NPASS Compound

Natural Product: NPC78681

Natural Product ID	NPC78681
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YPOBUDKLSCZLJL-OLZYCKSRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	49871377
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 104109 0 0 0 0 0 0 0 0999 V2000 -6.4729 0.4397 -3.0748 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9059 -0.3568 -1.8320 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7020 0.5066 -0.9369 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3306 0.4624 0.5031 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8114 0.4853 0.7199 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2215 1.7976 0.3670 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9740 1.8198 -0.4076 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0619 0.6692 -0.4150 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6819 0.3542 -1.8801 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7415 -0.5664 0.0398 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0265 -1.6159 0.3988 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5857 -1.6588 0.3807 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9626 -0.3419 0.1766 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3855 -0.3403 0.8960 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3118 -0.5511 2.3441 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1313 -1.5062 0.2754 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5785 -1.5411 0.7147 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2418 -0.2554 0.1980 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5651 0.9620 0.7216 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1064 2.1462 -0.0578 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8604 1.2773 2.1582 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0910 0.8967 0.4058 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3208 2.1390 0.7040 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0035 2.0653 -0.0616 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7661 0.8776 0.3907 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1994 1.1472 1.7979 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5800 -0.3219 0.1771 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2510 -0.5186 -0.9741 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2571 0.5672 -1.2277 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5231 0.0831 -1.8764 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0880 -1.1733 -1.3309 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1095 -1.8415 -0.4264 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3037 -1.4870 0.9994 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4325 -1.1508 1.8008 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6235 -1.5457 1.4694 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9186 -1.2240 2.8239 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8423 -1.7821 -0.8940 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3942 -2.0716 -2.3775 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4162 1.1603 -1.8563 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7303 1.5001 -2.1614 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2504 -0.7149 0.0744 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7911 -1.1221 -1.2488 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0834 -2.6339 -1.2683 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7136 0.3003 2.2003 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2324 1.1892 2.9325 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1615 -0.8685 2.7631 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2616 0.4514 -3.8528 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5632 0.0443 -3.5228 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3822 1.5073 -2.7376 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6344 -1.1076 -2.2749 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5865 1.5729 -1.2731 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7976 0.3214 -1.0001 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7270 -0.4485 0.9932 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7263 1.3291 1.0676 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1886 2.4508 1.2945 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0282 2.3478 -0.2166 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4290 2.7552 -0.0669 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2301 2.1097 -1.4763 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5545 -0.7432 -2.0348 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4846 0.7739 -2.5530 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7626 0.8211 -2.2054 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5627 -2.5154 0.7320 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2132 -2.1964 1.3031 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2997 -2.4081 -0.4326 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6437 -0.3051 -0.9147 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6090 0.2702 3.0089 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7107 -0.8522 2.7292 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9442 -1.4302 2.6837 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1446 -1.3851 -0.8456 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6833 -2.4737 0.5195 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7392 -1.7275 1.7635 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0486 -2.3594 0.1326 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9192 -0.3224 -0.8892 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2340 2.1397 0.0088 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7784 3.1220 0.3766 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8657 2.0863 -1.1339 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1250 2.0373 2.4941 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8517 1.8234 2.2132 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9856 0.4174 2.8112 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0618 0.8002 -0.7075 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2059 2.3717 1.7645 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8446 3.0054 0.2490 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6917 2.0951 -1.1153 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4689 3.0503 0.1433 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4189 1.4259 2.5056 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8982 2.0095 1.7663 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7513 0.3065 2.2565 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6244 -0.5883 -1.8904 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4601 1.1836 -0.3131 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2826 -0.0784 -2.9681 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0702 -1.0074 -0.8081 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3854 -2.9479 -0.4626 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4837 -2.0311 3.3327 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0341 -0.9008 3.3755 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6352 -0.3585 2.7644 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5159 -2.4670 -2.6544 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2837 0.9548 -2.2615 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2911 2.3024 -2.2028 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4897 -1.5728 0.7776 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9320 -1.0494 -1.9868 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6199 -2.9435 -0.3422 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0861 -3.1615 -1.2165 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5912 -2.9124 -2.1948 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7554 -1.2489 3.6303 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 6 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 18 27 1 0 27 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 2 0 33 35 1 0 35 36 1 0 32 37 1 0 31 38 1 0 30 39 1 0 29 40 1 0 10 41 1 0 41 42 1 0 42 43 1 0 5 44 1 1 44 45 2 0 44 46 1 0 42 2 1 0 41 5 1 0 25 8 1 0 37 28 1 0 25 13 1 0 22 14 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 6 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 6 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 6 20 74 1 0 20 75 1 0 20 76 1 0 21 77 1 0 21 78 1 0 21 79 1 0 22 80 1 6 23 81 1 0 23 82 1 0 24 83 1 0 24 84 1 0 26 85 1 0 26 86 1 0 26 87 1 0 28 88 1 6 29 89 1 1 30 90 1 6 31 91 1 1 32 92 1 1 36 93 1 0 36 94 1 0 36 95 1 0 38 96 1 0 39 97 1 0 40 98 1 0 41 99 1 1 42100 1 6 43101 1 0 43102 1 0 43103 1 0 46104 1 0 M END

