NPASS Compound

Natural Product: NPC71721

Natural Product ID	NPC71721
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PYNFAPLXMQHUNR-QFPJZPNVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	59456634
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

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 105106 0 0 0 0 0 0 0 0999 V2000 12.7013 0.6356 -2.6365 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9523 1.3414 -1.3688 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8636 1.3301 -0.3598 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5840 1.9637 -0.7573 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7776 1.3557 -1.8329 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3092 -0.0503 -1.5160 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4473 0.0432 -0.2691 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9180 -1.3084 0.1639 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0749 -1.9603 -0.8792 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5968 -3.3006 -0.3976 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7989 -3.1703 0.8653 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5903 -2.2889 0.6694 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7947 -2.1869 1.9629 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5791 -1.2989 1.7762 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9855 0.1242 1.4730 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4184 0.3567 0.1143 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3667 -0.7370 -0.0463 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0198 -0.1132 0.3157 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0782 -1.1126 0.2447 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4276 -0.5448 0.5607 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5871 0.0569 1.9055 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0113 0.5336 2.1319 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3718 1.5667 1.1265 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7800 2.0607 1.3986 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7892 0.9684 1.3475 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8595 0.2472 0.0418 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1942 1.0600 -1.1445 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4465 1.8279 -1.1920 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7553 1.1766 -1.1127 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1308 0.4000 0.0884 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5434 -0.1225 -0.1481 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.6242 0.1135 0.5644 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.7956 -0.5810 0.0020 C 0 0 1 0 0 0 0 0 0 0 0 0 -14.7420 0.4983 -0.4903 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.3147 -1.2567 -1.1148 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.9623 -0.9969 -1.2266 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1966 -1.4532 -2.1367 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7369 2.2042 -1.2437 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1456 0.4167 1.6161 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7443 -1.7517 0.7923 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6098 -1.7072 2.9763 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4435 1.3336 -3.4926 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6669 0.1474 -3.0020 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0018 -0.2064 -2.5804 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2523 2.4032 -1.6307 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9079 0.9062 -0.9090 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2244 1.9258 0.5502 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7085 0.2817 0.0372 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9666 2.2644 0.1360 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8855 2.9977 -1.1644 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2929 1.3534 -2.7887 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8404 1.9825 -1.9382 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6567 -0.3690 -2.3528 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1006 -0.7814 -1.3915 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0243 0.4554 0.5822 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5499 0.6582 -0.5232 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2600 -1.1692 1.0692 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7155 -2.0086 0.4717 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1865 -1.3678 -1.1797 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6794 -2.1775 -1.8169 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9704 -3.7171 -1.2334 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4345 -4.0252 -0.2713 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4774 -4.2163 1.1566 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4019 -2.8368 1.7328 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9465 -1.2918 0.3472 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9709 -2.7211 -0.1234 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4368 -3.1883 2.2504 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0257 -1.3403 2.7397 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5577 0.8012 2.2361 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0845 0.2645 1.5242 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1685 0.3205 -0.6968 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9292 1.3520 0.0618 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3215 -1.1340 -1.0730 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1642 0.7321 -0.3588 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8954 -2.0084 0.8850 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1432 -1.4855 -0.8196 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6710 0.2026 -0.2568 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1766 -1.3667 0.3837 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3697 -0.6386 2.7356 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9765 1.0080 2.0240 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0288 0.9275 3.1822 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6580 -0.3736 2.0431 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7152 2.4771 1.2207 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2688 1.2109 0.0973 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9698 2.8732 0.6650 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7773 2.5237 2.4035 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5547 0.2147 2.1337 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8149 1.3453 1.6610 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7620 -0.0866 -0.1419 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3581 -0.7246 0.1504 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2945 1.7391 -1.3287 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1179 0.3460 -2.0366 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4544 2.6798 -0.4447 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4381 2.3885 -2.1973 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9710 0.5302 -2.0219 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5508 -0.4843 0.3336 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1977 1.0346 0.9967 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6476 0.7420 1.4534 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.2913 -1.2475 0.7414 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.7580 0.1060 -0.6778 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.2890 0.9105 -1.4195 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.7100 1.3204 0.2560 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4189 2.9315 -0.6395 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3393 1.3957 1.5679 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0843 -2.4607 3.4484 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 1 0 7 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 1 0 14 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 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 36 37 2 0 29 38 1 0 18 39 1 0 17 40 1 0 13 41 1 0 40 14 1 0 36 31 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 0 2 46 1 0 3 47 1 0 3 48 1 0 4 49 1 0 4 50 1 0 5 51 1 0 5 52 1 0 6 53 1 0 6 54 1 0 7 55 1 0 7 56 1 0 8 57 1 0 8 58 1 0 9 59 1 0 9 60 1 0 10 61 1 0 10 62 1 0 11 63 1 0 11 64 1 0 12 65 1 0 12 66 1 0 13 67 1 1 14 68 1 1 15 69 1 0 15 70 1 0 16 71 1 0 16 72 1 0 17 73 1 6 18 74 1 6 19 75 1 0 19 76 1 0 20 77 1 0 20 78 1 0 21 79 1 0 21 80 1 0 22 81 1 0 22 82 1 0 23 83 1 0 23 84 1 0 24 85 1 0 24 86 1 0 25 87 1 0 25 88 1 0 26 89 1 0 26 90 1 0 27 91 1 0 27 92 1 0 28 93 1 0 28 94 1 0 29 95 1 6 30 96 1 0 30 97 1 0 32 98 1 0 33 99 1 1 34100 1 0 34101 1 0 34102 1 0 38103 1 0 39104 1 0 41105 1 0 M END

