NPASS Compound

Natural Product: NPC227154

Natural Product ID	NPC227154
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LFPVZIIPFONRSW-FTKVNMGKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001823] Hopanoids

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 81 85 0 0 0 0 0 0 0 0999 V2000 5.8481 0.1555 -2.0437 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0915 -0.1095 -0.7887 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4903 -0.2616 -0.3432 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0105 -0.2413 0.1835 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9389 -1.7000 0.6940 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4732 -1.9408 0.9650 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8426 -0.5618 0.9344 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1106 0.1263 2.2010 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6366 -0.0206 -0.2680 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1878 1.3818 -0.4552 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7752 1.3958 -0.9536 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8312 0.6042 -0.0742 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4388 1.5851 1.0244 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4214 -0.6384 0.4861 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5272 -1.2463 1.5304 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8657 -1.4350 1.0311 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3986 -0.3352 0.1791 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7606 -0.6782 -0.3363 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8304 -1.8722 -1.2499 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5838 -1.0939 0.8939 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0350 -1.2198 0.6121 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6030 -0.2644 -0.3622 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7018 0.9321 -0.5619 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3477 1.7454 -1.6971 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7298 1.7779 0.6468 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3635 0.5007 -1.0479 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4535 1.7116 -1.0417 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0657 1.4045 -1.5161 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4408 0.2095 -0.8392 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0911 -0.7832 -1.9268 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8374 0.2553 0.0944 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6491 0.2713 -2.7834 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8507 0.2751 -2.4923 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0713 -0.6917 -1.1835 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8999 0.7753 -0.1909 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5863 -0.8603 0.5836 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3152 0.3319 1.0856 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2300 -2.3898 -0.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5830 -1.8558 1.5574 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9791 -2.5381 0.1768 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3118 -2.4360 1.9520 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6698 -0.5486 2.9203 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2153 0.4260 2.7844 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7472 1.0342 2.1632 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4120 -0.6188 -1.1440 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8233 1.8905 -1.1907 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2404 1.9996 0.4637 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4935 2.4937 -0.9419 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7742 1.1153 -2.0045 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0579 1.1299 1.9263 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2112 2.3884 0.6199 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3869 2.1279 1.3173 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4288 -1.4105 -0.3448 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5695 -0.7442 2.5150 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9629 -2.2722 1.7361 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5144 -1.4624 1.9584 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9364 -2.4303 0.5508 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5861 0.5333 0.8850 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3368 -2.7737 -0.8767 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9311 -2.1527 -1.2741 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6084 -1.6346 -2.3106 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2311 -2.1491 1.1142 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3144 -0.5191 1.7851 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3339 -2.2613 0.2956 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5803 -1.0759 1.5911 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8250 -0.6835 -1.3654 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3135 1.1475 -2.6060 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4160 1.8692 -1.3832 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9098 2.7483 -1.7666 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9141 2.8658 0.4022 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6209 1.5052 1.2862 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8694 1.7588 1.3036 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4985 0.2603 -2.1477 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4913 2.2805 -0.0993 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8977 2.4135 -1.8117 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4781 2.3384 -1.3994 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1428 1.2673 -2.6367 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0027 -0.7478 -2.2103 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2747 -1.8273 -1.6430 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5872 -0.5102 -2.9079 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9536 -0.0368 1.0486 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 23 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 6 22 31 1 0 9 4 1 0 29 12 1 0 14 7 1 0 29 17 1 0 26 18 1 0 1 32 1 0 1 33 1 0 3 34 1 0 3 35 1 0 3 36 1 0 4 37 1 1 5 38 1 0 5 39 1 0 6 40 1 0 6 41 1 0 8 42 1 0 8 43 1 0 8 44 1 0 9 45 1 6 10 46 1 0 10 47 1 0 11 48 1 0 11 49 1 0 13 50 1 0 13 51 1 0 13 52 1 0 14 53 1 6 15 54 1 0 15 55 1 0 16 56 1 0 16 57 1 0 17 58 1 1 19 59 1 0 19 60 1 0 19 61 1 0 20 62 1 0 20 63 1 0 21 64 1 0 21 65 1 0 22 66 1 6 24 67 1 0 24 68 1 0 24 69 1 0 25 70 1 0 25 71 1 0 25 72 1 0 26 73 1 6 27 74 1 0 27 75 1 0 28 76 1 0 28 77 1 0 30 78 1 0 30 79 1 0 30 80 1 0 31 81 1 0 M END

Standard InCHIKey	LFPVZIIPFONRSW-FTKVNMGKSA-N
Standard InCHI	InChI=1S/C30H50O/c1-19(2)20-11-15-27(5)21(20)12-17-29(7)23(27)9-10-24-28(6)16-14-25(31)26(3,4)22(28)13-18-30(24,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21-,22+,23+,24+,25+,27-,28-,29+,30+/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC[C@@H]2[C@@]3(C)CC[C@H](C(C)(C)[C@H]3CC[C@@]12C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	426.39	Volume:	490.807 ? Van der Waals volume.
Dense:	0.869	LogP:	6.278 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.882 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.505 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	26.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.421	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.624	Fsp³:	0.933
MCE-18:	100.793 ? 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:	0.889	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.811	Promiscuous compounds:	0.289

