NPASS Compound

Natural Product: NPC128828

Natural Product ID	NPC128828
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Halocynthiaxanthin
IUPAC Name	(3E,5E,7E,9E,11E,13E,15E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-1-[(1R,3S,6S)-3-hydroxy-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-6-yl]-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15-heptaen-17-yn-2-one
Synonyms	Halocynthia Xanthin; Halocynthiaxanthin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL450953
PubChem CID	11966451
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 98100 0 0 0 0 0 0 0 0999 V2000 -2.8243 -0.8306 -0.7992 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3985 0.5866 -0.9444 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3918 1.5276 -0.9796 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0885 0.9098 -0.8538 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0345 0.6154 -0.7203 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3041 0.1623 -0.5807 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4746 0.8253 -0.4324 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5243 2.2580 -0.4354 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5991 -0.1245 -0.1735 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8017 0.3107 0.0799 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0675 -0.0366 0.3510 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0794 0.8262 0.6691 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7600 2.2520 0.7285 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3609 0.2385 0.9486 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5360 -1.0813 0.8040 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5581 0.9241 1.3933 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8364 0.1326 1.1504 C 0 0 2 0 0 0 0 0 0 0 0 0 12.0931 0.7862 1.6998 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9784 -0.2723 2.3697 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6452 1.6820 2.8960 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8420 1.6139 0.7534 C 0 0 0 0 0 0 0 0 0 0 0 0 13.2273 0.9169 -0.5161 C 0 0 1 0 0 0 0 0 0 0 0 0 12.5069 -0.4137 -0.6662 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0565 -0.2964 -0.2185 C 0 0 2 0 0 0 0 0 0 0 0 0 10.0379 -0.0620 -1.2807 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7552 -1.2069 0.8445 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8342 1.7661 -1.6012 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7566 0.7880 -0.9081 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6514 -0.3429 -0.7109 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9939 0.1633 -0.7042 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9620 -0.8087 -0.4804 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0071 -2.2025 -0.3424 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1172 -0.9141 -0.2908 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4628 -1.0363 -0.0941 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9097 -1.1752 0.0962 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5143 -1.5278 1.1037 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7040 -1.9276 2.3871 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.9691 -1.5807 1.1998 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.4757 -2.0450 -0.1511 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.0239 -1.1455 -1.2684 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.6131 -0.7799 -1.2276 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8109 -1.4471 -2.3199 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3944 0.7333 -1.3909 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.8576 -2.1509 -0.1540 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5482 -1.5480 -0.4475 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0473 -0.7596 -0.0120 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4521 -1.1691 -1.7705 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6750 2.5103 -1.1108 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6267 2.2708 -0.4670 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3346 -0.6553 -1.3207 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4951 -0.9728 -0.5158 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0039 2.6228 0.4844 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5852 2.7578 -0.7150 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2150 2.5697 -1.3028 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5427 -1.1732 -0.1381 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6928 1.5335 0.0274 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3780 -1.1190 0.3354 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9316 2.3212 1.4943 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4714 2.7294 -0.2048 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5895 2.8206 1.2376 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6877 1.9166 0.8543 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4445 1.1696 2.5096 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8159 -0.3038 3.4907 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0498 -0.1183 2.2495 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7585 -1.2794 1.9872 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5611 2.0540 3.3796 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2105 0.9471 3.6607 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0181 2.4691 2.5624 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7666 2.0423 1.2475 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2560 2.5419 0.4990 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3050 0.7440 -0.6371 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5183 -0.6316 -1.7448 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1090 -1.1845 -0.1953 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5954 0.2361 -2.2604 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4867 -1.0031 -1.5851 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3299 0.7625 -1.0960 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0464 1.3216 -2.4804 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3368 1.6856 -1.0687 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1825 -1.1897 -0.6422 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4358 1.0932 -0.7933 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4430 -2.0477 0.5177 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6510 -2.3397 -1.3174 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8467 -2.9414 -0.1742 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4008 -1.6001 3.2757 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7733 -1.4026 2.4456 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4967 -2.9897 2.3844 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.3240 -2.2759 1.9726 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.3156 -0.5440 1.4276 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.9982 -3.0512 -0.3410 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.3693 -1.6111 -2.2460 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.6111 -0.1715 -1.2604 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4197 -1.7588 -3.2031 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2996 -2.3526 -1.8741 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0040 -0.7497 -2.6314 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3694 1.2292 -1.0816 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5575 1.0681 -0.7248 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2014 1.0179 -2.4398 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.1313 -2.8141 0.5283 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 14 16 1 0 17 16 1 6 17 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 22 27 1 0 2 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 31 33 1 0 33 34 3 0 34 35 1 0 35 36 2 0 36 37 1 0 36 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 41 43 1 0 39 44 1 0 24 17 1 0 41 35 1 0 26 17 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 16 61 1 0 16 62 1 0 19 63 1 0 19 64 1 0 19 65 1 0 20 66 1 0 20 67 1 0 20 68 1 0 21 69 1 0 21 70 1 0 22 71 1 1 23 72 1 0 23 73 1 0 25 74 1 0 25 75 1 0 25 76 1 0 27 77 1 0 28 78 1 0 29 79 1 0 30 80 1 0 32 81 1 0 32 82 1 0 32 83 1 0 37 84 1 0 37 85 1 0 37 86 1 0 38 87 1 0 38 88 1 0 39 89 1 6 40 90 1 0 40 91 1 0 42 92 1 0 42 93 1 0 42 94 1 0 43 95 1 0 43 96 1 0 43 97 1 0 44 98 1 0 M END

