NPASS Compound

Natural Product: NPC85091

Natural Product ID	NPC85091
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HHUIWONHQASLSE-QKUYTOGTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11422735
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

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 102106 0 0 0 0 0 0 0 0999 V2000 5.2427 -2.6913 1.3760 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9131 -1.5067 0.7850 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6588 -2.0130 -0.4697 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0607 -0.3873 0.3205 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1947 0.2762 1.3964 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4838 1.4083 0.6598 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2882 1.3294 0.5044 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1225 2.5442 0.1535 N 0 0 0 0 0 0 0 0 0 0 0 0 5.4648 2.9540 0.3773 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8463 3.3726 -1.0532 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5955 4.1633 -1.4573 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4721 3.5341 -0.6473 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4063 3.0408 -1.5369 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2757 1.8485 -1.9501 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2043 1.4190 -2.8219 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1324 1.7382 -2.2156 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2656 2.2217 -1.0753 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3659 2.6124 -0.2829 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2255 3.6541 -0.9954 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 4.1037 -0.2157 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6271 3.4644 -0.3138 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7374 3.8705 0.3870 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6566 4.9624 1.2394 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4479 5.5904 1.3388 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3238 5.1902 0.6383 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1523 1.5577 0.3672 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0174 0.3274 0.0391 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8023 -0.6976 0.6924 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0215 -0.8967 -0.2051 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9417 -1.9345 0.3072 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9538 -1.6183 1.1885 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8280 -2.5700 1.6822 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6932 -3.8765 1.2878 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6804 -4.2159 0.4002 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8116 -3.2718 -0.0905 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5606 -4.8755 1.7654 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0358 -1.9372 0.8164 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1011 -2.5973 1.9341 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2067 -2.6075 -0.0654 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8126 -2.4207 -1.4017 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0722 -3.7929 -2.0473 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0239 -4.7541 -0.9084 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5529 -3.8634 0.2905 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9015 -3.8582 0.3042 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6110 -3.0263 0.8480 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -1.8684 1.5944 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5494 -1.3998 2.3465 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2852 -0.6202 1.8658 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7186 -1.9714 3.6100 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5944 -4.9272 -0.3827 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0726 1.8762 1.3670 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2358 1.4603 -3.0051 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4512 3.9845 -1.9656 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9780 -3.5554 1.2434 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3555 -3.0370 0.8216 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1190 -2.6401 2.4770 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6778 -1.1655 1.5333 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5450 -1.3992 -0.6237 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0105 -1.8565 -1.3820 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8230 -3.1013 -0.4127 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3411 -0.8603 -0.4421 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6249 0.3216 -0.2854 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8467 0.7936 2.1320 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1541 2.2351 0.8140 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4846 3.8768 1.0342 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9581 2.4955 -1.6920 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7462 3.9654 -1.0374 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7892 5.1989 -1.1292 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4204 4.1198 -2.5471 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0532 4.3477 -0.0066 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2813 1.9475 -3.7909 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2340 0.3345 -3.0327 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9121 3.2241 0.5816 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6048 4.5777 -1.1971 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5053 3.2883 -1.9884 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7076 2.6075 -0.9758 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6983 3.3552 0.2989 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5542 5.2479 1.7700 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3517 6.4445 1.9943 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3801 5.7224 0.7485 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1855 -0.4277 1.6844 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6877 -1.1053 -1.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5637 0.0532 -0.2470 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0913 -0.6002 1.5203 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6026 -2.3098 2.3630 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5636 -5.2617 0.0767 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0185 -3.5188 -0.7800 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7763 -5.6763 1.1902 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3933 -1.6881 -1.9875 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2655 -2.1434 -1.4963 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1084 -3.7177 -2.4879 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3294 -3.9927 -2.8526 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0109 -5.2027 -0.6804 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2888 -5.5483 -0.9961 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9437 -4.3509 1.1761 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5405 -2.0122 2.4074 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0097 -1.0507 0.9088 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5284 -1.7166 4.2003 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6081 -4.9029 -0.4457 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9194 1.3837 1.5198 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0946 1.0670 -2.6311 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9947 3.9281 -2.8627 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 1 0 12 13 1 0 13 14 2 3 14 15 1 0 15 16 1 0 16 17 2 3 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 18 26 1 0 26 27 2 3 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 33 36 1 0 28 37 1 0 37 38 2 0 37 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 2 3 45 46 1 0 46 47 1 0 47 48 2 3 47 49 1 0 44 50 1 0 26 51 1 0 16 52 1 0 13 53 1 0 48 5 1 0 12 8 1 0 25 20 1 0 35 30 1 0 43 39 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 0 3 58 1 0 3 59 1 0 3 60 1 0 4 61 1 0 4 62 1 0 5 63 1 1 9 64 1 0 9 65 1 0 10 66 1 0 10 67 1 0 11 68 1 0 11 69 1 0 12 70 1 1 15 71 1 0 15 72 1 0 18 73 1 1 19 74 1 0 19 75 1 0 21 76 1 0 22 77 1 0 23 78 1 0 24 79 1 0 25 80 1 0 28 81 1 1 29 82 1 0 29 83 1 0 31 84 1 0 32 85 1 0 34 86 1 0 35 87 1 0 36 88 1 0 40 89 1 0 40 90 1 0 41 91 1 0 41 92 1 0 42 93 1 0 42 94 1 0 43 95 1 1 46 96 1 0 46 97 1 0 49 98 1 0 50 99 1 0 51100 1 0 52101 1 0 53102 1 0 M END

