NPASS Compound

Natural Product: NPC187783

Natural Product ID	NPC187783
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OCMBRGFLKDYVJF-YTFUGFBDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11968418
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 103108 0 0 0 0 0 0 0 0999 V2000 2.3847 -3.8859 1.3243 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2619 -3.5920 -0.1497 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3676 -2.7395 -0.6821 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8244 -1.8551 -1.7685 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8794 -0.7859 -1.2521 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -0.2954 -2.4126 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1645 0.4359 -2.1396 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8752 0.2043 -0.8341 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7930 1.5246 -0.0753 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2675 -0.8269 0.0247 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9793 -1.2858 1.0506 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3431 -0.7664 1.3118 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0698 -0.7764 -0.0212 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5385 -0.3220 0.1332 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2594 -0.9525 -1.0366 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1657 -0.8966 1.3514 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3048 0.1177 2.4824 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1305 1.2939 2.0134 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6520 1.9010 0.7291 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0662 3.2981 1.1094 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5040 1.1397 0.1873 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0538 1.7259 -1.1351 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9556 1.0230 -1.8061 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3484 -0.1571 -1.1412 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1818 -1.2411 -2.2330 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7575 2.2005 -0.1694 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9568 3.3771 -0.6213 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6774 1.2615 -0.6087 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4755 0.8645 1.8975 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0798 -1.3864 -0.1568 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9352 -2.8904 -0.3530 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7488 0.3416 -0.7925 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6556 1.4992 -1.3045 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7021 0.2089 0.2064 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5381 1.2245 0.6716 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4934 1.4275 2.1536 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3887 2.6083 2.4962 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7837 2.3522 1.9616 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7568 1.8609 0.5275 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1384 1.2717 0.2388 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1446 2.2023 0.3721 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8577 0.8250 0.3564 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5262 3.5301 1.9715 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4489 2.7795 3.8658 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2239 1.6248 2.6572 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2069 -4.9045 -0.9018 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0941 -4.7277 -2.2664 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9147 -4.8700 1.4362 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9282 -3.0973 1.8684 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3716 -4.0349 1.7597 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1834 -3.3418 -1.1338 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7486 -2.1182 0.1326 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6906 -1.3274 -2.2232 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3689 -2.4328 -2.6008 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7801 0.3809 -2.9911 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9745 -1.1561 -3.1426 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8796 0.2088 -2.9886 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0192 1.5446 -2.3085 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4120 1.3736 0.9789 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6797 2.1470 -0.1462 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0321 2.1773 -0.5079 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5891 -2.0481 1.7251 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2987 0.2042 1.8057 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8442 -1.4531 2.0102 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2123 -1.8957 -0.1842 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3695 -1.0674 -0.8481 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1487 -0.4644 -1.9884 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9410 -2.0410 -1.0158 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7787 -1.8408 1.7204 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2570 -1.1319 1.1214 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9314 -0.4028 3.2635 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3756 0.3934 2.9631 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1526 2.0423 2.8297 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0498 3.1931 1.4904 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7639 3.7040 1.8709 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1553 3.9518 0.2163 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6467 1.3988 0.8962 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8421 2.8003 -0.9210 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9975 1.7698 -1.7626 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3099 0.7710 -2.8581 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1634 1.7935 -2.0705 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8235 -2.1383 -1.9966 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1778 -1.6563 -2.2736 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5764 -0.8893 -3.2139 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4096 1.4640 -1.2893 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6346 0.0327 2.4039 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6751 -1.2762 0.7994 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2251 -3.3287 0.3514 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5432 -3.0507 -1.3780 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3913 2.1979 0.1718 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9951 0.5300 2.6172 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0058 3.5174 1.9628 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2851 1.5840 2.5684 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6016 2.6656 -0.2058 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3636 0.4295 0.9061 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1941 0.8839 -0.8119 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9010 3.0411 -0.0759 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4315 3.3148 2.2997 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3755 2.8073 4.1581 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1992 1.1949 3.5548 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0890 -5.5439 -0.6464 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3187 -5.5086 -0.5867 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8196 -5.2385 -2.7040 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 7 8 1 0 8 9 1 0 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 19 26 1 0 26 27 2 0 26 28 1 0 18 29 1 0 10 30 1 0 30 31 1 0 5 32 1 0 32 33 2 0 32 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 37 44 1 0 36 45 1 0 2 46 1 0 46 47 1 0 31 2 1 0 42 35 1 0 30 5 1 0 24 8 1 0 24 13 1 0 21 14 1 0 1 48 1 0 1 49 1 0 1 50 1 0 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 9 59 1 0 9 60 1 0 9 61 1 0 11 62 1 0 12 63 1 0 12 64 1 0 13 65 1 0 15 66 1 0 15 67 1 0 15 68 1 0 16 69 1 0 16 70 1 0 17 71 1 0 17 72 1 0 18 73 1 0 20 74 1 0 20 75 1 0 20 76 1 0 21 77 1 0 22 78 1 0 22 79 1 0 23 80 1 0 23 81 1 0 25 82 1 0 25 83 1 0 25 84 1 0 28 85 1 0 29 86 1 0 30 87 1 0 31 88 1 0 31 89 1 0 35 90 1 6 36 91 1 1 37 92 1 6 38 93 1 1 39 94 1 6 40 95 1 0 40 96 1 0 41 97 1 0 43 98 1 0 44 99 1 0 45100 1 0 46101 1 0 46102 1 0 47103 1 0 M END

