NPASS Compound

Natural Product: NPC89325

Natural Product ID	NPC89325
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KARYILHRSIVKPA-XDJFTHQSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101243911
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

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 115122 0 0 0 0 0 0 0 0999 V2000 10.4913 -0.4652 1.7223 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7784 0.8449 1.8082 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4632 0.8081 2.5103 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4350 1.5206 1.6601 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3032 0.8493 0.2929 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3211 1.6056 -0.5808 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9920 2.3780 -1.6734 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5205 0.4829 -1.2539 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6323 -0.5857 -0.1618 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3247 -0.3087 0.6062 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4214 -0.2469 -0.5461 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0169 0.1503 -0.4083 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2587 -0.5706 0.6794 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0393 0.2062 0.8287 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6918 0.5278 -0.4661 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1648 0.1767 -0.3468 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3583 -1.2967 -0.1459 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4609 -2.1316 -1.0191 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7691 -1.3957 -2.0927 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1092 -0.0923 -1.6927 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4734 0.8671 -2.8539 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3671 -0.2096 -1.7297 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0346 0.4755 -2.8959 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5077 0.5133 -2.7735 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2348 0.3209 -3.7060 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0892 0.8009 -1.4394 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7038 2.2053 -1.0719 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6813 -1.7197 -0.2284 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1871 -2.2139 0.9253 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4873 -1.5483 1.2741 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1064 -2.2287 2.4315 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4371 -3.4628 2.9405 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6483 -4.2253 1.9290 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2098 -5.5997 1.6540 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3663 -6.3189 2.8609 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5110 -3.5639 0.7149 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3563 -4.3496 3.5147 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4135 -2.6245 2.0582 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3133 -0.1913 1.4005 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9323 0.5808 0.4630 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0095 1.3778 1.2210 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8321 2.0727 0.1936 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2150 2.1776 -1.1514 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7268 2.1690 -1.1800 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1935 3.6006 -1.2956 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8131 4.2631 -2.3616 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1213 1.5130 -0.1303 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7131 1.1922 -2.0380 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2403 3.2931 0.7309 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7506 0.5059 2.0189 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7605 -0.4035 0.5387 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5649 0.8025 -0.2660 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5456 1.4648 0.4287 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1721 -0.9907 0.8042 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5892 -0.2772 1.7331 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1979 -1.0824 2.5975 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4461 1.5334 2.4074 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4786 1.3365 3.4950 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1449 -0.2418 2.6741 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4606 1.3772 2.2229 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5899 2.5954 1.6041 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7054 2.2109 0.0984 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9313 3.4868 -1.5047 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0427 2.0375 -1.8441 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4936 2.2164 -2.6695 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0566 0.1676 -2.1605 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4732 -1.5796 -0.6275 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1236 -1.1432 1.3145 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3481 0.6716 1.1188 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4811 -1.2161 -1.1056 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9068 1.2182 -0.2473 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8672 -0.4254 1.6186 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1160 -1.6350 0.5092 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3001 1.1907 1.2849 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6928 -0.2167 1.6144 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6955 1.6509 -0.6392 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6839 0.5870 -1.2139 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 0.7470 0.5402 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0619 -1.5103 0.9044 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1303 -2.8911 -1.5224 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7418 -2.7655 -0.4540 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4763 -1.2898 -2.9491 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0386 -2.0655 -2.4929 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1118 0.4861 -3.8193 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5997 0.7938 -2.9285 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2385 1.9023 -2.6166 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6165 -1.3077 -1.8672 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8188 -0.1603 -3.8031 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6963 1.4966 -3.0860 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7609 2.4986 -1.6175 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6207 2.4036 -0.0065 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4874 2.8747 -1.5332 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5212 -2.1862 1.7984 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1389 -1.6728 0.3527 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2754 -1.4684 3.2337 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7688 -3.1472 3.7776 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6022 -4.3909 2.3026 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5097 -6.1598 0.9888 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2054 -5.5791 1.1905 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7355 -6.0223 3.5613 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0274 -4.6505 2.8391 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3743 -3.3023 1.3209 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4988 0.0403 -0.3083 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5107 2.0807 1.9192 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7846 1.4708 0.0948 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5549 3.1541 -1.6045 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4009 1.6682 -2.1189 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4363 4.1659 -0.3801 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1086 3.6215 -1.4889 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6161 3.7336 -3.1827 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4183 1.4413 -2.9534 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5285 3.6062 1.3471 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2280 0.9536 2.7417 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3489 2.5427 0.6130 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4716 1.4231 -0.1869 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 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 1 1 17 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 32 37 1 0 31 38 1 0 30 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 44 47 1 0 43 48 1 0 42 49 1 0 41 50 1 0 9 51 1 0 5 52 1 6 52 53 1 0 53 2 1 0 51 5 1 0 26 8 1 0 36 29 1 0 47 40 1 0 26 11 1 0 22 12 1 0 20 15 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 1 3 58 1 0 3 59 1 0 4 60 1 0 4 61 1 0 6 62 1 1 7 63 1 0 7 64 1 0 7 65 1 0 8 66 1 6 9 67 1 6 10 68 1 0 10 69 1 0 11 70 1 6 12 71 1 1 13 72 1 0 13 73 1 0 14 74 1 0 14 75 1 0 15 76 1 6 16 77 1 0 16 78 1 0 17 79 1 1 18 80 1 0 18 81 1 0 19 82 1 0 19 83 1 0 21 84 1 0 21 85 1 0 21 86 1 0 22 87 1 6 23 88 1 0 23 89 1 0 27 90 1 0 27 91 1 0 27 92 1 0 29 93 1 1 30 94 1 6 31 95 1 1 32 96 1 1 33 97 1 1 34 98 1 0 34 99 1 0 35100 1 0 37101 1 0 38102 1 0 40103 1 6 41104 1 1 42105 1 6 43106 1 6 44107 1 6 45108 1 0 45109 1 0 46110 1 0 48111 1 0 49112 1 0 50113 1 0 53114 1 0 53115 1 0 M END

