NPASS Compound

Natural Product: NPC107421

Natural Product ID	NPC107421
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LNPHICKKKGHENP-HPEILCDZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	46703589
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 88 91 0 0 0 0 0 0 0 0999 V2000 8.3576 2.8432 0.8240 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3864 1.7020 -0.1654 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0473 2.2214 -1.4261 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9974 1.2493 -0.4192 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6708 -0.0067 -0.7044 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2694 -0.4353 -0.9550 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8517 -1.5027 0.0664 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7864 -2.6600 -0.0990 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4004 -1.8688 -0.1130 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1141 -2.5773 -1.3830 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1873 -1.6534 -2.1175 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7440 -0.7012 -1.0615 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8511 0.7149 -1.6454 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2987 -0.8789 -0.6625 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0534 -2.2047 0.0160 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4393 -2.3750 0.2016 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1281 -1.0431 0.0211 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3453 0.0797 0.6592 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3482 -0.1931 2.1691 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0942 1.3578 0.4174 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3506 1.2010 -0.3619 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1273 -0.0347 -0.0823 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4498 0.2572 0.6488 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0226 0.7246 2.0445 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1655 -1.0509 0.7440 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6564 -0.9370 0.8021 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2216 0.1441 -0.0522 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4126 1.4037 0.1710 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7378 1.9774 1.5236 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9242 2.4150 -0.8669 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0834 1.2244 -0.0684 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0284 0.5128 0.5623 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.4041 -1.0208 0.5842 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0282 0.1287 0.2220 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6118 -0.7615 -0.0043 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0746 -0.9341 1.3189 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1904 0.6999 0.3610 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1687 2.7793 1.5788 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4476 3.8222 0.3109 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3978 2.8707 1.4022 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0097 2.7040 -1.1046 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3423 1.3912 -2.1017 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4555 3.0076 -1.9228 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2005 1.9775 -0.3710 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5046 -0.7166 -0.7447 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2011 -0.8154 -1.9889 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6275 0.4763 -0.8345 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7381 -2.4013 0.4173 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0836 -2.8142 -1.1763 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4262 -3.5992 0.3605 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1462 -2.5508 0.7390 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9950 -2.7660 -2.0175 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6549 -3.5901 -1.2027 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3566 -2.1829 -2.6221 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7455 -1.1281 -2.9327 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9269 0.9394 -2.2215 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7069 0.7144 -2.3454 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0090 1.4287 -0.8119 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3071 -0.7553 -1.5720 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5472 -2.2223 0.9889 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3928 -3.0660 -0.5971 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6820 -2.8247 1.1970 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8774 -3.0653 -0.5505 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2829 -0.8429 -1.0749 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9502 -1.0612 2.4344 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7983 0.6807 2.7216 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3303 -0.3145 2.5613 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4060 2.0137 -0.1933 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2282 1.9153 1.3725 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0231 2.0765 -0.1473 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1264 1.3005 -1.4641 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4451 -0.4830 -1.0587 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8340 0.6130 2.7810 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5933 1.7284 1.9766 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2363 -0.0237 2.3579 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8393 -1.5373 1.7087 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8823 -1.7758 -0.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0090 -0.8532 1.8471 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0836 -1.9142 0.4301 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2766 -0.0976 -1.1195 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6306 2.6558 1.4334 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0998 1.1529 2.2053 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9423 2.5786 1.9646 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8514 2.9084 -0.5174 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0934 3.1388 -1.0313 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0492 1.8668 -1.8197 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1705 -1.6321 2.0209 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6982 0.2752 -0.3863 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 2 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 1 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 28 31 1 0 27 32 1 0 22 33 1 0 18 34 1 0 12 35 1 0 7 36 1 1 2 37 1 0 35 9 1 0 34 14 1 0 33 17 1 0 31 23 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 3 42 1 0 3 43 1 0 4 44 1 0 5 45 1 0 6 46 1 0 6 47 1 0 8 48 1 0 8 49 1 0 8 50 1 0 9 51 1 1 10 52 1 0 10 53 1 0 11 54 1 0 11 55 1 0 13 56 1 0 13 57 1 0 13 58 1 0 14 59 1 6 15 60 1 0 15 61 1 0 16 62 1 0 16 63 1 0 17 64 1 6 19 65 1 0 19 66 1 0 19 67 1 0 20 68 1 0 20 69 1 0 21 70 1 0 21 71 1 0 22 72 1 6 24 73 1 0 24 74 1 0 24 75 1 0 25 76 1 0 25 77 1 0 26 78 1 0 26 79 1 0 27 80 1 6 29 81 1 0 29 82 1 0 29 83 1 0 30 84 1 0 30 85 1 0 30 86 1 0 36 87 1 0 37 88 1 0 M END