Standard InCHIKey	HHUIWONHQASLSE-QKUYTOGTSA-N
Standard InCHI	InChI=1S/C38H49N7O8/c1-23(2)18-28-37(52)44-16-6-10-30(44)35(50)39-21-32(47)41-27(19-24-8-4-3-5-9-24)34(49)43-29(20-25-12-14-26(46)15-13-25)38(53)45-17-7-11-31(45)36(51)40-22-33(48)42-28/h3-5,8-9,12-15,23,27-31,46H,6-7,10-11,16-22H2,1-2H3,(H,39,50)(H,40,51)(H,41,47)(H,42,48)(H,43,49)/t27-,28-,29-,30-,31-/m0/s1
SMILES	CC(C)C[C@H]1C(=O)N2CCC[C@H]2C(=NCC(=N[C@@H](Cc2ccccc2)C(=N[C@@H](Cc2ccc(cc2)O)C(=O)N2CCC[C@H]2C(=NCC(=N1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	731.36	Volume:	736.047 ? Van der Waals volume.
Dense:	0.994	LogP:	0.526 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.296 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.293 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	43.0
TPSA:	223.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.253	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.703	Fsp³:	0.5
MCE-18:	114.053 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.415	Fluc inhibitor:	0.163 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.742 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.007

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.994	MDCK Permeability:	-5.064
Pgp-inhibitor:	0.226	Pgp-substrate:	0.999
PAMPA:	0.494 ? 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):	0.461
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.941
Plasma Protein Binding (PPB):	45.461%	Volume Distribution (VD):	-0.194
Fu:	53.752% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.991
OATP1B3 inhibitor:	0.732	BCRP inhibitor:	0.046
BSEP inhibitor:	0.856

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.133	CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.991	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.99 ? 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):

0.416

Half-life (T1/2):

