NPASS Compound

Natural Product: NPC478064

Natural Product ID	NPC478064
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	butyl (2S,3S,4S,5R,6R)-6-[[(3S,6aR,6bS,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-10-[(2E)-3,7-dimethylocta-2,6-dienoyl]oxy-7,8-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-(2-methylbutanoyloxy)-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylate
IUPAC Name	butyl (2S,3S,4S,5R,6R)-6-[[(3S,6aR,6bS,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-10-[(2E)-3,7-dimethylocta-2,6-dienoyl]oxy-7,8-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-(2-methylbutanoyloxy)-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44575723
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene 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 195202 0 0 0 0 0 0 0 0999 V2000 -5.3435 -4.7617 3.7217 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4661 -3.7572 3.7403 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4715 -2.9632 5.0430 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6234 -1.9463 5.0163 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3797 -1.1204 3.9265 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1387 -0.0491 3.5060 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1683 0.2354 4.1624 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7303 0.7536 2.2828 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.8686 0.6380 1.2402 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5685 -0.6501 0.5084 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3285 -0.4732 -0.3762 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3231 0.2625 0.4478 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5939 0.1955 1.8310 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0124 -0.2486 0.4118 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0698 0.6753 0.0671 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3733 1.2415 1.3141 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8998 1.4546 1.0759 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2390 0.0606 0.9085 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1669 0.3743 0.4875 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8276 1.2000 1.5522 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2552 0.8962 1.7241 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0003 0.1325 0.9288 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4309 -0.0267 1.3153 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1936 1.1439 0.8122 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6355 1.0289 1.2569 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1805 -0.1350 0.5255 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4266 -1.4361 0.6565 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0199 -1.3766 1.0999 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1287 -2.2219 0.2800 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2428 -1.5817 -0.7298 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3650 -0.4714 -0.2580 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9433 -0.8059 -0.0003 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1900 -1.1911 -1.2890 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2148 -1.5586 -1.0195 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0258 -0.6865 -0.1216 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0784 0.0984 -0.8695 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5973 1.0531 -1.9032 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8362 -1.0048 -1.6596 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8163 -2.0411 0.8629 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3754 0.5756 -1.3862 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9615 -1.2084 -1.8978 O 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12.6498 4.4220 0.8579 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4248 3.5767 -1.4174 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8590 1.0786 2.7155 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3187 2.2701 0.6523 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3473 -0.5336 2.2989 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6301 0.2863 -1.4848 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5039 -0.2611 -2.7119 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8013 -0.5672 -3.4207 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.2858 0.6683 -4.1382 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2101 1.4597 -4.7887 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9235 1.5012 -4.0495 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5760 0.2760 -3.5658 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8353 2.6414 -3.0621 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5193 2.7396 -2.6274 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9899 1.0366 -6.1094 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9554 1.4556 -3.1873 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6054 -1.6155 -4.3313 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2122 -1.5988 1.4695 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8469 1.7597 0.4509 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0023 2.5135 0.6401 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.6858 3.8661 1.1815 C 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0 0 0 0 0 0 0 0 0 14.4400 3.2809 -1.7571 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9763 1.2287 3.3312 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3441 0.1238 3.0278 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5798 1.8912 3.0254 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7566 3.1590 0.9498 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3451 2.3276 1.0666 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3693 2.0935 -0.4376 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8054 0.1548 3.0495 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3807 -0.8105 2.7599 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0145 -1.4194 2.3100 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0999 -1.3180 -2.4949 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6037 -0.8956 -2.7497 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0216 0.3100 -4.8961 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5883 2.5328 -4.8131 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1173 1.7668 -4.8311 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5018 2.4744 -2.2217 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0940 3.5972 -3.6029 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9448 3.2419 -3.2696 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0218 1.8166 -6.7384 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5072 0.8739 -2.5789 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7041 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50 1 0 50 51 1 0 26 52 1 0 52 53 1 0 53 54 2 0 53 55 1 0 55 56 2 0 56 57 1 0 56 58 1 0 58 59 1 0 59 60 1 0 60 61 2 3 61 62 1 0 61 63 1 0 25 64 1 0 25 65 1 0 18 66 1 1 11 67 1 0 67 68 1 0 68 69 1 0 69 70 1 0 70 71 1 0 71 72 1 0 72 73 1 0 72 74 1 0 74 75 1 0 71 76 1 0 70 77 1 0 69 78 1 0 10 79 1 0 9 80 1 0 80 81 1 0 81 82 1 0 82 83 1 0 83 84 1 0 84 85 1 0 84 86 1 0 86 87 1 0 83 88 1 0 82 89 1 0 13 8 1 0 36 15 1 0 35 18 1 0 32 19 1 0 31 22 1 0 28 23 1 0 73 68 1 0 85 81 1 0 1 90 1 0 1 91 1 0 1 92 1 0 2 93 1 0 2 94 1 0 3 95 1 0 3 96 1 0 4 97 1 0 4 98 1 0 8 99 1 1 9100 1 1 10101 1 6 11102 1 6 12103 1 6 15104 1 6 16105 1 0 16106 1 0 17107 1 0 17108 1 0 19109 1 6 20110 1 0 20111 1 0 21112 1 0 23113 1 1 24114 1 0 24115 1 0 26116 1 6 27117 1 1 29118 1 1 30119 1 6 33120 1 0 33121 1 0 34122 1 0 34123 1 0 35124 1 0 37125 1 0 37126 1 0 37127 1 0 38128 1 0 38129 1 0 38130 1 0 39131 1 0 39132 1 0 39133 1 0 40134 1 0 40135 1 0 40136 1 0 41137 1 0 42138 1 0 43139 1 0 43140 1 0 44141 1 0 48142 1 0 49143 1 0 49144 1 0 49145 1 0 50146 1 0 50147 1 0 51148 1 0 51149 1 0 51150 1 0 55151 1 0 57152 1 0 57153 1 0 57154 1 0 58155 1 0 58156 1 0 59157 1 0 59158 1 0 60159 1 0 62160 1 0 62161 1 0 62162 1 0 63163 1 0 63164 1 0 63165 1 0 64166 1 0 64167 1 0 64168 1 0 65169 1 0 65170 1 0 65171 1 0 66172 1 0 66173 1 0 66174 1 0 68175 1 1 69176 1 1 70177 1 6 71178 1 6 72179 1 6 74180 1 0 74181 1 0 75182 1 0 76183 1 0 77184 1 0 78185 1 0 79186 1 0 81187 1 1 82188 1 1 83189 1 1 84190 1 6 86191 1 0 86192 1 0 87193 1 0 88194 1 0 89195 1 0 M END

