NPASS Compound

Natural Product: NPC64217

Natural Product ID	NPC64217
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KFJDDTQQIDDGCC-BURHBHQASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	14395311
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids

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 83 86 0 0 0 0 0 0 0 0999 V2000 -6.1736 1.1695 1.6435 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6943 1.4240 1.3249 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0883 0.0972 0.8693 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2803 -0.8520 2.0641 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0098 -0.4300 -0.2091 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4815 -1.6891 -0.7843 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9751 -1.7884 -0.8300 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3157 -0.4094 -0.8640 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8704 0.3078 -2.0380 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6744 0.2293 0.4725 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1104 1.6199 0.5202 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5978 1.4690 0.6069 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0602 0.6890 -0.6046 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0282 1.6351 -1.7349 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3310 0.2220 -0.1482 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1212 1.2939 0.5012 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6085 1.2314 0.2506 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1665 -0.1123 0.0554 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2422 -1.1928 -0.4018 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0474 -0.6094 -1.1447 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4587 -0.0117 -2.4122 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1343 -1.8061 -1.4651 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2196 -1.3157 -1.9780 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8405 -0.5751 -0.8357 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8628 -2.3998 -0.1917 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1742 -3.6883 0.1287 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7297 -4.4135 -0.7228 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8634 -4.2427 1.4733 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8792 -0.6168 1.2670 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5063 -1.6112 1.8710 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0761 0.0887 1.7718 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2622 1.9030 1.3066 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9623 3.0757 1.0826 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0112 3.5491 -0.1035 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6660 3.8192 2.1586 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5090 2.0470 2.2456 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2833 0.2738 2.2847 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7904 1.1463 0.7372 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6429 2.2023 0.5663 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2355 1.7050 2.3066 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1774 -0.3105 3.0222 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4322 -1.5870 2.0327 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2027 -1.4304 1.9854 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2966 0.3508 -0.9223 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9693 -0.6934 0.3321 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8238 -2.5701 -0.1652 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9585 -1.8471 -1.7767 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7487 -2.2758 -1.8244 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5470 -2.4241 -0.0511 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2922 1.2947 -1.8447 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6814 -0.2717 -2.5754 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0778 0.3965 -2.8389 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0652 -0.3544 1.2308 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4397 2.2802 -0.2754 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4139 2.0821 1.4835 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3422 0.9747 1.5536 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1873 2.4916 0.5802 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1535 1.2455 -2.7295 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7743 2.3912 -1.5373 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9799 2.2452 -1.6968 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0587 -0.5125 0.6793 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0015 1.2937 1.6273 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8113 2.3353 0.2154 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8216 1.8483 -0.6668 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9825 -0.0750 -0.7336 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7648 -1.9509 -0.9930 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8451 -1.6958 0.5186 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8328 -0.3780 -3.2807 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -0.4026 -2.6729 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5238 1.0639 -2.5031 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6176 -2.5054 -2.1443 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1363 -0.7582 -2.9109 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7641 -2.2629 -2.2380 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6293 -1.2119 0.0812 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2962 -3.4829 2.0530 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3248 -5.2090 1.4182 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8382 -4.3606 2.0074 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5860 0.6962 0.9851 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8602 -0.6212 2.1298 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8210 0.7651 2.6000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4762 4.4249 1.7028 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9023 4.4521 2.6551 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1630 3.1254 2.8658 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 1 3 4 1 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 6 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 22 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 18 29 1 0 29 30 2 0 29 31 1 0 17 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 10 3 1 0 24 13 1 0 24 8 1 0 20 15 1 0 1 36 1 0 1 37 1 0 1 38 1 0 2 39 1 0 2 40 1 0 4 41 1 0 4 42 1 0 4 43 1 0 5 44 1 0 5 45 1 0 6 46 1 0 6 47 1 0 7 48 1 0 7 49 1 0 9 50 1 0 9 51 1 0 9 52 1 0 10 53 1 1 11 54 1 0 11 55 1 0 12 56 1 0 12 57 1 0 14 58 1 0 14 59 1 0 14 60 1 0 15 61 1 1 16 62 1 0 16 63 1 0 17 64 1 6 18 65 1 6 19 66 1 0 19 67 1 0 21 68 1 0 21 69 1 0 21 70 1 0 22 71 1 6 23 72 1 0 23 73 1 0 24 74 1 1 28 75 1 0 28 76 1 0 28 77 1 0 31 78 1 0 31 79 1 0 31 80 1 0 35 81 1 0 35 82 1 0 35 83 1 0 M END

