NPASS Compound

Natural Product: NPC569519

Natural Product ID	NPC569519
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3~{S},5~{S},8~{S},9~{S},10~{S},13~{R},14~{S},17~{R})-17-[(1~{R},4~{R})-4-ethyl-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1~{H}-cyclopenta[a]phenanthren-3-ol
IUPAC Name	(3~{S},5~{S},8~{S},9~{S},10~{S},13~{R},14~{S},17~{R})-17-[(1~{R},4~{R})-4-ethyl-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1~{H}-cyclopenta[a]phenanthren-3-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 82 85 0 0 0 0 0 0 0 0999 V2000 6.1815 0.1208 -2.1390 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0249 1.1020 -0.9916 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9260 0.3041 0.2882 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7641 -0.6454 0.3216 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4268 -0.0012 0.1825 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2943 -1.0520 0.2088 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3765 -1.7541 1.5006 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0717 -0.3579 -0.1570 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2254 0.2274 -1.5571 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1805 0.1907 -2.1742 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0010 0.0401 -0.9618 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4353 -0.1142 -1.0480 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0135 -1.4051 -1.4854 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5257 -1.3803 -1.4155 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0354 -0.0932 -0.8226 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5148 -0.2049 -0.5725 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0436 1.1368 -0.2029 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3480 0.9424 0.3088 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2690 1.8761 0.8252 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8005 1.6879 0.7843 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3836 0.2371 0.5034 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9764 -0.5805 1.6322 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9108 0.1200 0.4010 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2745 -0.8569 1.3244 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9033 -1.2679 1.1052 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2379 -1.0561 -0.2130 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0888 -2.3004 -1.0149 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1398 1.1126 1.5224 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5560 1.7188 1.4692 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2164 2.3150 1.6369 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2486 0.0519 -2.7540 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0158 0.4234 -2.8211 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4147 -0.9008 -1.7989 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1246 1.6987 -1.2041 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9380 1.6960 -0.9452 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8411 -0.3871 0.2372 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9654 -1.4271 -0.4376 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8481 -1.1742 1.3139 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3346 0.6289 -0.7208 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2817 0.6736 1.0561 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6211 -1.7704 -0.5951 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4885 -1.0540 2.3534 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5363 -2.4255 1.7398 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2728 -2.4462 1.4761 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9150 0.5469 0.4995 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6051 1.2707 -1.5316 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8386 -0.4673 -2.1472 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3572 1.2058 -2.6058 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2816 -0.5303 -2.9678 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7821 0.9726 -0.3508 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8542 0.6997 -1.6715 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7780 -1.5424 -2.5808 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6836 -2.2277 -0.8550 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9331 -2.2041 -0.7699 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0181 -1.5050 -2.3946 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8881 0.7206 -1.5513 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7919 -0.9694 0.1664 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0004 -0.5133 -1.5240 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1955 1.7124 -1.1471 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3179 0.8589 1.2982 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7199 1.7013 1.8466 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4626 2.9774 0.6502 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3560 2.0447 1.7324 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3867 2.2790 -0.0698 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0114 -0.2086 1.8818 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0758 -1.6436 1.4013 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3895 -0.3581 2.5457 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4636 1.1303 0.6464 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3700 -0.4254 2.3680 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9844 -1.7394 1.3656 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2141 -0.8016 1.8736 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8216 -2.3711 1.3196 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5869 -2.2903 -2.0033 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5288 -3.2061 -0.4967 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9491 -2.6184 -1.2315 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1124 0.4742 2.4136 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8172 1.9921 2.5260 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2504 0.8966 1.1880 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5980 2.5642 0.7789 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5131 2.1289 2.4660 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6946 2.5487 0.7077 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7674 3.2482 1.9182 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 6 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 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 3 28 1 0 28 29 1 0 28 30 1 0 26 8 1 0 26 11 1 0 23 12 1 0 21 15 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 0 2 35 1 0 3 36 1 6 4 37 1 0 4 38 1 0 5 39 1 0 5 40 1 0 6 41 1 6 7 42 1 0 7 43 1 0 7 44 1 0 8 45 1 1 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 11 50 1 1 12 51 1 6 13 52 1 0 13 53 1 0 14 54 1 0 14 55 1 0 15 56 1 6 16 57 1 0 16 58 1 0 17 59 1 6 18 60 1 0 19 61 1 0 19 62 1 0 20 63 1 0 20 64 1 0 22 65 1 0 22 66 1 0 22 67 1 0 23 68 1 1 24 69 1 0 24 70 1 0 25 71 1 0 25 72 1 0 27 73 1 0 27 74 1 0 27 75 1 0 28 76 1 0 29 77 1 0 29 78 1 0 29 79 1 0 30 80 1 0 30 81 1 0 30 82 1 0 M END

Standard InCHIKey	LGJMUZUPVCAVPU-JFBKYFIKSA-N
Standard InCHI	InChI=1S/C29H52O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h19-27,30H,7-18H2,1-6H3/t20-,21-,22+,23+,24-,25-,26+,27+,28+,29-/m1/s1
SMILES	CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	416.4	Volume:	484.704 ? Van der Waals volume.
Dense:	0.859	LogP:	9.134 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.818 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-8.589 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	20.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.463	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.371	Fsp³:	1.0
MCE-18:	69.828 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.741	Fluc inhibitor:	0.009 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.765	Promiscuous compounds:	0.1