Standard InCHIKey	OCMBRGFLKDYVJF-YTFUGFBDSA-N
Standard InCHI	InChI=1S/C36H56O11/c1-31(18-38)12-14-36(30(45)47-28-27(42)26(41)25(40)21(17-37)46-28)15-13-33(3)19(20(36)16-31)6-7-22-32(2)10-9-24(39)35(5,29(43)44)23(32)8-11-34(22,33)4/h6,20-28,37-42H,7-18H2,1-5H3,(H,43,44)/t20?,21-,22?,23?,24?,25-,26+,27-,28+,31?,32?,33?,34?,35?,36?/m1/s1
SMILES	CC1(CCC2(CCC3(C)C(=CCC4C5(C)CCC(C(C)(C5CCC34C)C(=O)O)O)C2C1)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	664.38	Volume:	668.656 ? Van der Waals volume.
Dense:	0.994	LogP:	1.93 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.224 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.907 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	34.0
TPSA:	194.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	7.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.169	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.514	Fsp³:	0.889
MCE-18:	131.294 ? 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:	0.581	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.091 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.128	Promiscuous compounds:	0.034

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.802	MDCK Permeability:	-5.119
Pgp-inhibitor:	0.0	Pgp-substrate:	0.154
PAMPA:	1.0 ? 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):	0.647
20% Bioavailability (F20%):	0.096	30% Bioavailability (F30%):	0.897
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038	MRP1:	0.998
Plasma Protein Binding (PPB):	68.189%	Volume Distribution (VD):	-0.372
Fu:	23.645% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.801
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.024	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.473	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.017
HLM stability:	0.021 ? 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):

1.514

Half-life (T1/2):

3.522

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.01
Human Hepatotoxicity (H-HT):	0.671	Drug-induced Liver Injury (DILI):	0.246
AMES Toxicity:	0.376	Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.06	Skin Sensitization:	0.97
Carcinogencity:	0.132	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.009
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.998
Hematotoxicity:	0.21	Drug-induced Nephrotoxicity:	0.611
Genotoxicity:	0.024	RPMI-8226 Immunitoxicity:	0.026
A549 Cytotoxicity:	0.046	Hek293 Cytotoxicity:	0.069
BCF:	0.41 ? 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:	3.953 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.778 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.241 ? 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
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387653]
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19290648]
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	aerial parts	Changqing, Shangdong Province, China	2004-JUN	PMID[19290648]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22325941]
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	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 NPC187783 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	19740
0.1-0.2	24614
0.2-0.3	4219
0.3-0.4	945
0.4-0.5	240
0.5-0.6	85
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	0

