NPASS Compound

Natural Product: NPC92598

Natural Product ID	NPC92598
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CGSGRJNIABXQJQ-CAAOHEDASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6440205
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003494] Rhamnofolane and daphnane diterpenoids

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 91 97 0 0 0 0 0 0 0 0999 V2000 10.8149 -0.4197 1.8918 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4303 0.0626 1.4688 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5524 -1.1603 1.2380 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1670 -0.7929 0.8175 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4310 0.0527 1.8258 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0711 0.3183 1.2362 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9699 -0.0671 1.8491 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6259 0.1571 1.3357 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5487 -0.2461 1.9836 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1787 -0.0055 1.4390 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7820 -0.0294 2.4337 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8786 0.4739 1.7014 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3631 -0.7691 0.9266 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7370 -1.7936 1.9035 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2678 -3.0331 1.6069 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2293 -3.7318 2.5858 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3279 -2.9058 3.6985 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1245 -3.7542 0.3490 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6581 -2.9947 -0.8321 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3101 -2.4171 -0.5712 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4528 -2.7414 -1.7083 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0652 -3.6109 -2.4867 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5515 -4.2189 -3.7658 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3764 -3.9468 -1.9485 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1654 -4.8466 -2.3065 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2978 -1.0164 -0.0857 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5520 0.0286 -1.1670 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6701 -0.0519 -2.3573 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4462 1.4305 -0.6049 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2465 1.5021 0.8540 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6384 2.8615 1.3470 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6822 3.7132 1.6913 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0680 3.2643 1.4530 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1493 1.3484 1.0781 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5503 2.2386 -0.9656 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4405 3.3824 -1.7425 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2821 3.6838 -2.1278 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5827 4.2095 -2.1089 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8589 3.9336 -1.7206 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9084 4.7733 -2.1098 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6903 5.8867 -2.8846 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4068 6.1631 -3.2745 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3736 5.3290 -2.8864 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0082 -0.7864 0.3692 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6264 -2.1179 -1.2286 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3681 -4.3394 0.0181 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9503 -2.8674 2.2815 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5801 0.3161 1.5845 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9959 -1.3741 1.3490 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7941 -0.5773 2.9809 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5640 0.6413 0.5404 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9805 0.6822 2.2602 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5936 -1.8135 2.1198 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0233 -1.7177 0.4039 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2519 -0.1830 -0.1195 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6234 -1.7255 0.5900 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3050 -0.4904 2.7738 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9938 1.0000 1.9468 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9973 0.8304 0.3004 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0685 -0.5812 2.7906 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4584 0.6699 0.3911 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 -0.7572 2.9258 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6705 0.8485 2.3750 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3121 -0.4060 0.4279 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1748 -1.3136 2.8500 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2188 -3.8259 2.1144 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8585 -4.7468 2.8335 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1828 -2.3993 3.6506 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4239 -4.6247 0.4990 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8402 -3.0254 0.2686 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5263 -2.3611 -1.9156 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0595 -3.4137 -4.2527 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1146 -5.0686 -3.5746 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3952 -4.4468 -4.4312 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6120 -0.0510 -1.5499 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4121 -0.0005 -2.1297 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8422 0.9266 -2.9147 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9497 -0.8010 -3.1228 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5499 1.9446 -1.0763 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3800 3.4446 1.6232 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9786 4.6921 2.0451 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3214 3.4662 2.5186 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7440 2.5387 0.9918 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1957 4.2340 0.9053 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0621 3.0652 -1.1107 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9067 4.5311 -1.7880 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4887 6.5571 -3.2019 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2402 7.0421 -3.8859 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3674 5.5775 -3.2132 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7469 -2.1463 -2.1943 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3630 -5.3070 0.0867 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 16 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 22 24 1 0 24 25 2 0 20 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 30 31 1 1 31 32 2 0 31 33 1 0 30 34 1 0 29 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 26 44 1 1 19 45 1 6 18 46 1 0 15 47 1 0 34 10 1 0 43 38 1 0 44 10 1 0 30 12 1 0 26 13 1 0 47 14 1 0 24 19 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 0 2 52 1 0 3 53 1 0 3 54 1 0 4 55 1 0 4 56 1 0 5 57 1 0 5 58 1 0 6 59 1 0 7 60 1 0 8 61 1 0 9 62 1 0 12 63 1 1 13 64 1 6 14 65 1 1 16 66 1 0 16 67 1 0 17 68 1 0 18 69 1 1 20 70 1 1 21 71 1 0 23 72 1 0 23 73 1 0 23 74 1 0 27 75 1 6 28 76 1 0 28 77 1 0 28 78 1 0 29 79 1 6 32 80 1 0 32 81 1 0 33 82 1 0 33 83 1 0 33 84 1 0 39 85 1 0 40 86 1 0 41 87 1 0 42 88 1 0 43 89 1 0 45 90 1 0 46 91 1 0 M END

Standard InCHIKey	CGSGRJNIABXQJQ-CAAOHEDASA-N
Standard InCHI	InChI=1S/C37H44O10/c1-6-7-8-9-10-11-15-18-34-45-30-26-29-33(20-38,44-29)32(41)35(42)25(19-22(4)27(35)39)37(26,47-34)23(5)28(36(30,46-34)21(2)3)43-31(40)24-16-13-12-14-17-24/h10-19,23,25-26,28-30,32,38,41-42H,2,6-9,20H2,1,3-5H3/b11-10+,18-15+/t23-,25-,26+,28-,29+,30-,32-,33+,34?,35-,36+,37+/m1/s1
SMILES	CCCCC/C=C/C=C/C12O[C@@H]3[C@@H]4[C@H]5[C@@](CO)([C@H]([C@]6([C@@H](C=C(C)C6=O)[C@]4([C@H](C)[C@H]([C@]3(C(=C)C)O1)OC(=O)c1ccccc1)O2)O)O)O5