Standard InCHIKey	CNOIXMULOQWVGR-ABUIXNMTSA-N
Standard InCHI	InChI=1S/C40H54O4/c1-28(17-13-18-30(3)21-22-35-32(5)23-33(41)24-37(35,6)7)15-11-12-16-29(2)19-14-20-31(4)36(43)27-40-38(8,9)25-34(42)26-39(40,10)44-40/h11-20,33-34,41-42H,23-27H2,1-10H3/b12-11+,17-13+,19-14+,28-15+,29-16+,30-18+,31-20+/t33-,34+,39-,40+/m1/s1
SMILES	C/C(=CC=CC=C(/C)C=CC=C(/C)C(=O)C[C@]12C(C)(C)C[C@@H](C[C@@]1(C)O2)O)/C=C/C=C(C)/C#CC1=C(C)C[C@H](CC1(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	598.4	Volume:	680.886 ? Van der Waals volume.
Dense:	0.879	LogP:	4.323 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.689 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.326 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	23.0
TPSA:	70.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.121	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.434	Fsp³:	0.525
MCE-18:	69.836 ? 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:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	1.0	Fluc inhibitor:	0.438 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.213 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.41 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.571	Promiscuous compounds:	0.319

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.987	MDCK Permeability:	-4.745
Pgp-inhibitor:	0.262	Pgp-substrate:	0.9
PAMPA:	0.988 ? 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%):	0.557	30% Bioavailability (F30%):	0.294
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.966
Plasma Protein Binding (PPB):	95.132%	Volume Distribution (VD):	0.185
Fu:	4.531% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.042
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.216	CYP1A2-substrate:	0.326
CYP2C19-inhibitor:	0.004	CYP2C19-substrate:	0.007
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.19
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.962
CYP3A4-inhibitor:	0.578	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.756 ? 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):

9.321

Half-life (T1/2):