Standard InCHIKey	PYNFAPLXMQHUNR-QFPJZPNVSA-N
Standard InCHI	InChI=1S/C35H64O6/c1-3-4-5-6-7-8-9-13-16-19-22-31(37)33-24-25-34(41-33)32(38)23-20-17-14-11-10-12-15-18-21-30(36)27-29-26-28(2)40-35(29)39/h26,28,30-34,36-38H,3-25,27H2,1-2H3/t28-,30+,31-,32-,33-,34-/m1/s1
SMILES	CCCCCCCCCCCC[C@H]([C@H]1CC[C@H]([C@@H](CCCCCCCCCC[C@@H](CC2=C[C@@H](C)OC2=O)O)O)O1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	580.47	Volume:	644.271 ? Van der Waals volume.
Dense:	0.901	LogP:	6.728 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.13 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.01 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	26.0	Rigid Bonds:	11.0
TPSA:	96.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	2.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.071	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.401	Fsp³:	0.914
MCE-18:	30.09 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.79	Fluc inhibitor:	0.164 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.076 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.595	Promiscuous compounds:	0.265

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.154	MDCK Permeability:	-4.85
Pgp-inhibitor:	0.001	Pgp-substrate:	0.849
PAMPA:	0.049 ? 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):	0.073
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.99
Plasma Protein Binding (PPB):	96.998%	Volume Distribution (VD):	0.731
Fu:	3.071% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.746
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.749
BSEP inhibitor:	0.972

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.004	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.998	CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.105	CYP2D6-substrate:	0.967
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.977
HLM stability:	0.001 ? 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):

5.068

Half-life (T1/2):