Standard InCHIKey	KFJDDTQQIDDGCC-BURHBHQASA-N
Standard InCHI	InChI=1S/C30H48O5/c1-9-27(5)12-10-13-28(6)23(27)11-14-29(7)24-15-22(34-19(3)32)21(18(2)31)17-30(24,8)26(16-25(28)29)35-20(4)33/h21-26H,9-17H2,1-8H3/t21-,22-,23+,24+,25-,26+,27+,28+,29+,30-/m1/s1
SMILES	CC[C@@]1(C)CCC[C@@]2(C)[C@H]1CC[C@@]1(C)[C@@H]3C[C@H]([C@H](C[C@@]3(C)[C@H](C[C@H]21)OC(=O)C)C(=O)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.35	Volume:	529.252 ? Van der Waals volume.
Dense:	0.923	LogP:	4.543 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.654 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.671 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	24.0
TPSA:	69.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.422	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.923	Fsp³:	0.9
MCE-18:	86.842 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.847	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? 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:	0.574	Promiscuous compounds:	0.638

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.687	MDCK Permeability:	-4.766
Pgp-inhibitor:	0.962	Pgp-substrate:	0.01
PAMPA:	0.014 ? 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%):	0.111	30% Bioavailability (F30%):	0.53
50% Bioavailability (F50%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.817	MRP1:	0.913
Plasma Protein Binding (PPB):	87.352%	Volume Distribution (VD):	0.35
Fu:	10.239% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.566
BSEP inhibitor:	0.982

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.012
CYP2C19-inhibitor:	0.94	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.993
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.339 ? 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):

10.395

Half-life (T1/2):

0.369

ADMET: Toxicity

hERG Blockers:	0.104	hERG Blockers (10um):	0.362
Human Hepatotoxicity (H-HT):	0.58	Drug-induced Liver Injury (DILI):	0.538
AMES Toxicity:	0.446	Rat Oral Acute Toxicity:	0.335
Maximum Recommended Daily Dose:	0.599	Skin Sensitization:	0.988
Carcinogencity:	0.882	Eye Corrosion:	0.353
Eye Irritation:	0.773	Respiratory Toxicity:	0.735
Drug-induced Neurotoxicity:	0.071	Ototoxicity:	0.174
Hematotoxicity:	0.719	Drug-induced Nephrotoxicity:	0.49
Genotoxicity:	0.293	RPMI-8226 Immunitoxicity:	0.039
A549 Cytotoxicity:	0.363	Hek293 Cytotoxicity:	0.538
BCF:	1.524 ? 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:	4.545 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.011 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.562 ? 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
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	Niphates recondita	Weizhou Island, Beibuwan Bay, Guangxi,China	n.a.	PMID[24387683]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24387683]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28530828]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31265296]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32966070]
NPO12586	Tapirira guianensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9514013]
NPO9147	Frasera albomarginata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28504	Calothrix brevissima	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3308	Calycadenia fremontii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12931	Carex pumila	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8395.1	Crepis foetida subsp. rhoeadifolia	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13038	Fomes hartigii	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12586	Tapirira guianensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8857	Hydnum repandum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10944	Mantella baroni	Species	Mantellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7116	Monachosorum henryi	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2431	Penicilliopsis zonata	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9355	Polygonatum orientale	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9977	Polygonum sieboldi	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12364	Polyides rotundus	Species	Polyideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12708	Rothia indica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6781	Senecio acanthifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5958	Senegalia modesta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5472	Spongia foliascens	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7116	Monachosorum henryi	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8857	Hydnum repandum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9147	Frasera albomarginata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9355	Polygonatum orientale	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12708	Rothia indica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13038	Fomes hartigii	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28504	Calothrix brevissima	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8857	Hydnum repandum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9977	Polygonum sieboldi	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7116	Monachosorum henryi	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3308	Calycadenia fremontii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5958	Senegalia modesta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12364	Polyides rotundus	Species	Polyideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12931	Carex pumila	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8395.1	Crepis foetida subsp. rhoeadifolia	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10944	Mantella baroni	Species	Mantellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6781	Senecio acanthifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2431	Penicilliopsis zonata	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5472	Spongia foliascens	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12586	Tapirira guianensis	Species	Anacardiaceae	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 NPC64217 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	23257
0.1-0.2	24093
0.2-0.3	2352
0.3-0.4	113
0.4-0.5	32
0.5-0.6	7
0.6-0.7	3
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
0.6786	Remote Similarity	NPC237938
0.6491	Remote Similarity	NPC9060
0.6034	Remote Similarity	NPC269121
0.5902	Remote Similarity	NPC474572
0.5538	Remote Similarity	NPC88337
0.55	Remote Similarity	NPC219535
0.5484	Remote Similarity	NPC3032
0.541	Remote Similarity	NPC601034
0.5294	Remote Similarity	NPC475211
0.5246	Remote Similarity	NPC181871

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC64217 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6943
0.1-0.2	2155
0.2-0.3	52
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