Standard InCHIKey	KARYILHRSIVKPA-XDJFTHQSSA-N
Standard InCHI	InChI=1S/C39H62O14/c1-17-7-10-39(48-16-17)18(2)28-24(53-39)12-23-21-6-5-19-11-20(8-9-37(19,3)22(21)13-27(42)38(23,28)4)49-36-34(32(46)30(44)26(15-41)51-36)52-35-33(47)31(45)29(43)25(14-40)50-35/h17-26,28-36,40-41,43-47H,5-16H2,1-4H3/t17-,18+,19-,20+,21-,22+,23+,24+,25-,26-,28+,29-,30+,31+,32+,33-,34-,35+,36-,37+,38-,39-/m1/s1
SMILES	C[C@@H]1CC[C@@]2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC[C@@H]6C[C@H](CC[C@]6(C)[C@H]5CC(=O)[C@]34C)O[C@H]3[C@@H]([C@H]([C@H]([C@@H](CO)O3)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	754.41	Volume:	735.075 ? Van der Waals volume.
Dense:	1.026	LogP:	1.503 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.268 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.938 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	43.0
TPSA:	214.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	7.0	Rings:	8.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.185	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.317	Fsp³:	0.974
MCE-18:	203.052 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.737	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? 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:	0.187	Promiscuous compounds:	0.173

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.926	MDCK Permeability:	-5.142
Pgp-inhibitor:	0.002	Pgp-substrate:	0.174
PAMPA:	0.979 ? 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):	0.136
20% Bioavailability (F20%):	0.407	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.125
Plasma Protein Binding (PPB):	56.351%	Volume Distribution (VD):	-0.422
Fu:	41.234% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.205
BSEP inhibitor:	0.419

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.245	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.197	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.938
HLM stability:	0.12 ? 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):

1.295

Half-life (T1/2):

