NPASS Compound

Natural Product: NPC5280

Natural Product ID	NPC5280
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-Acetylbetulin
IUPAC Name	[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] acetate
Synonyms	3-O-Acetylbetulin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1087415
PubChem CID	479957
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 87 91 0 0 0 0 0 0 0 0999 V2000 -4.4111 1.7353 -1.4575 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8506 0.5291 -1.7646 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7873 0.4601 -2.9552 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5022 -0.7139 -1.0427 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7685 -1.2292 -0.3755 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4692 -1.3844 1.1021 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9859 -1.6119 1.0864 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2998 -1.2055 2.3651 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8187 -1.2241 2.1882 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3581 -0.2602 1.0802 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5702 1.0895 1.6602 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1550 -0.6051 -0.1268 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6652 0.0467 -1.4044 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2137 -0.4453 -1.5370 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5176 0.2188 -0.3983 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9755 0.4060 -0.6725 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6098 -0.7618 -1.2921 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0582 1.5494 -1.7044 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4384 1.9576 -2.0261 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4897 1.7096 -1.0041 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0304 1.4275 0.3912 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0233 0.4908 1.1037 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1942 2.6767 1.2594 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6303 0.9951 0.5366 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3815 0.0900 1.7009 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8837 0.2292 2.0273 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1380 -0.4524 0.8693 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4496 -1.8998 0.9654 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4651 0.7615 -1.4421 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7703 1.0207 -1.7153 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1484 2.2074 -1.5669 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7465 0.0229 -2.1636 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6080 -0.5062 0.0909 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7058 -2.9876 0.6572 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1444 -3.3565 -0.5811 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6961 2.6283 -2.0152 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7339 1.9147 -0.6308 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7799 0.7810 -2.5494 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8126 -0.5562 -3.3763 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4961 1.2272 -3.7070 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1411 -1.4101 -1.8287 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6183 -0.4966 -0.4950 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1373 -2.1653 -0.8384 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7456 -0.4640 1.6562 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0397 -2.2723 1.4543 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7001 -0.2009 2.6361 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5669 -1.9082 3.1508 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3706 -0.8878 3.1695 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4984 -2.2459 2.0402 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1585 1.0529 2.7168 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0800 1.9269 1.1799 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6283 1.3738 1.8182 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9547 -1.7100 -0.3091 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2733 -0.3164 -2.2305 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5771 1.1448 -1.3260 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2015 -0.2487 -2.5193 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2715 -1.5478 -1.3725 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1007 1.2706 -0.3336 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2825 -1.3671 -0.7020 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1744 -0.5211 -2.2438 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7936 -1.4468 -1.6733 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5393 2.4053 -1.1833 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4976 1.3284 -2.6088 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6947 1.4989 -3.0318 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3689 3.0558 -2.3119 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0918 2.6474 -0.9628 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0324 0.9596 0.9162 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9535 -0.5318 0.7952 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8783 0.5577 2.2004 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2604 2.9571 1.3665 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6899 3.5135 0.7212 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6961 2.5554 2.2333 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0102 1.9270 0.7313 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8909 0.4443 2.6358 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6863 -0.9446 1.5627 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7072 1.3339 1.9600 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6311 -0.2019 2.9948 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5271 -2.1618 2.0646 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4382 -2.2032 0.5659 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2766 -2.5730 0.4511 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0986 -0.5346 -1.2524 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6548 0.5129 -2.5863 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3188 -0.7286 -2.8607 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9614 0.4226 0.6267 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6394 -3.3140 0.7408 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2408 -3.6668 1.3892 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4573 -3.7945 -1.1473 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 1 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 20 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 12 33 1 0 7 34 1 6 34 35 1 0 33 4 1 0 33 7 1 0 27 10 1 0 27 15 1 0 24 16 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 3 40 1 0 4 41 1 6 5 42 1 0 5 43 1 0 6 44 1 0 6 45 1 0 8 46 1 0 8 47 1 0 9 48 1 0 9 49 1 0 11 50 1 0 11 51 1 0 11 52 1 0 12 53 1 6 13 54 1 0 13 55 1 0 14 56 1 0 14 57 1 0 15 58 1 1 17 59 1 0 17 60 1 0 17 61 1 0 18 62 1 0 18 63 1 0 19 64 1 0 19 65 1 0 20 66 1 1 22 67 1 0 22 68 1 0 22 69 1 0 23 70 1 0 23 71 1 0 23 72 1 0 24 73 1 1 25 74 1 0 25 75 1 0 26 76 1 0 26 77 1 0 28 78 1 0 28 79 1 0 28 80 1 0 32 81 1 0 32 82 1 0 32 83 1 0 33 84 1 1 34 85 1 0 34 86 1 0 35 87 1 0 M END

