10699331
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0002010] Hybrid peptides

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 86 89 0 0 0 0 0 0 0 0999 V2000 -1.9090 5.0350 -0.1864 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0497 4.0609 -0.0932 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4857 3.8903 1.3292 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7553 2.7615 -0.7857 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5825 2.0292 -0.2634 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4553 0.7586 -1.0940 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6793 0.7199 -2.0435 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1729 -0.3165 -0.7810 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3497 -1.5938 -1.1896 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5334 -2.4293 -0.1362 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0866 -2.0731 -0.4063 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7616 -3.0371 -0.6513 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1551 -2.7265 -0.9323 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6907 -1.6576 -1.0706 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0269 -0.3845 -1.1770 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3059 -0.0595 -1.9281 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5342 -0.6090 -1.4033 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2716 0.1009 -0.4667 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4707 -0.4020 0.0430 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9434 -1.6155 -0.3774 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2255 -2.3290 -1.3017 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0291 -1.8108 -1.8000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7681 -3.8912 -1.8923 Cl 0 0 0 0 0 0 0 0 0 0 0 0 9.1441 -2.1837 0.0927 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8820 -1.4418 1.0431 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9891 0.6088 -0.0470 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8452 1.7958 -0.4070 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7323 3.0999 -0.0451 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7219 3.4295 1.0080 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6454 4.9186 1.2931 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4482 2.7755 0.8105 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0191 2.1225 1.8196 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3521 2.7543 -0.3387 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1057 0.2876 1.2799 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9763 -3.8879 -1.0553 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6725 -2.1615 -1.4437 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6121 -2.1537 -0.2562 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9327 -2.6933 -0.4245 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8880 -3.0199 0.6541 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0602 -2.2756 0.6880 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0354 -2.4685 1.6337 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8517 -3.4496 2.6055 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6838 -4.1748 2.5548 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7031 -3.9817 1.6042 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7629 -1.2825 -0.5331 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2509 4.8677 -1.0595 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3422 5.0484 0.7692 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3321 6.0531 -0.2859 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9219 4.5126 -0.6548 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6861 3.4302 1.9503 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6938 4.9184 1.7338 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4199 3.3127 1.3319 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7285 2.9608 -1.8752 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6492 2.1075 -0.6125 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7544 1.6636 0.7451 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7063 -1.7664 -2.1106 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7906 -2.0744 0.8680 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6744 -3.4853 -0.2611 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1468 -1.0404 -0.3514 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4391 -4.0502 -0.6502 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2238 0.1032 -1.8949 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1771 -0.4461 -2.9875 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3670 1.0498 -2.0474 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9632 1.0603 -0.0895 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0552 0.1619 0.7838 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5023 -2.3917 -2.5114 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2011 -0.4534 0.6214 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3337 -1.2366 1.9777 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8065 -2.0094 1.2521 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7302 3.6075 0.2146 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4325 3.7112 -0.9669 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1765 3.0032 1.9732 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3825 5.5232 0.4253 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9435 5.0248 2.1539 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6530 5.2289 1.6641 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5764 0.9147 1.9501 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9715 -3.7222 -1.1163 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1103 -1.7451 -2.3505 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5229 -3.2629 -1.6715 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2207 -2.0070 0.7642 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2067 -3.1308 -1.4227 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2378 -1.4918 -0.0654 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9409 -1.8657 1.6289 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6106 -3.6288 3.3726 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5369 -4.9419 3.3101 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7848 -4.5525 1.5662 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 21 23 1 0 20 24 1 0 24 25 1 0 15 26 1 0 26 27 2 3 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 31 32 2 0 31 33 1 0 26 34 1 0 13 35 1 0 9 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 38 45 1 0 33 5 1 0 45 37 1 0 22 17 1 0 44 39 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 0 3 50 1 0 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 5 55 1 1 9 56 1 6 10 57 1 0 10 58 1 0 11 59 1 0 12 60 1 0 15 61 1 6 16 62 1 0 16 63 1 0 18 64 1 0 19 65 1 0 22 66 1 0 25 67 1 0 25 68 1 0 25 69 1 0 28 70 1 0 28 71 1 0 29 72 1 1 30 73 1 0 30 74 1 0 30 75 1 0 34 76 1 0 35 77 1 0 36 78 1 0 36 79 1 0 37 80 1 1 38 81 1 6 40 82 1 0 41 83 1 0 42 84 1 0 43 85 1 0 44 86 1 0 M END

Standard InCHIKey	AQLHQIPWEIVGRR-IPGIDAFISA-N
Standard InCHI	InChI=1S/C34H41ClN2O8/c1-20(2)15-29-34(41)43-24(18-28-31(44-28)23-9-6-5-7-10-23)11-8-12-30(38)37-26(32(39)36-19-21(3)33(40)45-29)17-22-13-14-27(42-4)25(35)16-22/h5-10,12-14,16,20-21,24,26,28-29,31H,11,15,17-19H2,1-4H3,(H,36,39)(H,37,38)/b12-8+/t21-,24+,26-,28-,29+,31-/m1/s1
SMILES	CC(C)C[C@H]1C(=O)O[C@@H](C/C=C/C(=N[C@H](Cc2ccc(c(c2)Cl)OC)C(=NC[C@@H](C)C(=O)O1)O)O)C[C@@H]1[C@@H](c2ccccc2)O1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	640.26	Volume:	640.919 ? Van der Waals volume.
Dense:	0.999	LogP:	3.577 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.702 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.116 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	33.0
TPSA:	139.54 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.258	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.44	Fsp³:	0.471
MCE-18:	89.64 ? 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:	0.995	Fluc inhibitor:	0.165 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.778 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.005	Promiscuous compounds:	0.103