Standard InCHIKey	YPOBUDKLSCZLJL-OLZYCKSRSA-N
Standard InCHI	InChI=1S/C37H58O9/c1-19-11-16-37(32(42)43)18-17-35(6)21(25(37)20(19)2)9-10-23-34(5)14-13-24(33(3,4)22(34)12-15-36(23,35)7)45-31-28(40)26(38)27(39)29(46-31)30(41)44-8/h9,19-20,22-29,31,38-40H,10-18H2,1-8H3,(H,42,43)/t19-,20+,22+,23-,24+,25+,26+,27+,28-,29+,31-,34+,35-,36-,37+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](C(=O)OC)O3)O)O)O)[C@@H]2[C@H]1C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	646.41	Volume:	668.372 ? Van der Waals volume.
Dense:	0.967	LogP:	3.199 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.245 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.022 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	34.0
TPSA:	142.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.187	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.339	Fsp³:	0.892
MCE-18:	127.571 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.969	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.071 ? 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:	0.168	Promiscuous compounds:	0.193

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.481	MDCK Permeability:	-5.034
Pgp-inhibitor:	0.002	Pgp-substrate:	0.001
PAMPA:	0.988 ? 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):	0.019
20% Bioavailability (F20%):	0.52	30% Bioavailability (F30%):	0.68
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013	MRP1:	0.487
Plasma Protein Binding (PPB):	77.054%	Volume Distribution (VD):	-0.51
Fu:	20.229% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.034
BSEP inhibitor:	0.882

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.888
HLM stability:	0.0 ? 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):

1.114

Half-life (T1/2):