Standard InCHIKey	XUDTWJGGQFHXCR-VFUWXHBOSA-N
Standard InCHI	InChI=1S/C32H52O3/c1-20(2)22-11-16-32(19-33)18-17-30(7)23(27(22)32)9-10-25-29(6)14-13-26(35-21(3)34)28(4,5)24(29)12-15-31(25,30)8/h22-27,33H,1,9-19H2,2-8H3/t22-,23+,24-,25+,26-,27+,29-,30+,31+,32+/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)OC(=O)C)[C@@H]12)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	484.39	Volume:	540.343 ? Van der Waals volume.
Dense:	0.896	LogP:	5.649 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.647 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.298 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	27.0
TPSA:	46.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.332	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.787	Fsp³:	0.906
MCE-18:	102.164 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.96	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.417	Promiscuous compounds:	0.48

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.038	MDCK Permeability:	-4.961
Pgp-inhibitor:	0.605	Pgp-substrate:	0.326
PAMPA:	0.022 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.294	30% Bioavailability (F30%):	0.965
50% Bioavailability (F50%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.878	MRP1:	0.974
Plasma Protein Binding (PPB):	95.219%	Volume Distribution (VD):	-0.056
Fu:	4.673% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.988
OATP1B3 inhibitor:	0.272	BCRP inhibitor:	0.295
BSEP inhibitor:	0.869

ADMET: Metabolism

CYP1A2-inhibitor:	0.004	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.997	CYP2C19-substrate:	0.016
CYP2C9-inhibitor:	0.025	CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.039	CYP2D6-substrate:	0.008
CYP3A4-inhibitor:	0.566	CYP3A4-substrate:	0.81
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.645 ? 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):

7.52

Half-life (T1/2):