Standard InCHIKey	NRJDYTBXPQINHA-MPKWBJNVSA-N
Standard InCHI	InChI=1S/C66H106O23/c1-14-16-26-81-57(80)51-49(86-58-46(74)44(72)38(30-68)83-58)48(76)50(87-59-47(75)45(73)43(71)37(29-67)82-59)60(88-51)84-41-23-24-63(11)39(62(41,9)10)22-25-64(12)40(63)21-20-35-36-28-61(7,8)54(85-42(70)27-33(5)19-17-18-32(3)4)55(89-56(79)34(6)15-2)66(36,31-69)53(78)52(77)65(35,64)13/h18,20,27,34,36-41,43-55,58-60,67-69,71-78H,14-17,19,21-26,28-31H2,1-13H3/b33-27+/t34?,36-,37+,38-,39?,40+,41-,43+,44-,45-,46+,47+,48-,49-,50+,51-,52-,53+,54-,55-,58-,59-,60+,63-,64+,65-,66-/m0/s1
SMILES	CCCCOC(=O)[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC=C5[C@@H]6CC([C@H]([C@@H]([C@@]6([C@@H]([C@@H]([C@]5([C@@]4(CCC3C2(C)C)C)C)O)O)CO)OC(=O)C(C)CC)OC(=O)/C=C(\C)/CCC=C(C)C)(C)C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H](O8)CO)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1266.71	Volume:	1267.996 ? Van der Waals volume.
Dense:	0.999	LogP:	4.561 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.885 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.047 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	24.0	Rigid Bonds:	48.0
TPSA:	356.81 ? Topological Polar Surface Area.	H-Bond Acceptor:	23.0
H-Bond Donor:	11.0	Rings:	8.0
Heavy Atoms:	23.0