Calculated Properties

Physi-Chem Properties

Molecular Weight:	648.29	Volume:	652.787 ? Van der Waals volume.
Dense:	0.993	LogP:	4.116 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.869 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.236 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	35.0
TPSA:	144.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	3.0	Rings:	7.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.113	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.696	Fsp³:	0.568
MCE-18:	163.862 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.627	Fluc inhibitor:	0.246 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.037 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.106	Promiscuous compounds:	0.189

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.286	MDCK Permeability:	-4.964
Pgp-inhibitor:	0.141	Pgp-substrate:	0.012
PAMPA:	0.038 ? 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%):	0.269	30% Bioavailability (F30%):	0.987
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087	MRP1:	0.988
Plasma Protein Binding (PPB):	95.953%	Volume Distribution (VD):	-0.124
Fu:	3.18% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.13
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.831
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.783
CYP2C9-inhibitor:	0.014	CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.971
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.442 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.417

Half-life (T1/2):

0.874

ADMET: Toxicity

hERG Blockers:	0.099	hERG Blockers (10um):	0.41
Human Hepatotoxicity (H-HT):	0.381	Drug-induced Liver Injury (DILI):	0.283
AMES Toxicity:	0.899	Rat Oral Acute Toxicity:	0.386
Maximum Recommended Daily Dose:	0.251	Skin Sensitization:	1.0
Carcinogencity:	0.401	Eye Corrosion:	0.001
Eye Irritation:	0.241	Respiratory Toxicity:	0.401
Drug-induced Neurotoxicity:	0.406	Ototoxicity:	0.831
Hematotoxicity:	0.617	Drug-induced Nephrotoxicity:	0.482
Genotoxicity:	0.037	RPMI-8226 Immunitoxicity:	0.174
A549 Cytotoxicity:	0.751	Hek293 Cytotoxicity:	0.808
BCF:	1.543 ? 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:	4.557 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.913 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.447 ? 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
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	flower	n.a.	PMID[21916433]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[23558238]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228307]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31150241]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31860304]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223193]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32997496]
NPO6789	Gnidia latifolia	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5087	Daphne oleoides	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6789	Gnidia latifolia	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5087	Daphne oleoides	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8844	Stillingia sylvatica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8844	Stillingia sylvatica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5087	Daphne oleoides	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6789	Gnidia latifolia	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8844	Stillingia sylvatica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6789	Gnidia latifolia	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5087	Daphne oleoides	Species	Thymelaeaceae	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
FC	1
Activity	2

Activity Type	# Activity
Cell line	1
Single protein	1
Organism	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT17120	Single protein	Nuclear receptor subfamily 4 group A member 2	Mus musculus	FC	=	3.5	n.a.	PMID[27228307]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell line	3T3-L1	Mus musculus	Activity	>	50.0	%	PMID[37014798]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	40.28	%	PMID[27228307]

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 NPC92598 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	8866
0.1-0.2	39023
0.2-0.3	1808
0.3-0.4	77
0.4-0.5	31
0.5-0.6	10
0.6-0.7	12
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC43304
1.0	High Similarity	NPC481753
1.0	High Similarity	NPC477188
1.0	High Similarity	NPC477190
0.9286	High Similarity	NPC164150
0.9286	High Similarity	NPC481754
0.7791	Intermediate Similarity	NPC182266
0.7791	Intermediate Similarity	NPC475154
0.7791	Intermediate Similarity	NPC485700
0.7766	Intermediate Similarity	NPC101786
0.7674	Intermediate Similarity	NPC223356
0.7674	Intermediate Similarity	NPC298697
0.7674	Intermediate Similarity	NPC475500
0.7674	Intermediate Similarity	NPC100017
0.7674	Intermediate Similarity	NPC481742
0.7586	Intermediate Similarity	NPC75831
0.7586	Intermediate Similarity	NPC471137
0.7528	Intermediate Similarity	NPC605479
0.7527	Intermediate Similarity	NPC481745
0.75	Intermediate Similarity	NPC471136
0.75	Intermediate Similarity	NPC116727
0.75	Intermediate Similarity	NPC39509
0.7416	Intermediate Similarity	NPC481744
0.7416	Intermediate Similarity	NPC481743
0.7188	Intermediate Similarity	NPC130886
0.7188	Intermediate Similarity	NPC486153
0.7159	Intermediate Similarity	NPC180902
0.7071	Intermediate Similarity	NPC481773
0.7045	Intermediate Similarity	NPC324104
0.7045	Intermediate Similarity	NPC473548
0.6698	Remote Similarity	NPC69240
0.6667	Remote Similarity	NPC474508
0.6667	Remote Similarity	NPC473485
0.6667	Remote Similarity	NPC171411
0.6667	Remote Similarity	NPC485701
0.6593	Remote Similarity	NPC485693
0.6556	Remote Similarity	NPC251564
0.6556	Remote Similarity	NPC477189
0.6535	Remote Similarity	NPC481774
0.6484	Remote Similarity	NPC475314
0.6484	Remote Similarity	NPC102997
0.6204	Remote Similarity	NPC191992
0.5978	Remote Similarity	NPC162495
0.5938	Remote Similarity	NPC61891
0.5914	Remote Similarity	NPC475606
0.54	Remote Similarity	NPC254588
0.5377	Remote Similarity	NPC68282
0.5377	Remote Similarity	NPC486154
0.5283	Remote Similarity	NPC251139
0.5283	Remote Similarity	NPC156682
0.5283	Remote Similarity	NPC49297
0.51	Remote Similarity	NPC322420

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC92598 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3406
0.1-0.2	5666
0.2-0.3	78
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data