1.276

ADMET: Toxicity

hERG Blockers:	0.533	hERG Blockers (10um):	0.787
Human Hepatotoxicity (H-HT):	0.596	Drug-induced Liver Injury (DILI):	0.096
AMES Toxicity:	0.067	Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.718	Skin Sensitization:	0.999
Carcinogencity:	0.336	Eye Corrosion:	0.228
Eye Irritation:	0.953	Respiratory Toxicity:	0.982
Drug-induced Neurotoxicity:	0.034	Ototoxicity:	0.553
Hematotoxicity:	0.126	Drug-induced Nephrotoxicity:	0.849
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.082
A549 Cytotoxicity:	0.991	Hek293 Cytotoxicity:	0.366
BCF:	0.831 ? 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:	4.768 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.266 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.472 ? 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 NPC71721 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	15361
0.1-0.2	30448
0.2-0.3	3648
0.3-0.4	154
0.4-0.5	32
0.5-0.6	13
0.6-0.7	49
0.7-0.8	0
0.8-0.85	14
0.85-0.9	32
0.9-0.95	13
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC606043
0.975	High Similarity	NPC107986
0.975	High Similarity	NPC223871
0.975	High Similarity	NPC231009
0.975	High Similarity	NPC103284
0.975	High Similarity	NPC110710
0.975	High Similarity	NPC1083
0.975	High Similarity	NPC82795
0.975	High Similarity	NPC286338
0.975	High Similarity	NPC603931
0.975	High Similarity	NPC604237
0.9512	High Similarity	NPC488253
0.9512	High Similarity	NPC473669
0.9512	High Similarity	NPC488251
0.9286	High Similarity	NPC232555
0.9286	High Similarity	NPC171174
0.9286	High Similarity	NPC114694
0.9286	High Similarity	NPC485248
0.9286	High Similarity	NPC142117
0.9286	High Similarity	NPC480249
0.9286	High Similarity	NPC485249
0.9286	High Similarity	NPC240695
0.907	High Similarity	NPC488632
0.907	High Similarity	NPC134865
0.907	High Similarity	NPC103523
0.907	High Similarity	NPC488627
0.907	High Similarity	NPC488631
0.8864	High Similarity	NPC280621
0.8864	High Similarity	NPC48338
0.8864	High Similarity	NPC488628
0.8837	High Similarity	NPC81045
0.8837	High Similarity	NPC39754
0.8837	High Similarity	NPC171135
0.8837	High Similarity	NPC182383
0.8837	High Similarity	NPC61257
0.8837	High Similarity	NPC320569
0.8837	High Similarity	NPC133730
0.8837	High Similarity	NPC191929
0.8837	High Similarity	NPC100454
0.8837	High Similarity	NPC242364
0.8837	High Similarity	NPC172821
0.8837	High Similarity	NPC274446
0.8837	High Similarity	NPC485251
0.8837	High Similarity	NPC151403
0.8837	High Similarity	NPC261952
0.8837	High Similarity	NPC605171
0.8667	High Similarity	NPC178215
0.8667	High Similarity	NPC473687
0.8667	High Similarity	NPC204686
0.8667	High Similarity	NPC219498
0.8667	High Similarity	NPC308412
0.8667	High Similarity	NPC134885
0.8667	High Similarity	NPC488247
0.8667	High Similarity	NPC210218
0.8667	High Similarity	NPC488248
0.8636	High Similarity	NPC93794
0.8636	High Similarity	NPC473504
0.8636	High Similarity	NPC81778
0.8636	High Similarity	NPC40066
0.8478	Intermediate Similarity	NPC20621
0.8478	Intermediate Similarity	NPC318963
0.8478	Intermediate Similarity	NPC488250
0.8478	Intermediate Similarity	NPC605101
0.8298	Intermediate Similarity	NPC69082
0.8298	Intermediate Similarity	NPC488249
0.8261	Intermediate Similarity	NPC42598
0.8222	Intermediate Similarity	NPC47937
0.8222	Intermediate Similarity	NPC477011
0.8125	Intermediate Similarity	NPC130359
0.8125	Intermediate Similarity	NPC14901
0.8085	Intermediate Similarity	NPC134807
0.8085	Intermediate Similarity	NPC602738
0.8	Intermediate Similarity	NPC608138
0.7959	Intermediate Similarity	NPC488623
0.7959	Intermediate Similarity	NPC488624
0.7959	Intermediate Similarity	NPC488629
0.7955	Intermediate Similarity	NPC100921
0.7955	Intermediate Similarity	NPC475159
0.7955	Intermediate Similarity	NPC131002
0.7955	Intermediate Similarity	NPC473780
0.7955	Intermediate Similarity	NPC477018
0.7955	Intermediate Similarity	NPC604521
0.7917	Intermediate Similarity	NPC473478
0.7917	Intermediate Similarity	NPC473651
0.7917	Intermediate Similarity	NPC66346
0.7907	Intermediate Similarity	NPC112685
0.7755	Intermediate Similarity	NPC283085
0.7755	Intermediate Similarity	NPC169511
0.7755	Intermediate Similarity	NPC287164
0.7755	Intermediate Similarity	NPC234077
0.7674	Intermediate Similarity	NPC73310
