NPASS Compound

Natural Product: NPC222898

Natural Product ID	NPC222898
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LEMIZUSBKJGJDW-OQYXBDBKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	72714832
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 84 88 0 0 0 0 0 0 0 0999 V2000 -3.7412 1.8748 1.6907 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5202 1.3484 0.5029 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6682 2.3561 0.3268 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1785 0.0210 0.7785 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0987 -0.9241 -0.3659 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6642 -1.1697 -0.7961 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0154 -2.0319 0.2326 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5146 -2.1045 0.1674 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8451 -0.7719 0.0849 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7041 -0.2501 1.5031 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5556 0.1807 -0.8099 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8995 1.1892 -1.3827 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5385 1.4753 -1.2119 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1786 0.4269 -0.3960 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5558 -0.9158 -0.5568 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2672 -1.2648 -2.0088 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3025 -2.0548 0.0350 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7240 -1.8733 0.3654 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1375 -0.4491 0.6336 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5525 -0.3592 1.0496 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4585 -1.3967 0.4150 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6122 -0.7065 2.5522 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1283 1.0329 0.9504 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0072 2.0517 0.8934 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2823 1.7890 -0.4287 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7073 0.4049 -0.5100 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1235 -0.1361 -1.8611 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2895 1.9820 -1.4086 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1813 2.0445 1.9797 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9274 1.2209 -0.1563 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0185 0.1007 -1.1378 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7121 1.3733 -0.7435 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5027 1.8920 -1.7989 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7986 -2.0430 -2.0222 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3529 -1.5767 -3.0948 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3718 -3.2841 -1.9988 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4340 2.3797 2.3813 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0477 2.6682 1.3046 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1801 1.0697 2.2072 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2739 3.3694 0.5064 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1102 2.2181 -0.6794 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4312 2.1757 1.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2765 0.1306 1.0273 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7345 -0.3864 1.7094 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6834 -0.5190 -1.2137 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5465 -1.8868 -0.0624 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3895 -3.0670 0.0867 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3233 -1.7802 1.2901 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2244 -2.5922 1.1475 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1925 -2.8053 -0.6251 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2126 -0.6239 2.0021 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8261 0.8492 1.5678 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5475 -0.6801 2.1206 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4359 1.8876 -2.0431 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5630 2.4600 -0.6524 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0504 1.7008 -2.1687 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0095 0.7140 0.6884 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4387 -0.4145 -2.6949 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7857 -1.5675 -2.1830 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8485 -2.1775 -2.3364 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2124 -2.9876 -0.5941 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7717 -2.3397 0.9882 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4290 -2.3141 -0.3776 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9905 -2.4249 1.3212 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5105 -0.1402 1.5256 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5073 -1.0020 0.5621 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3186 -1.5323 -0.6489 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4478 -2.3535 0.9958 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4706 -1.7748 2.7181 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5452 -0.2914 2.9857 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7743 -0.1057 3.0120 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7442 1.3080 1.8425 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4454 3.0695 0.8087 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5825 2.6044 -0.5723 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9972 -1.1938 -2.0121 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6372 0.5164 -2.6359 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2195 0.1086 -2.0002 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3032 2.8926 -1.7487 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8413 2.9326 2.2432 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8687 0.9962 -0.0300 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0113 0.1530 -2.2794 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9137 2.1473 -0.6026 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4999 2.8733 -1.7709 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6840 -3.7166 -2.8659 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 1 0 7 8 1 0 8 9 1 0 9 10 1 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 25 28 1 0 24 29 1 0 23 30 1 0 11 31 1 0 31 32 1 0 32 33 1 0 6 34 1 6 34 35 2 0 34 36 1 0 32 2 1 0 31 6 1 0 15 9 1 0 26 19 1 0 26 14 1 0 1 37 1 0 1 38 1 0 1 39 1 0 3 40 1 0 3 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 5 45 1 0 5 46 1 0 7 47 1 0 7 48 1 0 8 49 1 0 8 50 1 0 10 51 1 0 10 52 1 0 10 53 1 0 12 54 1 0 13 55 1 0 13 56 1 0 14 57 1 1 16 58 1 0 16 59 1 0 16 60 1 0 17 61 1 0 17 62 1 0 18 63 1 0 18 64 1 0 19 65 1 1 21 66 1 0 21 67 1 0 21 68 1 0 22 69 1 0 22 70 1 0 22 71 1 0 23 72 1 1 24 73 1 6 25 74 1 6 27 75 1 0 27 76 1 0 27 77 1 0 28 78 1 0 29 79 1 0 30 80 1 0 31 81 1 6 32 82 1 1 33 83 1 0 36 84 1 0 M END