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.223	MDCK Permeability:	-4.703
Pgp-inhibitor:	0.98	Pgp-substrate:	0.891
PAMPA:	0.56 ? 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%):	0.449	30% Bioavailability (F30%):	0.955
50% Bioavailability (F50%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.922
Plasma Protein Binding (PPB):	95.982%	Volume Distribution (VD):	-0.05
Fu:	3.413% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.978	BCRP inhibitor:	0.017
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.008	CYP1A2-substrate:	0.006
CYP2C19-inhibitor:	0.957	CYP2C19-substrate:	0.554
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.007	CYP2D6-substrate:	0.99
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.767
HLM stability:	0.993 ? 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):

4.17

Half-life (T1/2):

1.257

ADMET: Toxicity

hERG Blockers:	0.045	hERG Blockers (10um):	0.005
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.326	Rat Oral Acute Toxicity:	0.423
Maximum Recommended Daily Dose:	0.996	Skin Sensitization:	1.0
Carcinogencity:	0.221	Eye Corrosion:	0.0
Eye Irritation:	0.149	Respiratory Toxicity:	0.975
Drug-induced Neurotoxicity:	0.995	Ototoxicity:	0.895
Hematotoxicity:	0.094	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.064
A549 Cytotoxicity:	0.061	Hek293 Cytotoxicity:	0.143
BCF:	1.009 ? 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:	3.791 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.274 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.744 ? 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
NPO18618	Neurolaena lobata	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	DOI[10.1021/jo00416a020]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473413]
NPO4541	Capnella lacertiliensis	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608844]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17243726]
NPO18618	Neurolaena lobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO18618	Neurolaena lobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24476550]
NPO23436	Cladrastis sikokiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1537	Vaccinium arctostaphylos	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8426	Tinospora rumphii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8305	Katsuwonus pelamis	Species	Scombridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4198	Ungernia vvedenskyi	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1969	Streptomyces pilosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12744	Ajuga nipponensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8623	Anneissia japonica	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4541	Capnella lacertiliensis	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7788	Rana catesbeiana	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8811	Cytisus prolifer	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28833	Eleutherococcus sieboldianus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10879	Lasius meridionalis	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19804	Lycopodium saururus	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9705	Meyerozyma guilliermondii	Species	Debaryomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19541	Smilax moranensis	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18618	Neurolaena lobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7240	Osteospermum oppositifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO834	Peperomia clusiifolia	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8305	Katsuwonus pelamis	Species	Scombridae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12744	Ajuga nipponensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7240	Osteospermum oppositifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1969	Streptomyces pilosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8426	Tinospora rumphii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8305	Katsuwonus pelamis	Species	Scombridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4541	Capnella lacertiliensis	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7788	Rana catesbeiana	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18618	Neurolaena lobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8623	Anneissia japonica	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5335	Nostoc sp	Species	Nostocaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28833	Eleutherococcus sieboldianus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1537	Vaccinium arctostaphylos	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10879	Lasius meridionalis	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4198	Ungernia vvedenskyi	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12744	Ajuga nipponensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23436	Cladrastis sikokiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8811	Cytisus prolifer	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19804	Lycopodium saururus	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO834	Peperomia clusiifolia	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9705	Meyerozyma guilliermondii	Species	Debaryomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19541	Smilax moranensis	Species	Smilacaceae	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 NPC129717 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	17042
0.1-0.2	31512
0.2-0.3	1285
0.3-0.4	4
0.4-0.5	1
0.5-0.6	3
0.6-0.7	4
0.7-0.8	1
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
0.7979	Intermediate Similarity	NPC271958
0.7979	Intermediate Similarity	NPC45112
0.7979	Intermediate Similarity	NPC263507
0.7979	Intermediate Similarity	NPC482624
0.7979	Intermediate Similarity	NPC482625
0.7849	Intermediate Similarity	NPC269383
0.7143	Intermediate Similarity	NPC482601
0.7143	Intermediate Similarity	NPC151030
0.6804	Remote Similarity	NPC207675
0.6569	Remote Similarity	NPC134413
0.6373	Remote Similarity	NPC49315
0.604	Remote Similarity	NPC132771
0.5849	Remote Similarity	NPC86678
0.5524	Remote Similarity	NPC212699
0.5179	Remote Similarity	NPC227778

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC129717 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2678
0.1-0.2	6158
0.2-0.3	309
0.3-0.4	3
0.4-0.5	0
0.5-0.6	0
0.6-0.7	1
0.7-0.8	1
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
0.7979	Intermediate Similarity	NPD7959	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD8014	Clinical (unspecified phase)

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