0.782

ADMET: Toxicity

hERG Blockers:	0.117	hERG Blockers (10um):	0.385
Human Hepatotoxicity (H-HT):	0.436	Drug-induced Liver Injury (DILI):	0.277
AMES Toxicity:	0.749	Rat Oral Acute Toxicity:	0.677
Maximum Recommended Daily Dose:	0.936	Skin Sensitization:	0.957
Carcinogencity:	0.748	Eye Corrosion:	0.001
Eye Irritation:	0.147	Respiratory Toxicity:	0.904
Drug-induced Neurotoxicity:	0.532	Ototoxicity:	0.848
Hematotoxicity:	0.23	Drug-induced Nephrotoxicity:	0.765
Genotoxicity:	0.512	RPMI-8226 Immunitoxicity:	0.179
A549 Cytotoxicity:	0.353	Hek293 Cytotoxicity:	0.585
BCF:	2.386 ? 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:	4.631 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.538 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.956 ? 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
NPO21005	Baphia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(92)80059-N]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	DOI[10.1016/S0040-4039(00)86970-1]
NPO4343	Guanomyces polythrix	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[10869195]
NPO17256	Kobresia nepalensis	Species	Cyperaceae	Eukaryota	n.a.	stem	n.a.	PMID[16508191]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17340534]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	stem	n.a.	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	skin-removed stems	Pingle Town, Sichuang Province, China	2008-AUG	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22690646]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[23397723]
NPO20739	Jungermannia hyalina	Species	Jungermanniaceae	Eukaryota	n.a.	Guangxi Zhuang Autonomous Region, China	n.a.	PMID[25856683]
NPO21618	Ircinia oros	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28840725]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31182315]
NPO20212	Callistemon viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31276403]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35430270]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[3760884]
NPO5906	Amaroucium pliciferum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[3840198]
NPO20212	Callistemon viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38893531]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6736970]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6875576]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6875577]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	PMID[6875577]
NPO20671	Selliguea feei	Species	Polypodiaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[8254348]
NPO14136	Acherontia atropus	Species	Sphingidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21550	Achillea macrophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14330	Agave aurea	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20408	Ajuga spectabilis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21426	Alstroemeria revoluta	Species	Alstroemeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21231	Astragalus tragacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21005	Baphia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20212	Callistemon viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20546	Cissus pallidiflorus	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19986	Crataegus davisii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16454	Crinum erubescens	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16044	Cupressus lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15216	Encephalartos altensteinii	Species	Zamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13260	Eria foetida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22510	Eupatorium havanense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11966	Euphorbia kamerunica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19622	Euphorbia marginata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18096	Excoecaria oppositifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20051	Gardenia collinsae	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18620	Grindelia acutifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4343	Guanomyces polythrix	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2854	Gymnosporia senegalensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21618	Ircinia oros	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20739	Jungermannia hyalina	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17256	Kobresia nepalensis	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21365	Ligularia muliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26840	Litsea aciculata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21088	Litsea pulchella	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21486	Marrubium alysson	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20872	Melampodium heterophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20813	Myrmica sabuleti	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3237	Mytilus edulis	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20340	Pausinystalia mayumbensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14466	Penicillium olsonii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16907	Pentzia incana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8650.1	Perilla frutescens var. arguta	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17515	Pronephrium triphyllum	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20671	Selliguea feei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11622.1	Shuteria involucrata var. vestita	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3777	Stevia chamaedrys	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21289	Teucrium oxylepis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19488	Trifolium subterraneum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8678	Trillium camschatcense	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20612	Ursinia abrotanifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19773	Xenorhabdus bovienii	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5906	Amaroucium pliciferum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8650.1	Perilla frutescens var. arguta	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19488	Trifolium subterraneum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19488	Trifolium subterraneum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8650.1	Perilla frutescens var. arguta	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8678	Trillium camschatcense	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11966	Euphorbia kamerunica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17256	Kobresia nepalensis	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17256	Kobresia nepalensis	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21231	Astragalus tragacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21088	Litsea pulchella	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20813	Myrmica sabuleti	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11622.1	Shuteria involucrata var. vestita	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16907	Pentzia incana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14136	Acherontia atropus	Species	Sphingidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18620	Grindelia acutifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20612	Ursinia abrotanifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19488	Trifolium subterraneum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13260	Eria foetida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21005	Baphia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8678	Trillium camschatcense	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14466	Penicillium olsonii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21486	Marrubium alysson	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19622	Euphorbia marginata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20671	Selliguea feei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21365	Ligularia muliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3777	Stevia chamaedrys	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19986	Crataegus davisii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21618	Ircinia oros	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4343	Guanomyces polythrix	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16454	Crinum erubescens	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16044	Cupressus lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11966	Euphorbia kamerunica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19773	Xenorhabdus bovienii	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21550	Achillea macrophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20340	Pausinystalia mayumbensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21426	Alstroemeria revoluta	Species	Alstroemeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18096	Excoecaria oppositifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26840	Litsea aciculata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2854	Gymnosporia senegalensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17515	Pronephrium triphyllum	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3237	Mytilus edulis	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15216	Encephalartos altensteinii	Species	Zamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14330	Agave aurea	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20739	Jungermannia hyalina	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20872	Melampodium heterophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22510	Eupatorium havanense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20546	Cissus pallidiflorus	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21289	Teucrium oxylepis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8650.1	Perilla frutescens var. arguta	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20051	Gardenia collinsae	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20212	Callistemon viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20408	Ajuga spectabilis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5906	Amaroucium pliciferum	Species	n.a.	n.a.	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

Activity Type	# Activity
IC50	1
ED50	2

Activity Type	# Activity
Individual protein	1
Cell line	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	7200.0	nM	PMID[7561895]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell line	P388	Mus musculus	ED50	=	12.5	ug ml-1	PMID[3840198]
NPT137	Cell line	L1210	Mus musculus	ED50	=	25.0	ug ml-1	PMID[3840198]

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 NPC128828 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	24421
0.1-0.2	25247
0.2-0.3	175
0.3-0.4	9
0.4-0.5	3
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
0.6111	Remote Similarity	NPC78159
0.5443	Remote Similarity	NPC102843

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC128828 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7686
0.1-0.2	1442
0.2-0.3	20
0.3-0.4	2
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