2.382

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.078
Human Hepatotoxicity (H-HT):	0.735	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.957	Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.042	Skin Sensitization:	1.0
Carcinogencity:	0.331	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.01
Drug-induced Neurotoxicity:	0.012	Ototoxicity:	0.994
Hematotoxicity:	0.434	Drug-induced Nephrotoxicity:	0.82
Genotoxicity:	0.031	RPMI-8226 Immunitoxicity:	0.298
A549 Cytotoxicity:	0.973	Hek293 Cytotoxicity:	0.926
BCF:	1.167 ? 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:	3.273 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.465 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.775 ? 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
NPO19920	Yucca gloriosa	Species	Asparagaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/0031-9422(89)80212-2]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[11045899]
NPO21106	Isatis costata	Species	Brassicaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17846565]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[19555186]
NPO19108	Arthrinium sacchari	Species	Apiosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718054]
NPO22631	Actinopolyspora erythraea	Species	Actinopolysporaceae	Bacteria	n.a.	mycelium	n.a.	PMID[21870828]
NPO21735	Clausena anisum-olens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28368606]
NPO21635	Pandalus borealis	Species	Pandalidae	Eukaryota	n.a.	n.a.	n.a.	PMID[3349210]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	Latex	n.a.	n.a.	PMID[6481361]
NPO20358	Streptomyces maritimus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20032	Prunus sibirica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21106	Isatis costata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22631	Actinopolyspora erythraea	Species	Actinopolysporaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22938	Genista hystrix	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19380	Styela plicata	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22578	Speranskia tuberculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19108	Arthrinium sacchari	Species	Apiosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23056	Isaria japonica	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20677	Fraxinus angustifolia	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18197	Cadlina luteomarginata	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7217	Plakobranchus ocellatus	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14364	Alisma plantago-aquatica	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20182	Euonymus pendulus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22246	Aplidium longithorax	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20042	Ambrosia cumanensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25227	Senecio roseus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22578	Speranskia tuberculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20952	Dioscorea cirrhosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19070	Cassia dentata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20952	Dioscorea cirrhosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19070	Cassia dentata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22578	Speranskia tuberculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19070	Cassia dentata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20032	Prunus sibirica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21635	Pandalus borealis	Species	Pandalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21874	Cercospora melonis	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5927	Cortinarius venetus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14364	Alisma plantago-aquatica	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15934	Rhododendron ponticum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22453	Befaria racemosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12005	Amomum zambesiacum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22631	Actinopolyspora erythraea	Species	Actinopolysporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14211	Acinetobacter junii	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21106	Isatis costata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17898	Buckiella undulata	Species	Hypnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22697	Licaria mahuba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22119	Echinops bannaticus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20358	Streptomyces maritimus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22321	Euphorbia lamprocarpa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19108	Arthrinium sacchari	Species	Apiosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18197	Cadlina luteomarginata	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23094	Pectinophora gossypiella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22938	Genista hystrix	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22993	Veronica hederifolia	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22187	Ostrea virginica	Species	Ostreidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23133	Gypsophila patrini	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23056	Isaria japonica	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19693	Lobaria oregana	