NPASS Compound

Natural Product: NPC183815

Natural Product ID	NPC183815
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SZCBXWMUOPQSOX-LOIAFDEVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	53477762
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001554] Tetraterpenoids [CHEMONTID:0001277] Carotenoids [CHEMONTID:0001410] Xanthophylls

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 100103 0 0 0 0 0 0 0 0999 V2000 2.6017 0.4009 0.3690 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0153 1.4645 -0.7371 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9947 1.8404 -1.3661 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6320 1.4144 -1.0814 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4055 1.6362 -1.8743 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7080 1.2128 -1.4787 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8132 1.1420 -2.1730 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7874 1.5011 -3.6117 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1022 1.0329 -1.5293 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1899 0.8099 -2.1811 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4824 0.7237 -1.5833 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6554 0.3984 -1.9353 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8483 -0.0341 -3.3514 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7948 0.3897 -0.9798 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9689 0.0371 -1.3750 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2106 -0.0291 -0.5072 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.0311 0.2044 0.9505 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9026 -0.7145 1.4720 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6263 1.6374 1.2141 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2300 -0.0422 1.8304 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1978 -1.0651 1.4088 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9735 -1.7040 0.0985 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1954 -0.9583 -0.9351 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.0380 -1.7702 -2.2271 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3889 0.3892 -1.0897 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.4942 -0.5049 1.5271 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2851 2.0474 -0.3342 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2143 1.2026 0.0750 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5341 1.2926 0.5915 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2829 0.2529 0.7549 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8025 -1.1026 0.4167 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6240 0.4465 1.3499 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4375 -0.5903 1.4888 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7716 -0.4345 2.0838 C 0 0 1 0 0 0 0 0 0 0 0 0 11.5974 -1.6268 2.0501 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1997 -2.0688 3.3321 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7875 -2.8399 1.5356 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6311 -1.4171 0.9422 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0318 -0.5520 -0.1761 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6089 0.8141 0.3251 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6443 0.7733 1.7811 C 0 0 2 0 0 0 0 0 0 0 0 0 12.9789 1.0759 2.3754 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7865 0.6917 2.7906 O 0 0 0 0 0 0 0 0 0 0 0 0 12.9851 -0.5270 -1.1663 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9850 1.0120 1.0869 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4872 0.0952 0.8938 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0098 -0.3467 -0.1276 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1713 2.5637 -2.1740 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4356 0.8945 -0.1662 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1522 2.1368 -2.8210 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7965 0.9075 -0.4011 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2102 0.5973 -4.1401 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7501 1.6612 -3.9432 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4419 2.3603 -3.8765 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1279 1.1508 -0.4288 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1076 0.6941 -3.2630 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4493 1.0430 -0.4599 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0236 0.2582 -4.0200 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9215 -1.1618 -3.4091 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7895 0.4421 -3.7450 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6248 0.6901 0.0158 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1003 -0.2261 -2.4130 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3998 -1.2624 0.6774 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1808 -0.1859 2.1133 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4210 -1.4687 2.1645 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6000 1.7416 1.6257 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3045 2.1082 2.0071 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7503 2.2930 0.3550 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7674 -0.3986 2.8173 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6866 0.9309 2.1467 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2197 -1.9205 2.1541 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.9972 -1.8749 -0.3813 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5925 -2.7706 0.1910 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3435 -2.6220 -2.0934 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7576 -1.1166 -3.0547 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0321 -2.2001 -2.5126 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.6205 0.2013 0.8305 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5211 3.0600 -0.3174 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8787 0.1547 -0.2521 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8996 2.3048 0.8379 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7229 -1.2177 0.7758 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8014 -1.3676 -0.6311 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2921 -1.9080 1.0243 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8869 1.4404 1.6795 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0571 -1.5168 1.1053 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9111 -1.4773 4.2240 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0914 -3.1910 3.4982 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3466 -1.9998 3.3540 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9274 -3.0454 2.1701 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5070 -3.7063 1.6703 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5983 -2.7825 0.4451 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8622 -2.3822 0.3948 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5912 -1.0682 1.3078 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1848 -1.1525 -0.5827 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7164 1.1996 -0.1703 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4372 1.4971 -0.0548 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7666 1.2190 1.6253 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8809 2.1066 2.8399 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2859 0.4544 3.2208 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5106 0.3015 -1.0570 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 12 14 1 0 14 15 2 0 16 15 1 6 16 17 1 0 17 18 1 0 17 19 1 0 17 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 23 25 1 0 21 26 1 0 2 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 30 32 1 0 32 33 2 0 34 33 1 6 34 35 1 0 35 36 1 0 35 37 1 0 35 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 1 41 43 1 0 39 44 1 0 23 16 1 0 41 34 1 0 25 16 1 0 43 34 1 0 1 45 1 0 1 46 1 0 1 47 1 0 3 48 1 0 4 49 1 0 5 50 1 0 6 51 1 0 8 52 1 0 8 53 1 0 8 54 1 0 9 55 1 0 10 56 1 0 11 57 1 0 13 58 1 0 13 59 1 0 13 60 1 0 14 61 1 0 15 62 1 0 18 63 1 0 18 64 1 0 18 65 1 0 19 66 1 0 19 67 1 0 19 68 1 0 20 69 1 0 20 70 1 0 21 71 1 0 22 72 1 0 22 73 1 0 24 74 1 0 24 75 1 0 24 76 1 0 26 77 1 0 27 78 1 0 28 79 1 0 29 80 1 0 31 81 1 0 31 82 1 0 31 83 1 0 32 84 1 0 33 85 1 0 36 86 1 0 36 87 1 0 36 88 1 0 37 89 1 0 37 90 1 0 37 91 1 0 38 92 1 0 38 93 1 0 39 94 1 0 40 95 1 0 40 96 1 0 42 97 1 0 42 98 1 0 42 99 1 0 44100 1 0 M END