2.205

ADMET: Toxicity

hERG Blockers:	0.04	hERG Blockers (10um):	0.115
Human Hepatotoxicity (H-HT):	0.583	Drug-induced Liver Injury (DILI):	0.9
AMES Toxicity:	0.196	Rat Oral Acute Toxicity:	0.089
Maximum Recommended Daily Dose:	0.172	Skin Sensitization:	0.952
Carcinogencity:	0.383	Eye Corrosion:	0.0
Eye Irritation:	0.149	Respiratory Toxicity:	0.321
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.703
Hematotoxicity:	0.308	Drug-induced Nephrotoxicity:	0.912
Genotoxicity:	0.408	RPMI-8226 Immunitoxicity:	0.049
A549 Cytotoxicity:	0.032	Hek293 Cytotoxicity:	0.194
BCF:	1.664 ? 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:	4.376 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.786 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.25 ? 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
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[16792421]
NPO14784	Hydnocarpus wightiana	Species	Achariaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1800632]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	whole plants	Panshi, Jilin Province, China	2009-JUN	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25453801]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26702644]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28383891]
NPO14532	Salmea scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37278000]
NPO7413	Wedelia biflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9501	Melaleuca leucadendron	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17369	Onobrychis bobrovi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7990	Salsola somalensis	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25947	Bejaranoa semistriata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17753	Carex kobomugi	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17087	Plagiomnium affine	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14784	Hydnocarpus wightiana	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17753	Carex kobomugi	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14784	Hydnocarpus wightiana	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7990	Salsola somalensis	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7413	Wedelia biflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25041	Virola bicuhyba	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17087	Plagiomnium affine	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9931	Cryptocarya caloneura	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9501	Melaleuca leucadendron	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15889	Campanula biebersteiniana	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11738	Talaromyces emodensis	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14532	Salmea scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29294	Rotheca myricoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1804	Grevillea pyramidalis	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6000	Helichrysum panduratum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17369	Onobrychis bobrovi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25947	Bejaranoa semistriata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12155	Wrightia mollissima	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27844	Coreopsis verticillata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14784	Hydnocarpus wightiana	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17753	Carex kobomugi	Species	Cyperaceae	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 NPC78681 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	17009
0.1-0.2	27109
0.2-0.3	4382
0.3-0.4	867
0.4-0.5	386
0.5-0.6	78
0.6-0.7	17
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
0.75	Intermediate Similarity	NPC57362
0.7111	Intermediate Similarity	NPC473481
0.7011	Intermediate Similarity	NPC177246
0.6875	Remote Similarity	NPC485589
0.6809	Remote Similarity	NPC108748
0.6735	Remote Similarity	NPC180550
0.6735	Remote Similarity	NPC35405
0.6548	Remote Similarity	NPC485586
0.6548	Remote Similarity	NPC485588
0.6517	Remote Similarity	NPC606107
0.6471	Remote Similarity	NPC230151
0.6337	Remote Similarity	NPC258885
0.62	Remote Similarity	NPC469945
0.618	Remote Similarity	NPC484195
0.6154	Remote Similarity	NPC283849
0.6098	Remote Similarity	NPC51700
0.6098	Remote Similarity	NPC88716
0.6098	Remote Similarity	NPC68160
0.6044	Remote Similarity	NPC274507
0.6	Remote Similarity	NPC485585
0.5978	Remote Similarity	NPC485882
0.5957	Remote Similarity	NPC485587
0.5895	Remote Similarity	NPC173569
0.5876	Remote Similarity	NPC214484
0.587	Remote Similarity	NPC204407
0.5851	Remote Similarity	NPC286347
0.5833	Remote Similarity	NPC61543
0.5833	Remote Similarity	NPC293048
0.5833	Remote Similarity	NPC225585
0.5816	Remote Similarity	NPC164194
0.58	Remote Similarity	NPC56713
0.5765	Remote Similarity	NPC173089
0.5743	Remote Similarity	NPC114441
0.5743	Remote Similarity	NPC127056
0.5684	Remote Similarity	NPC31839
0.5644	Remote Similarity	NPC25605
0.5619	Remote Similarity	NPC104400
0.5619	Remote Similarity	NPC10320
0.5588	Remote Similarity	NPC109079
0.5534	Remote Similarity	NPC472949
0.55	Remote Similarity	NPC211798
0.5495	Remote Similarity	NPC62725
0.549	Remote Similarity	NPC304110
0.549	Remote Similarity	NPC27518
0.549	Remote Similarity	NPC611516
0.5481	Remote Similarity	NPC22956
0.5476	Remote Similarity	NPC274050
0.5476	Remote Similarity	NPC162632
0.5474	Remote Similarity	NPC28198
0.5474	Remote Similarity	NPC476123
0.5465	Remote Similarity	NPC71074
0.5465	Remote Similarity	NPC605937
0.5464	Remote Similarity	NPC100383
0.5455	Remote Similarity	NPC480951
0.5402	Remote Similarity	NPC87095
0.5402	Remote Similarity	NPC32407
0.5402	Remote Similarity	NPC263548
0.5402	Remote Similarity	NPC606320
0.5392	Remote Similarity	NPC136877
0.5385	Remote Similarity	NPC6377
0.5385	Remote Similarity	NPC488561
0.5385	Remote Similarity	NPC208381
0.5377	Remote Similarity	NPC114304
0.537	Remote Similarity	NPC257468
0.5347	Remote Similarity	NPC270667
0.5341	Remote Similarity	NPC113989
0.5321	Remote Similarity	NPC79718
0.5315	Remote Similarity	NPC488564
0.5306	Remote Similarity	NPC242611
0.5283	Remote Similarity	NPC223301
0.5283	Remote Similarity	NPC171544
0.5278	Remote Similarity	NPC118033
0.5248	Remote Similarity	NPC480938
0.5238	Remote Similarity	NPC488516
0.5233	Remote Similarity	NPC274330
0.5227	Remote Similarity	NPC120840
0.5227	Remote Similarity	NPC477288
0.5225	Remote Similarity	NPC324875
0.5225	Remote Similarity	NPC292677
0.52	Remote Similarity	NPC294112
0.52	Remote Similarity	NPC284807
0.5192	Remote Similarity	NPC174679
0.5192	Remote Similarity	NPC279554
0.5192	Remote Similarity	NPC59804
0.5182	Remote Similarity	NPC119794
0.5098	Remote Similarity	NPC30397
0.5098	Remote Similarity	NPC475472
0.5096	Remote Similarity	NPC12288
0.5094	Remote Similarity	NPC39211
0.5091	Remote Similarity	NPC481082
0.5091	Remote Similarity	NPC73829
0.5091	Remote Similarity	NPC164419
0.5057	Remote Similarity	NPC477289
0.5056	Remote Similarity	NPC305464
0.5056	Remote Similarity	NPC19376
0.5056	Remote Similarity	NPC25848
0.5047	Remote Similarity	NPC80843
0.5045	Remote Similarity	NPC262199

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC78681 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5873
0.1-0.2	3201
0.2-0.3	65
0.3-0.4	9
0.4-0.5	2
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