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21246	Helichrysum anomalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19380	Styela plicata	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27833	Xerotus discolor	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7217	Plakobranchus ocellatus	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9972	Angostura granulosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20032	Prunus sibirica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21997	Benzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20952	Dioscorea cirrhosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22246	Aplidium longithorax	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20677	Fraxinus angustifolia	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19070	Cassia dentata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17092	Viguiera dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20506	Batatas edulis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25227	Senecio roseus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22881	Cryptotermes brevis	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19920	Yucca gloriosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23176	Schefflera bodinieri	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22578	Speranskia tuberculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17819	Ferula transiliensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23475	Psoralea acaulis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20042	Ambrosia cumanensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21735	Clausena anisum-olens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18568	Artemisia aucheri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20182	Euonymus pendulus	Species	Celastraceae	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 NPC89325 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	25211
0.1-0.2	21409
0.2-0.3	2609
0.3-0.4	448
0.4-0.5	91
0.5-0.6	51
0.6-0.7	23
0.7-0.8	0
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8989	High Similarity	NPC92890
0.8235	Intermediate Similarity	NPC297348
0.8235	Intermediate Similarity	NPC249204
0.8235	Intermediate Similarity	NPC48339
0.8235	Intermediate Similarity	NPC141769
0.8235	Intermediate Similarity	NPC477547
0.7841	Intermediate Similarity	NPC477451
0.7653	Intermediate Similarity	NPC475319
0.7419	Intermediate Similarity	NPC107962
0.7391	Intermediate Similarity	NPC211354
0.7234	Intermediate Similarity	NPC215408
0.7048	Intermediate Similarity	NPC233433
0.6804	Remote Similarity	NPC6295
0.6774	Remote Similarity	NPC294686
0.6757	Remote Similarity	NPC220836
0.6737	Remote Similarity	NPC206003
0.6737	Remote Similarity	NPC473610
0.6698	Remote Similarity	NPC108072
0.6667	Remote Similarity	NPC160426
0.6596	Remote Similarity	NPC234352
0.6535	Remote Similarity	NPC202898
0.6495	Remote Similarity	NPC19400
0.6489	Remote Similarity	NPC325828
0.6486	Remote Similarity	NPC94086
0.6486	Remote Similarity	NPC473817
0.6458	Remote Similarity	NPC474399
0.6458	Remote Similarity	NPC222731
0.6337	Remote Similarity	NPC113044
0.6337	Remote Similarity	NPC283829
0.6337	Remote Similarity	NPC161676
0.6286	Remote Similarity	NPC128572
0.6275	Remote Similarity	NPC475351
0.6204	Remote Similarity	NPC475625
0.6162	Remote Similarity	NPC107188
0.6	Remote Similarity	NPC475643
0.5943	Remote Similarity	NPC477809
0.5926	Remote Similarity	NPC184617
0.5922	Remote Similarity	NPC141433
0.5918	Remote Similarity	NPC291203
0.5918	Remote Similarity	NPC217205
0.5909	Remote Similarity	NPC161035
0.5909	Remote Similarity	NPC170438
0.5842	Remote Similarity	NPC54619
0.5825	Remote Similarity	NPC125324
0.5816	Remote Similarity	NPC177834
0.578	Remote Similarity	NPC97700
0.578	Remote Similarity	NPC30856
0.5773	Remote Similarity	NPC485594
0.5741	Remote Similarity	NPC471464
0.5673	Remote Similarity	NPC485595
0.5644	Remote Similarity	NPC250393
0.5619	Remote Similarity	NPC195297
0.5588	Remote Similarity	NPC128123
0.5565	Remote Similarity	NPC132080
0.5556	Remote Similarity	NPC181845
0.5545	Remote Similarity	NPC480555
0.5545	Remote Similarity	NPC150372
0.5455	Remote Similarity	NPC249553
0.5455	Remote Similarity	NPC51172
0.5455	Remote Similarity	NPC49032
0.5455	Remote Similarity	NPC182900
0.5408	Remote Similarity	NPC24960
0.5323	Remote Similarity	NPC305771
0.5323	Remote Similarity	NPC94072
0.5323	Remote Similarity	NPC169816
0.5315	Remote Similarity	NPC300557
0.5304	Remote Similarity	NPC232037
0.5299	Remote Similarity	NPC92297
0.5299	Remote Similarity	NPC480553
0.5273	Remote Similarity	NPC470433
0.5273	Remote Similarity	NPC46190
0.5273	Remote Similarity	NPC171073
0.5259	Remote Similarity	NPC470864
0.5217	Remote Similarity	NPC13193
0.5217	Remote Similarity	NPC116756
0.5182	Remote Similarity	NPC473601
0.5138	Remote Similarity	NPC305423
0.5135	Remote Similarity	NPC602423
0.5128	Remote Similarity	NPC480554
0.5122	Remote Similarity	NPC273002
0.5102	Remote Similarity	NPC277715
0.5096	Remote Similarity	NPC210157
0.5094	Remote Similarity	NPC306131
0.5094	Remote Similarity	NPC200802
0.5081	Remote Similarity	NPC15918
0.5041	Remote Similarity	NPC470866

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC89325 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7475
0.1-0.2	1604
0.2-0.3	61
0.3-0.4	6
0.4-0.5	2
0.5-0.6	0
0.6-0.7	2
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
0.6489	Remote Similarity	NPD8171	Phase 2
0.6139	Remote Similarity	NPD8170	Phase 2

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