Similarity Score	Similarity Level	Natural Product ID
0.7292	Intermediate Similarity	NPC609763
0.7273	Intermediate Similarity	NPC209894
0.7209	Intermediate Similarity	NPC68419
0.6863	Remote Similarity	NPC75287
0.6591	Remote Similarity	NPC237503
0.6559	Remote Similarity	NPC90856
0.6552	Remote Similarity	NPC167383
0.6162	Remote Similarity	NPC473884
0.6087	Remote Similarity	NPC135849
0.6038	Remote Similarity	NPC480474
0.6	Remote Similarity	NPC157868
0.5979	Remote Similarity	NPC29069
0.5978	Remote Similarity	NPC306746
0.5882	Remote Similarity	NPC192791
0.5882	Remote Similarity	NPC242840
0.5806	Remote Similarity	NPC199457
0.58	Remote Similarity	NPC139894
0.5778	Remote Similarity	NPC191763
0.5769	Remote Similarity	NPC40775
0.5769	Remote Similarity	NPC251768
0.5769	Remote Similarity	NPC159309
0.5769	Remote Similarity	NPC11551
0.5769	Remote Similarity	NPC86222
0.5743	Remote Similarity	NPC150400
0.5714	Remote Similarity	NPC214484
0.5714	Remote Similarity	NPC475591
0.5714	Remote Similarity	NPC236870
0.5701	Remote Similarity	NPC281148
0.5699	Remote Similarity	NPC116794
0.5684	Remote Similarity	NPC110139
0.5684	Remote Similarity	NPC108709
0.5638	Remote Similarity	NPC37739
0.5631	Remote Similarity	NPC473343
0.5631	Remote Similarity	NPC475171
0.56	Remote Similarity	NPC48499
0.5591	Remote Similarity	NPC46388
0.5591	Remote Similarity	NPC605954
0.5588	Remote Similarity	NPC473373
0.5579	Remote Similarity	NPC137917
0.5579	Remote Similarity	NPC604133
0.5556	Remote Similarity	NPC114484
0.5545	Remote Similarity	NPC11035
0.5534	Remote Similarity	NPC295371
0.5521	Remote Similarity	NPC271138
0.5521	Remote Similarity	NPC102914
0.5514	Remote Similarity	NPC31193
0.5505	Remote Similarity	NPC301449
0.5505	Remote Similarity	NPC601290
0.549	Remote Similarity	NPC235405
0.549	Remote Similarity	NPC475516
0.5478	Remote Similarity	NPC191827
0.5464	Remote Similarity	NPC220984
0.5437	Remote Similarity	NPC249848
0.5437	Remote Similarity	NPC107966
0.5417	Remote Similarity	NPC7870
0.5417	Remote Similarity	NPC310014
0.5417	Remote Similarity	NPC269315
0.5417	Remote Similarity	NPC75747
0.5412	Remote Similarity	NPC86372
0.5405	Remote Similarity	NPC187290
0.5402	Remote Similarity	NPC155120
0.5402	Remote Similarity	NPC288833
0.5398	Remote Similarity	NPC300419
0.5385	Remote Similarity	NPC39211
0.5377	Remote Similarity	NPC109588
0.5377	Remote Similarity	NPC309714
0.5333	Remote Similarity	NPC469946
0.5327	Remote Similarity	NPC473459
0.5315	Remote Similarity	NPC480473
0.5294	Remote Similarity	NPC179434
0.5283	Remote Similarity	NPC75417
0.5283	Remote Similarity	NPC223301
0.5283	Remote Similarity	NPC171544
0.5283	Remote Similarity	NPC112352
0.5254	Remote Similarity	NPC487505
0.5253	Remote Similarity	NPC256798
0.5248	Remote Similarity	NPC473481
0.5234	Remote Similarity	NPC30735
0.5185	Remote Similarity	NPC10607
0.5185	Remote Similarity	NPC46665
0.5185	Remote Similarity	NPC480475
0.5179	Remote Similarity	NPC481030
0.5172	Remote Similarity	NPC282616
0.5161	Remote Similarity	NPC51564
0.5138	Remote Similarity	NPC63159
0.5138	Remote Similarity	NPC235438
0.51	Remote Similarity	NPC128925
0.5098	Remote Similarity	NPC189884
0.5098	Remote Similarity	NPC138334
0.5091	Remote Similarity	NPC222580
0.5091	Remote Similarity	NPC297263
0.5085	Remote Similarity	NPC470218
0.5052	Remote Similarity	NPC204407
0.5048	Remote Similarity	NPC108748
0.5046	Remote Similarity	NPC102439
0.5041	Remote Similarity	NPC473645

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC187783 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6322
0.1-0.2	2752
0.2-0.3	70
0.3-0.4	6
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