Standard InCHIKey	SZCBXWMUOPQSOX-LOIAFDEVSA-N
Standard InCHI	InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33?,34?,37-,38-,39-,40+/m1/s1
SMILES	C/C(=CC=CC=C(/C)C=CC=C(/C)C=C[C@]12C(C)(C)CC(C[C@@]1(C)O2)O)/C=C/C=C(C)/C=C/[C@@]12C(C)(C)CC(C[C@@]1(C)O2)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	600.42	Volume:	677.603 ? Van der Waals volume.
Dense:	0.886	LogP:	5.22 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.093 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.091 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	25.0
TPSA:	65.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.194	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.425	Fsp³:	0.55
MCE-18:	85.935 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.999	Fluc inhibitor:	0.05 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.309 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.601	Promiscuous compounds:	0.09

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.953	MDCK Permeability:	-4.754
Pgp-inhibitor:	0.031	Pgp-substrate:	0.972
PAMPA:	0.984 ? 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%):	0.837	30% Bioavailability (F30%):	0.871
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.943
Plasma Protein Binding (PPB):	85.563%	Volume Distribution (VD):	0.132
Fu:	11.222% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.077
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.018	CYP1A2-substrate:	0.682
CYP2C19-inhibitor:	0.004	CYP2C19-substrate:	0.124
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.005	CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.048	CYP3A4-substrate:	0.978
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.289 ? 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):

10.536

Half-life (T1/2):

0.705

ADMET: Toxicity

hERG Blockers:	0.15	hERG Blockers (10um):	0.596
Human Hepatotoxicity (H-HT):	0.337	Drug-induced Liver Injury (DILI):	0.078
AMES Toxicity:	0.68	Rat Oral Acute Toxicity:	0.842
Maximum Recommended Daily Dose:	0.837	Skin Sensitization:	0.798
Carcinogencity:	0.828	Eye Corrosion:	0.0
Eye Irritation:	0.107	Respiratory Toxicity:	0.406
Drug-induced Neurotoxicity:	0.485	Ototoxicity:	0.853
Hematotoxicity:	0.088	Drug-induced Nephrotoxicity:	0.65
Genotoxicity:	0.639	RPMI-8226 Immunitoxicity:	0.115
A549 Cytotoxicity:	0.036	Hek293 Cytotoxicity:	0.612
BCF:	2.474 ? 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:	4.599 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.446 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.919 ? 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
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11356-018-3422-z]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2020.113007]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1246/bcsj.30.618]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.3923/pjbs.2013.1138.1144]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15516765]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[17190444]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17262437]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18326559]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20973550]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22305790]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Essential oil	n.a.	n.a.	PMID[23163425]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327299]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23700450]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23849114]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23865201]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24310066]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	bulb	n.a.	PMID[24508058]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25433632]
NPO26488	Tagetes patula	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[25539472]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25650289]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	garlic skin	n.a.	n.a.	PMID[25726329]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[26860358]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466882]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35143705]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36235013]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36235241]
NPO26488	Tagetes patula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36364067]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36378844]
NPO23017	Urtica dioica	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36447306]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37241721]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38139796]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38498554]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38792127]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38986200]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39409699]
NPO23017	Urtica dioica	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39696148]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350088]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13418	Rumex acetosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23017	Urtica dioica	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6956	Citrus limonia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26488	Tagetes patula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13418	Rumex acetosa	Species	Polygonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Bulb	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO13418	Rumex acetosa	Species	Polygonaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Protoplast	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO13418	Rumex acetosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26488	Tagetes patula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6956	Citrus limonia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13418	Rumex acetosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23017	Urtica dioica	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6956	Citrus limonia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23017	Urtica dioica	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26488	Tagetes patula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13418	Rumex acetosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23017	Urtica dioica	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6956	Citrus limonia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26488	Tagetes patula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6956	Citrus limonia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27261	Carica papaya	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13418	Rumex acetosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26488	Tagetes patula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28919	Calendula officinalis	Species	Asteraceae	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 NPC183815 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	23967
0.1-0.2	25469
0.2-0.3	390
0.3-0.4	24
0.4-0.5	7
0.5-0.6	1
0.6-0.7	1
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
0.6	Remote Similarity	NPC259858
0.5714	Remote Similarity	NPC103014

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC183815 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7733
0.1-0.2	1399
0.2-0.3	14
0.3-0.4	3
0.4-0.5	1
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