MedChem Properties

QED Drug-Likeness Score:	0.02	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.323	Fsp³:	0.864
MCE-18:	181.252 ? 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:	0.983	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.203	Promiscuous compounds:	0.298

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.325	MDCK Permeability:	-5.163
Pgp-inhibitor:	0.001	Pgp-substrate:	0.007
PAMPA:	0.943 ? 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):	0.002
20% Bioavailability (F20%):	0.346	30% Bioavailability (F30%):	0.959
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.12	MRP1:	0.777
Plasma Protein Binding (PPB):	85.351%	Volume Distribution (VD):	-0.36
Fu:	8.813% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.854

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.023	CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.148	CYP3A4-substrate:	0.985
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.999 ? 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):

0.118

Half-life (T1/2):

2.936

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.02
Human Hepatotoxicity (H-HT):	0.325	Drug-induced Liver Injury (DILI):	0.947
AMES Toxicity:	0.543	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.05	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.999
Hematotoxicity:	0.661	Drug-induced Nephrotoxicity:	0.994
Genotoxicity:	0.012	RPMI-8226 Immunitoxicity:	0.377
A549 Cytotoxicity:	0.95	Hek293 Cytotoxicity:	0.652
BCF:	1.004 ? 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:	4.193 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.349 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.22 ? 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
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	roots	n.a.	n.a.	PMID[15620235]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	roots	Nanning City, Guangxi Province, People's Republic of China	1997-Jan	PMID[17190442]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8121	Symplocos chinensis	Species	Symplocaceae	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

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell line	2

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
NPT180	Cell line	HCT-8	Homo sapiens	IC50	=	2.86	ug/ml	PMID[15620235]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	=	7.29	ug/ml	PMID[15620235]

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 NPC478064 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	22879
0.1-0.2	23308
0.2-0.3	2731
0.3-0.4	691
0.4-0.5	201
0.5-0.6	23
0.6-0.7	11
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC173435
1.0	High Similarity	NPC172374
0.9375	High Similarity	NPC329993
0.9027	High Similarity	NPC134914
0.8448	Intermediate Similarity	NPC301639
0.8448	Intermediate Similarity	NPC478065
0.8293	Intermediate Similarity	NPC69425
0.7541	Intermediate Similarity	NPC475167
0.7258	Intermediate Similarity	NPC329923
0.7258	Intermediate Similarity	NPC475281
0.7087	Intermediate Similarity	NPC475513
0.6977	Remote Similarity	NPC475377
0.6977	Remote Similarity	NPC476074
0.6565	Remote Similarity	NPC262796
0.6565	Remote Similarity	NPC45346
0.6423	Remote Similarity	NPC470914
0.6333	Remote Similarity	NPC478066
0.6324	Remote Similarity	NPC295408
0.6165	Remote Similarity	NPC473755
0.6129	Remote Similarity	NPC470913
0.6094	Remote Similarity	NPC606553
0.6015	Remote Similarity	NPC470912
0.5985	Remote Similarity	NPC329657
0.5891	Remote Similarity	NPC329976
0.5874	Remote Similarity	NPC150893
0.5821	Remote Similarity	NPC264566
0.5692	Remote Similarity	NPC477078
0.5683	Remote Similarity	NPC484833
0.5547	Remote Similarity	NPC46823
0.5524	Remote Similarity	NPC329960
0.5507	Remote Similarity	NPC192765
0.5468	Remote Similarity	NPC178264
0.5417	Remote Similarity	NPC488309
0.5339	Remote Similarity	NPC473586
0.5299	Remote Similarity	NPC609281
0.5224	Remote Similarity	NPC477077
0.5221	Remote Similarity	NPC25998
0.5191	Remote Similarity	NPC235438
0.5069	Remote Similarity	NPC225791
0.5038	Remote Similarity	NPC222580
0.5037	Remote Similarity	NPC477075
0.5036	Remote Similarity	NPC1314
0.5036	Remote Similarity	NPC62725
0.5036	Remote Similarity	NPC273878
0.5036	Remote Similarity	NPC605294

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC478064 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7542
0.1-0.2	1553
0.2-0.3	55
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