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.84	MDCK Permeability:	-4.725
Pgp-inhibitor:	0.487	Pgp-substrate:	0.0
PAMPA:	0.062 ? 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%):	0.021	30% Bioavailability (F30%):	0.039
50% Bioavailability (F50%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.916	MRP1:	0.07
Plasma Protein Binding (PPB):	95.539%	Volume Distribution (VD):	-0.115
Fu:	5.203% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.995
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.144
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.359
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.35	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.952 ? 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):

17.925

Half-life (T1/2):

0.873

ADMET: Toxicity

hERG Blockers:	0.11	hERG Blockers (10um):	0.287
Human Hepatotoxicity (H-HT):	0.56	Drug-induced Liver Injury (DILI):	0.177
AMES Toxicity:	0.22	Rat Oral Acute Toxicity:	0.14
Maximum Recommended Daily Dose:	0.664	Skin Sensitization:	0.921
Carcinogencity:	0.939	Eye Corrosion:	0.597
Eye Irritation:	0.97	Respiratory Toxicity:	0.925
Drug-induced Neurotoxicity:	0.017	Ototoxicity:	0.425
Hematotoxicity:	0.544	Drug-induced Nephrotoxicity:	0.649
Genotoxicity:	0.092	RPMI-8226 Immunitoxicity:	0.034
A549 Cytotoxicity:	0.116	Hek293 Cytotoxicity:	0.492
BCF:	3.015 ? 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:	4.932 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.515 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.734 ? 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
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10514329]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10654420]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10691708]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	palauan	n.a.	PMID[10691729]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10843570]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10924172]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10978206]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076571]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076573]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076574]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11277744]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11389621]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11430000]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11473443]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11922791]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12762816]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[12828459]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14575437]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1517734]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[16643028]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17125217]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17441769]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18444683]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Singapore	n.a.	PMID[19093843]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19489598]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	eastern Caribbean	n.a.	PMID[19739598]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19839606]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20030365]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	panamanian	n.a.	PMID[20158242]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Floridian	n.a.	PMID[20166701]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20936843]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21138309]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[2128518]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21341718]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21539315]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21806011]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21999614]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22035372]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29792428]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3924698]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Caribbean	n.a.	PMID[7623050]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Caribbean	n.a.	PMID[8699186]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9584405]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9599278]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9599279]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9784156]
NPO12197	Isodon trichocarpus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12197	Isodon trichocarpus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12197	Isodon trichocarpus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25753	Goniothalamus umbrosus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26416	Colchicum visianii	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12197	Isodon trichocarpus	Species	Lamiaceae	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 NPC227154 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	26797
0.1-0.2	18981
0.2-0.3	3371
0.3-0.4	521
0.4-0.5	128
0.5-0.6	35
0.6-0.7	21
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
0.6875	Remote Similarity	NPC192638
0.6875	Remote Similarity	NPC25511
0.6875	Remote Similarity	NPC600137
0.66	Remote Similarity	NPC104387
0.6471	Remote Similarity	NPC42853
0.6471	Remote Similarity	NPC237460
0.6471	Remote Similarity	NPC231256
0.6471	Remote Similarity	NPC178383
0.64	Remote Similarity	NPC185536
0.6346	Remote Similarity	NPC93662
0.6275	Remote Similarity	NPC91573
0.6226	Remote Similarity	NPC246956
0.6226	Remote Similarity	NPC74595
0.6226	Remote Similarity	NPC264665
0.62	Remote Similarity	NPC606606
0.6154	Remote Similarity	NPC248830
0.6154	Remote Similarity	NPC212241
0.6038	Remote Similarity	NPC296701
0.6038	Remote Similarity	NPC218616
0.6	Remote Similarity	NPC12774
0.6	Remote Similarity	NPC127944
0.5926	Remote Similarity	NPC119355
0.5926	Remote Similarity	NPC269396
0.5833	Remote Similarity	NPC232112
0.5714	Remote Similarity	NPC49599
0.5714	Remote Similarity	NPC49627
0.569	Remote Similarity	NPC607755
0.5686	Remote Similarity	NPC129829
0.566	Remote Similarity	NPC144075
0.566	Remote Similarity	NPC245869
0.566	Remote Similarity	NPC301226
0.5636	Remote Similarity	NPC13554
0.5556	Remote Similarity	NPC285761
0.5556	Remote Similarity	NPC34930
0.5536	Remote Similarity	NPC126993
0.5517	Remote Similarity	NPC264317
0.5517	Remote Similarity	NPC294438
0.551	Remote Similarity	NPC11908
0.549	Remote Similarity	NPC142712
0.5455	Remote Similarity	NPC211009
0.5424	Remote Similarity	NPC33768
0.5385	Remote Similarity	NPC480925
0.5385	Remote Similarity	NPC48079
0.537	Remote Similarity	NPC78067
0.537	Remote Similarity	NPC278091
0.537	Remote Similarity	NPC240235
0.5273	Remote Similarity	NPC58631
0.5254	Remote Similarity	NPC201406
0.5185	Remote Similarity	NPC265328
0.5185	Remote Similarity	NPC97534
0.5185	Remote Similarity	NPC195155
0.5185	Remote Similarity	NPC470396
0.5179	Remote Similarity	NPC201725
0.5167	Remote Similarity	NPC112009
0.5091	Remote Similarity	NPC202540
0.5088	Remote Similarity	NPC212879

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC227154 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8043
0.1-0.2	1018
0.2-0.3	84
0.3-0.4	4
0.4-0.5	0
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
0.5517	Remote Similarity	NPD7520	Phase 1

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