Standard InCHIKey	LNPHICKKKGHENP-HPEILCDZSA-N
Standard InCHI	InChI=1S/C30H51BrO6/c1-25(2,32)15-9-16-27(5,33)21-13-18-29(7,35-21)24-11-10-22-28(6,36-24)19-14-23(34-22)30(8)17-12-20(31)26(3,4)37-30/h9,15,20-24,32-33H,10-14,16-19H2,1-8H3/b15-9+/t20-,21+,22-,23-,24-,27-,28+,29+,30+/m1/s1
SMILES	CC(C)(/C=C/C[C@](C)([C@@H]1CC[C@@](C)([C@H]2CC[C@@H]3[C@](C)(CC[C@H]([C@]4(C)CC[C@H](C(C)(C)O4)Br)O3)O2)O1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	586.29	Volume:	562.599 ? Van der Waals volume.
Dense:	1.042	LogP:	3.03 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.292 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.011 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	23.0
TPSA:	77.38 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.294	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.444	Fsp³:	0.933
MCE-18:	90.517 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.358	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:	0.036 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.661	Promiscuous compounds:	0.423

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.726	MDCK Permeability:	-4.804
Pgp-inhibitor:	0.906	Pgp-substrate:	0.0
PAMPA:	0.181 ? 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%):	0.025	30% Bioavailability (F30%):	0.014
50% Bioavailability (F50%):	0.855

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.019
Plasma Protein Binding (PPB):	78.924%	Volume Distribution (VD):	0.011
Fu:	15.351% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.776
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.904	CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.753	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.825	CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.916
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.106
HLM stability:	0.956 ? 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):

9.992

Half-life (T1/2):

1.186

ADMET: Toxicity

hERG Blockers:	0.137	hERG Blockers (10um):	0.499
Human Hepatotoxicity (H-HT):	0.413	Drug-induced Liver Injury (DILI):	0.211
AMES Toxicity:	0.663	Rat Oral Acute Toxicity:	0.782
Maximum Recommended Daily Dose:	0.913	Skin Sensitization:	0.996
Carcinogencity:	0.921	Eye Corrosion:	0.012
Eye Irritation:	0.266	Respiratory Toxicity:	0.963
Drug-induced Neurotoxicity:	0.404	Ototoxicity:	0.536
Hematotoxicity:	0.108	Drug-induced Nephrotoxicity:	0.141
Genotoxicity:	0.738	RPMI-8226 Immunitoxicity:	0.128
A549 Cytotoxicity:	0.154	Hek293 Cytotoxicity:	0.681
BCF:	1.574 ? 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:	3.597 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.118 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.336 ? 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
NPO28122	Senecio chionophilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387646]
NPO28539	Xestospongia vanilla	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21945	Amomum melegueta	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27889	Anacyclus monanthos	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28505	Arum palaestinum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28331	Astragalus siculus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28645	Chondria armata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28403	Comanthus bennetti	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28105	Coriolopsis gallica	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28082	Corydalis tashiroi	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27969	Elvira biflora	Species	Trochilidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28493	Euphorbia cuneata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28522	Flustra denticulata	Species	Flustridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28420	Guizotia scabra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28314	Hakea trifurcata	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12214	Leontice robustum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28279	Mikania cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28156	Nezara viridula	Species	Pentatomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27701	Otholobium glandulosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28030	Polysiphonia nigra	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28227	Prunus speciosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27849	Raoulia australis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28122	Senecio chionophilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27768	Terminalia brachystemma	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27917	Ulmus campestris	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12214	Leontice robustum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28645	Chondria armata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28645	Chondria armata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12214	Leontice robustum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12214	Leontice robustum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28331	Astragalus siculus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28522	Flustra denticulata	Species	Flustridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28493	Euphorbia cuneata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21945	Amomum melegueta	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28314	Hakea trifurcata	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28645	Chondria armata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27917	Ulmus campestris	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12214	Leontice robustum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28030	Polysiphonia nigra	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27889	Anacyclus monanthos	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28403	Comanthus bennetti	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28420	Guizotia scabra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27969	Elvira biflora	Species	Trochilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28156	Nezara viridula	Species	Pentatomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28122	Senecio chionophilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28082	Corydalis tashiroi	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28105	Coriolopsis gallica	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27701	Otholobium glandulosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28539	Xestospongia vanilla	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27768	Terminalia brachystemma	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27849	Raoulia australis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28505	Arum palaestinum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28279	Mikania cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28227	Prunus speciosa	Species	Rosaceae	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 NPC107421 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	30783
0.1-0.2	18774
0.2-0.3	267
0.3-0.4	12
0.4-0.5	8
0.5-0.6	11
0.6-0.7	4
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
0.619	Remote Similarity	NPC253123
0.6034	Remote Similarity	NPC181838
0.6034	Remote Similarity	NPC137345
0.6032	Remote Similarity	NPC605828
0.5692	Remote Similarity	NPC470173
0.5606	Remote Similarity	NPC606704
0.5441	Remote Similarity	NPC5361
0.5441	Remote Similarity	NPC607487
0.5441	Remote Similarity	NPC609102
0.5352	Remote Similarity	NPC244002
0.5294	Remote Similarity	NPC602272
0.5294	Remote Similarity	NPC602759
0.5286	Remote Similarity	NPC470176
0.5278	Remote Similarity	NPC470175
0.5135	Remote Similarity	NPC470174

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC107421 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7854
0.1-0.2	1296
0.2-0.3	0
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data