Standard InCHIKey	LEMIZUSBKJGJDW-OQYXBDBKSA-N
Standard InCHI	InChI=1S/C30H48O6/c1-25(2)12-14-30(24(35)36)15-13-27(5)16(19(30)21(25)32)8-9-18-28(27,6)11-10-17-26(3,4)22(33)20(31)23(34)29(17,18)7/h8,17-23,31-34H,9-15H2,1-7H3,(H,35,36)/t17-,18-,19+,20-,21+,22-,23+,27+,28+,29-,30-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@H]4[C@@]3(C)CC[C@H]3C(C)(C)[C@H]([C@@H]([C@H]([C@]43C)O)O)O)[C@@H]2[C@H]1O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	504.35	Volume:	532.122 ? Van der Waals volume.
Dense:	0.948	LogP:	2.686 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.68 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.481 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	118.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.343	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.172	Fsp³:	0.9
MCE-18:	113.474 ? 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:	0.797	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.229 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.283	Promiscuous compounds:	0.048

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.578	MDCK Permeability:	-5.136
Pgp-inhibitor:	0.001	Pgp-substrate:	0.009
PAMPA:	1.0 ? 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):	0.003
20% Bioavailability (F20%):	0.176	30% Bioavailability (F30%):	0.119
50% Bioavailability (F50%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.282	MRP1:	0.829
Plasma Protein Binding (PPB):	81.24%	Volume Distribution (VD):	-0.377
Fu:	16.58% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.937	BCRP inhibitor:	0.012
BSEP inhibitor:	0.839

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.006	CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.148 ? 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):

2.818

Half-life (T1/2):

1.542

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.041
Human Hepatotoxicity (H-HT):	0.526	Drug-induced Liver Injury (DILI):	0.49
AMES Toxicity:	0.241	Rat Oral Acute Toxicity:	0.152
Maximum Recommended Daily Dose:	0.137	Skin Sensitization:	0.847
Carcinogencity:	0.391	Eye Corrosion:	0.001
Eye Irritation:	0.292	Respiratory Toxicity:	0.62
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.94
Hematotoxicity:	0.358	Drug-induced Nephrotoxicity:	0.939
Genotoxicity:	0.184	RPMI-8226 Immunitoxicity:	0.048
A549 Cytotoxicity:	0.052	Hek293 Cytotoxicity:	0.043
BCF:	0.753 ? 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:	3.463 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.022 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.231 ? 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
NPO3171	Menisporopsis theobromae	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[15104506]
NPO6350	Spongia officinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548580]
NPO5813	Ligularia songarica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23043462]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24195447]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	Gum resin	n.a.	n.a.	PMID[26457560]
NPO6350	Spongia officinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[31095383]
NPO5007	Deltocyathus magnificus	Species	Caryophylliidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14881	Senecio nemorensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO460	Alangium ridleyi	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4783	Cyphus niveus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6350	Spongia officinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4658	Hedysarum denticulatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3319	Helichrysum nitens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO392	Laurencia composita	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5813	Ligularia songarica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3171	Menisporopsis theobromae	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO735	Pteraster multipes	Species	Pterasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28795	Retiboletus ornatipes	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14881	Senecio nemorensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14881	Senecio nemorensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14881	Senecio nemorensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO735	Pteraster multipes	Species	Pterasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5813	Ligularia songarica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5007	Deltocyathus magnificus	Species	Caryophylliidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO392	Laurencia composita	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4658	Hedysarum denticulatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3319	Helichrysum nitens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO460	Alangium ridleyi	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3171	Menisporopsis theobromae	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28795	Retiboletus ornatipes	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14881	Senecio nemorensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4783	Cyphus niveus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6350	Spongia officinalis	Species	Spongiidae	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 NPC222898 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	25091
0.1-0.2	21737
0.2-0.3	2481
0.3-0.4	373
0.4-0.5	138
0.5-0.6	23
0.6-0.7	9
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	Natural Product ID
0.7121	Intermediate Similarity	NPC256247
0.6923	Remote Similarity	NPC187722
0.6716	Remote Similarity	NPC173744
0.6716	Remote Similarity	NPC204961
0.6716	Remote Similarity	NPC73004
0.6567	Remote Similarity	NPC229281
0.6567	Remote Similarity	NPC194196
0.6471	Remote Similarity	NPC38754
0.6269	Remote Similarity	NPC43686
0.6232	Remote Similarity	NPC111214
0.5556	Remote Similarity	NPC73489
0.5541	Remote Similarity	NPC118964
0.5493	Remote Similarity	NPC96916
0.5417	Remote Similarity	NPC84319
0.5417	Remote Similarity	NPC52021
0.5417	Remote Similarity	NPC599947
0.5342	Remote Similarity	NPC472149
0.5342	Remote Similarity	NPC71074
0.5342	Remote Similarity	NPC37221
0.5342	Remote Similarity	NPC605937
0.527	Remote Similarity	NPC259733
0.527	Remote Similarity	NPC158371
0.527	Remote Similarity	NPC207922
0.5263	Remote Similarity	NPC284865
0.5132	Remote Similarity	NPC25299
0.5132	Remote Similarity	NPC481322
0.5132	Remote Similarity	NPC607666
0.5132	Remote Similarity	NPC608261
0.5132	Remote Similarity	NPC611078
0.5068	Remote Similarity	NPC480946
0.5068	Remote Similarity	NPC130577
0.5068	Remote Similarity	NPC142415
0.5068	Remote Similarity	NPC102683

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC222898 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6755
0.1-0.2	2355
0.2-0.3	35
0.3-0.4	5
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