1.979

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.009	Rat Oral Acute Toxicity:	0.923
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.078	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.998
Drug-induced Neurotoxicity:	0.915	Ototoxicity:	0.996
Hematotoxicity:	0.253	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.005
BCF:	0.423 ? 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:	3.343 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.944 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.018 ? 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
NPO2253	Illicium jiadifengpi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975494]
NPO2558	Ceratodictyon spongiosum	Species	Lomentariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19670881]
NPO7761	Laurencia majuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8691206]
NPO2558	Ceratodictyon spongiosum	Species	Lomentariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3409	Goniothalamus leiocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1093	Plumeria obtusa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5796	Haplopappus foliosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1536	Lindera triloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2253	Illicium jiadifengpi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7607	Ophiorrhiza pumila	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7761	Laurencia majuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7450	Sida acuta	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3409	Goniothalamus leiocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7761	Laurencia majuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1536	Lindera triloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7450	Sida acuta	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3409	Goniothalamus leiocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2182	Athyrium filix-femina	Species	Athyriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7607	Ophiorrhiza pumila	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2253	Illicium jiadifengpi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1093	Plumeria obtusa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7450	Sida acuta	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7761	Laurencia majuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1536	Lindera triloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7450	Sida acuta	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3409	Goniothalamus leiocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8060	Lethariella cashmeriana	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7761	Laurencia majuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2182	Athyrium filix-femina	Species	Athyriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO274	Dendrobates viridis	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7607	Ophiorrhiza pumila	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6838	Senecio grisebachii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3114	Stylocheilus striatus	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2956	Echinometra oblonga	Species	Echinometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1693	Gnomonia fragariae	Species	Sydowiellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4276	Cupressus lindleyi	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11725	Cetonia aurata	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7450	Sida acuta	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3409	Goniothalamus leiocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5796	Haplopappus foliosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5262	Sargassum natans	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1536	Lindera triloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1093	Plumeria obtusa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2253	Illicium jiadifengpi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1878	Kunzea baxteri	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4805	Balanophora papuana	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2558	Ceratodictyon spongiosum	Species	Lomentariaceae	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 NPC85091 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	14804
0.1-0.2	32210
0.2-0.3	2346
0.3-0.4	345
0.4-0.5	111
0.5-0.6	26
0.6-0.7	13
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC141957
0.7375	Intermediate Similarity	NPC56685
0.6883	Remote Similarity	NPC486664
0.6824	Remote Similarity	NPC241794
0.6786	Remote Similarity	NPC136797
0.6543	Remote Similarity	NPC489829
0.65	Remote Similarity	NPC255447
0.6437	Remote Similarity	NPC262166
0.6341	Remote Similarity	NPC202521
0.6304	Remote Similarity	NPC275110
0.625	Remote Similarity	NPC224315
0.622	Remote Similarity	NPC202198
0.6143	Remote Similarity	NPC242159
0.6125	Remote Similarity	NPC242482
0.6118	Remote Similarity	NPC6975
0.5955	Remote Similarity	NPC101679
0.5854	Remote Similarity	NPC489593
0.5833	Remote Similarity	NPC489557
0.5778	Remote Similarity	NPC489825
0.5778	Remote Similarity	NPC489826
0.5765	Remote Similarity	NPC485094
0.5729	Remote Similarity	NPC328649
0.5684	Remote Similarity	NPC489828
0.5571	Remote Similarity	NPC285926
0.5571	Remote Similarity	NPC14672
0.5556	Remote Similarity	NPC130309
0.5532	Remote Similarity	NPC302597
0.5435	Remote Similarity	NPC261934
0.5309	Remote Similarity	NPC200589
0.5281	Remote Similarity	NPC479072
0.5269	Remote Similarity	NPC300315
0.5229	Remote Similarity	NPC484665
0.5222	Remote Similarity	NPC489556
0.5217	Remote Similarity	NPC479074
0.5146	Remote Similarity	NPC296968
0.5146	Remote Similarity	NPC489823
0.5114	Remote Similarity	NPC16188
0.5111	Remote Similarity	NPC489592
0.5109	Remote Similarity	NPC5194
0.5052	Remote Similarity	NPC487308
0.5052	Remote Similarity	NPC487309

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC85091 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2349
0.1-0.2	6243
0.2-0.3	498
0.3-0.4	51
0.4-0.5	8
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
0.5618	Remote Similarity	NPD7118	Phase 2

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