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.129	MDCK Permeability:	-5.01
Pgp-inhibitor:	0.001	Pgp-substrate:	0.047
PAMPA:	0.113 ? 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%):	0.016	30% Bioavailability (F30%):	0.19
50% Bioavailability (F50%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01	MRP1:	0.027
Plasma Protein Binding (PPB):	92.393%	Volume Distribution (VD):	-0.211
Fu:	9.593% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.08
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.86
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.134
CYP2D6-inhibitor:	0.168	CYP2D6-substrate:	0.384
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.993 ? 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):

19.699

Half-life (T1/2):

1.253

ADMET: Toxicity

hERG Blockers:	0.18	hERG Blockers (10um):	0.306
Human Hepatotoxicity (H-HT):	0.681	Drug-induced Liver Injury (DILI):	0.328
AMES Toxicity:	0.112	Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.481	Skin Sensitization:	0.998
Carcinogencity:	0.917	Eye Corrosion:	0.988
Eye Irritation:	0.999	Respiratory Toxicity:	0.977
Drug-induced Neurotoxicity:	0.027	Ototoxicity:	0.443
Hematotoxicity:	0.534	Drug-induced Nephrotoxicity:	0.768
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.026
A549 Cytotoxicity:	0.665	Hek293 Cytotoxicity:	0.644
BCF:	3.564 ? 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:	5.142 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.284 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.991 ? 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
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF00714468]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(00)97029-8]
NPO15810	Zea mays	Species	Poaceae	Eukaryota		n.a.	n.a.	DOI[10.1021/jf00055a023]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[11539687]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713418]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730237]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[17190444]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18603435]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[20469887]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21080643]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	husk	n.a.	PMID[21574561]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21574561]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[23292602]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327299]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29762032]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	pollen	n.a.	PMID[8987503]
NPO49614	Chattonella marina	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO54737	Piper nigrum L.	Genus	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO56164	Pteleopsis hylodendron	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO320	Coffea canephora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO61037	Coffea congensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO45618	Fagara tessmannii Engl.	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO42498	Hordeum vulgare L.cv Mammut	Genus	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO53485	Cyathea podophylla	Species	Cyatheaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11583	Calycanthus floridus	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO61949	Coffea stenophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO53726	Coffea sessiliflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO47654	Coffea salvatrix	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO44221	Coffea racemosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18807	Coffea pseudozanguebariae	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO59704	Coffea liberica var.liberica	Genus	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO57576	Coffea liberica var.dewevrei	Genus	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO62336	Coffea kapakata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO61267	Coffea humilis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO61625	Coffea humblotiana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO53050	Coffea hetero calyx	Genus	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO62559	Coffea eugenioides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO45673	Coffea charrieriana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Cob	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Silk Stigma Style	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Silk Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO320	Coffea canephora	Species	Rubiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Husk Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Pollen Or Spore	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11583	Calycanthus floridus	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11583	Calycanthus floridus	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO320	Coffea canephora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11583	Calycanthus floridus	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11583	Calycanthus floridus	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18807	Coffea pseudozanguebariae	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO223	Rhaponticum carthamoides	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]
NPO320	Coffea canephora	Species	Rubiaceae	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 NPC569519 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	27021
0.1-0.2	20731
0.2-0.3	1762
0.3-0.4	245
0.4-0.5	70
0.5-0.6	19
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC148174
0.7556	Intermediate Similarity	NPC71460
0.7556	Intermediate Similarity	NPC218585
0.6667	Remote Similarity	NPC114891
0.6346	Remote Similarity	NPC167702
0.6346	Remote Similarity	NPC280026
0.625	Remote Similarity	NPC320549
0.625	Remote Similarity	NPC156277
0.625	Remote Similarity	NPC58057
0.625	Remote Similarity	NPC151018
0.62	Remote Similarity	NPC254340
0.5965	Remote Similarity	NPC323180
0.5833	Remote Similarity	NPC281540
0.5833	Remote Similarity	NPC159654
0.5833	Remote Similarity	NPC167995
0.5833	Remote Similarity	NPC118937
0.5741	Remote Similarity	NPC10476
0.5741	Remote Similarity	NPC192456
0.5667	Remote Similarity	NPC320478
0.5636	Remote Similarity	NPC257347
0.5385	Remote Similarity	NPC327728
0.5385	Remote Similarity	NPC6120
0.5385	Remote Similarity	NPC131892
0.5385	Remote Similarity	NPC213178
0.5385	Remote Similarity	NPC103822
0.5357	Remote Similarity	NPC230301
0.5263	Remote Similarity	NPC477817
0.5179	Remote Similarity	NPC247325
0.5088	Remote Similarity	NPC470360
0.5088	Remote Similarity	NPC603222

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC569519 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7857
0.1-0.2	1173
0.2-0.3	82
0.3-0.4	23
0.4-0.5	7
0.5-0.6	4
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6346	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4808	Phase 2
0.625	Remote Similarity	NPD4809	Phase 4
0.5385	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5385	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5357	Remote Similarity	NPD7339	Approved
0.5283	Remote Similarity	NPD4787	Phase 1

Bioactivity similarity

Similar Natural Products in NPASS

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data