0.7674	Intermediate Similarity	NPC473529
0.7674	Intermediate Similarity	NPC180363
0.7674	Intermediate Similarity	NPC94875
0.7674	Intermediate Similarity	NPC11332
0.7674	Intermediate Similarity	NPC145914
0.7674	Intermediate Similarity	NPC601174
0.7674	Intermediate Similarity	NPC601403
0.7674	Intermediate Similarity	NPC603568
0.7674	Intermediate Similarity	NPC604330
0.7674	Intermediate Similarity	NPC608300
0.7674	Intermediate Similarity	NPC611200
0.7674	Intermediate Similarity	NPC611571
0.7647	Intermediate Similarity	NPC488630
0.7647	Intermediate Similarity	NPC488625
0.7647	Intermediate Similarity	NPC488626
0.7609	Intermediate Similarity	NPC156804
0.7451	Intermediate Similarity	NPC239517
0.7447	Intermediate Similarity	NPC163093
0.74	Intermediate Similarity	NPC231096
0.74	Intermediate Similarity	NPC475581
0.74	Intermediate Similarity	NPC62118
0.74	Intermediate Similarity	NPC132496
0.74	Intermediate Similarity	NPC107717
0.74	Intermediate Similarity	NPC488252
0.7308	Intermediate Similarity	NPC91067
0.7255	Intermediate Similarity	NPC233551
0.7255	Intermediate Similarity	NPC40376
0.7255	Intermediate Similarity	NPC21208
0.72	Intermediate Similarity	NPC20339
0.7174	Intermediate Similarity	NPC329829
0.7083	Intermediate Similarity	NPC473649
0.7083	Intermediate Similarity	NPC473156
0.7083	Intermediate Similarity	NPC154097
0.7083	Intermediate Similarity	NPC159750
0.7083	Intermediate Similarity	NPC73248
0.7083	Intermediate Similarity	NPC282815
0.7083	Intermediate Similarity	NPC470401
0.7083	Intermediate Similarity	NPC600956
0.7083	Intermediate Similarity	NPC610454
0.7059	Intermediate Similarity	NPC606740
0.7059	Intermediate Similarity	NPC608614
0.7037	Intermediate Similarity	NPC473663
0.7037	Intermediate Similarity	NPC473723
0.7037	Intermediate Similarity	NPC475173
0.7	Intermediate Similarity	NPC309211
0.7	Intermediate Similarity	NPC329838
0.7	Intermediate Similarity	NPC477010
0.6981	Remote Similarity	NPC480081
0.6939	Remote Similarity	NPC473671
0.6939	Remote Similarity	NPC475268
0.6939	Remote Similarity	NPC470400
0.6939	Remote Similarity	NPC77871
0.6939	Remote Similarity	NPC9678
0.6939	Remote Similarity	NPC319036
0.6939	Remote Similarity	NPC604764
0.6939	Remote Similarity	NPC605867
0.6809	Remote Similarity	NPC25764
0.6809	Remote Similarity	NPC235809
0.6809	Remote Similarity	NPC39279
0.6809	Remote Similarity	NPC39167
0.6809	Remote Similarity	NPC292809
0.6809	Remote Similarity	NPC202055
0.6809	Remote Similarity	NPC606804
0.6809	Remote Similarity	NPC607425
0.6809	Remote Similarity	NPC608574
0.68	Remote Similarity	NPC132940
0.6735	Remote Similarity	NPC144415
0.6735	Remote Similarity	NPC607439
0.6735	Remote Similarity	NPC608157
0.6731	Remote Similarity	NPC258068
0.6731	Remote Similarity	NPC476583
0.6667	Remote Similarity	NPC20533
0.6604	Remote Similarity	NPC477014
0.6604	Remote Similarity	NPC477013
0.66	Remote Similarity	NPC241360
0.66	Remote Similarity	NPC293136
0.66	Remote Similarity	NPC480079
0.6491	Remote Similarity	NPC482766
0.6491	Remote Similarity	NPC279267
0.6471	Remote Similarity	NPC473904
0.6415	Remote Similarity	NPC120398
0.6415	Remote Similarity	NPC471567
0.64	Remote Similarity	NPC488246
0.64	Remote Similarity	NPC480080
0.64	Remote Similarity	NPC600524
0.64	Remote Similarity	NPC608355
0.6296	Remote Similarity	NPC89001
0.6275	Remote Similarity	NPC219652
0.6275	Remote Similarity	NPC473840
0.6226	Remote Similarity	NPC473707
0.6226	Remote Similarity	NPC11456
0.6226	Remote Similarity	NPC477012
0.6154	Remote Similarity	NPC65930
0.6071	Remote Similarity	NPC280612
0.6038	Remote Similarity	NPC485250
0.6038	Remote Similarity	NPC605396
0.5962	Remote Similarity	NPC25703
0.5932	Remote Similarity	NPC477017
0.5932	Remote Similarity	NPC477016
0.5818	Remote Similarity	NPC473995
0.5818	Remote Similarity	NPC488244
0.5741	Remote Similarity	NPC329615
0.569	Remote Similarity	NPC477015
0.5652	Remote Similarity	NPC609415
0.5636	Remote Similarity	NPC139418
0.5517	Remote Similarity	NPC473520
0.5472	Remote Similarity	NPC482767
0.5472	Remote Similarity	NPC475260
0.5472	Remote Similarity	NPC488621

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC71721 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6099
0.1-0.2	2959
0.2-0.3	91
0.3-0.4	1
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