0.621

ADMET: Toxicity

hERG Blockers:	0.098	hERG Blockers (10um):	0.285
Human Hepatotoxicity (H-HT):	0.581	Drug-induced Liver Injury (DILI):	0.631
AMES Toxicity:	0.485	Rat Oral Acute Toxicity:	0.214
Maximum Recommended Daily Dose:	0.499	Skin Sensitization:	0.973
Carcinogencity:	0.91	Eye Corrosion:	0.353
Eye Irritation:	0.821	Respiratory Toxicity:	0.819
Drug-induced Neurotoxicity:	0.192	Ototoxicity:	0.309
Hematotoxicity:	0.68	Drug-induced Nephrotoxicity:	0.781
Genotoxicity:	0.685	RPMI-8226 Immunitoxicity:	0.034
A549 Cytotoxicity:	0.197	Hek293 Cytotoxicity:	0.368
BCF:	1.928 ? 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:	4.249 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.579 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.082 ? 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
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[10661881]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11430011]
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	stems	n.a.	n.a.	PMID[12350169]
NPO15915	Edgeworthia gardneri	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387673]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25466012]
NPO15768	Lyonia ovalifolia	Species	Ericaceae	Eukaryota	Twigs; Leaves	n.a.	n.a.	PMID[27792321]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28245113]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[28294414]
NPO16125	Micromonas pusilla	Species	Mamiellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15349	Acacia sparsiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14936	Agave shawii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15205	Alaria crispa	Species	Alariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9479	Ambrosia grayi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13139	Anatheca montagnei	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11808	Ania latifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14807	Arenaria juncea	Species	Scolopacidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11436	Baeomyces roseus	Species	Baeomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5866	Bitis arietans	Species	Viperidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15697	Camellia sasanqua	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26426.1	Cassia javanica subsp. nodosa	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14463	Dirca occidentalis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15797	Drypetes littoralis	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15915	Edgeworthia gardneri	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13442	Eucalyptus regnans	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12293	Euphorbia iberica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24409	Evasterias troschelii	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5047	Evodiopanax innovans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO820	Grindelia perennis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11002	Hopea jucunda	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12490	Lecidea speirodes	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2038	Myrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14313	Pachybasium candidum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16718	Pinna nobilis	Species	Pinnidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16475	Plumbago pulchella	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2827	Plumeria alba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16557	Polygala ruwenzoriensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8804	Raputia simulans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20219	Rhizobium etli	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27733	Rosa hybrid cultivar	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16796	Rumex conglomeratus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4589	Sarcotragus spinosulus	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15588	Senecio desfontainei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11987	Silene inflata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11994	Thesium humile	Species	Thesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16025	Werneria decora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15768	Lyonia ovalifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15768	Lyonia ovalifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26426.1	Cassia javanica subsp. nodosa	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15768	Lyonia ovalifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15697	Camellia sasanqua	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15768	Lyonia ovalifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15915	Edgeworthia gardneri	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16125	Micromonas pusilla	Species	Mamiellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13139	Anatheca montagnei	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11994	Thesium humile	Species	Thesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14936	Agave shawii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2995	Rhododendron formosanum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4589	Sarcotragus spinosulus	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9479	Ambrosia grayi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15797	Drypetes littoralis	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11002	Hopea jucunda	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11987	Silene inflata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16718	Pinna nobilis	Species	Pinnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11436	Baeomyces roseus	Species	Baeomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16557	Polygala ruwenzoriensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15768	Lyonia ovalifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16796	Rumex conglomeratus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15588	Senecio desfontainei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13574	Phaleria cumingii	Species	Tenebrionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16642	Astrantia major	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26426.1	Cassia javanica subsp. nodosa	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14463	Dirca occidentalis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5866	Bitis arietans	Species	Viperidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27733	Rosa hybrid cultivar	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14313	Pachybasium candidum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15205	Alaria crispa	Species	Alariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7987	Tilia vulgaris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13199	Syzygium jambos	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11808	Ania latifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24409	Evasterias troschelii	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14807	Arenaria juncea	Species	Scolopacidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8804	Raputia simulans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16884	Convallaria keiskei	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16025	Werneria decora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16475	Plumbago pulchella	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12490	Lecidea speirodes	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15697	Camellia sasanqua	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5047	Evodiopanax innovans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15349	Acacia sparsiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12293	Euphorbia iberica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13442	Eucalyptus regnans	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19668	Euphorbia characias	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2038	Myrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20219	Rhizobium etli	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO820	Grindelia perennis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13764	Dolichandrone crispa	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2827	Plumeria alba	Species	Apocynaceae	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
Activity	3
IC50	2
EC50	16

Activity Type	# Activity
Cell line	16
Organism	3
Non-molecular	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
NPT857	Cell line	LLC-PK1	Sus scrofa	Activity	=	80.0	%	PMID[26592171]
NPT179	Cell line	A2780	Homo sapiens	EC50	=	11000.0	nM	PMID[26547057]
NPT81	Cell line	A549	Homo sapiens	EC50	=	14000.0	nM	PMID[26547057]
NPT83	Cell line	MCF7	Homo sapiens	EC50	=	11200.0	nM	PMID[26547057]
NPT179	Cell line	A2780	Homo sapiens	EC50	=	28500.0	nM	PMID[27142753]
NPT139	Cell line	HT-29	Homo sapiens	EC50	>	30000.0	nM	PMID[27142753]
NPT83	Cell line	MCF7	Homo sapiens	EC50	=	20200.0	nM	PMID[27142753]
NPT81	Cell line	A549	Homo sapiens	EC50	>	30000.0	nM	PMID[27142753]
NPT165	Cell line	HeLa	Homo sapiens	EC50	>	30000.0	nM	PMID[27142753]
NPT1083	Cell line	A-375	Homo sapiens	EC50	>	30000.0	nM	PMID[31718946]
NPT1216	Cell line	FaDu	Homo sapiens	EC50	>	30000.0	nM	PMID[31718946]
NPT886	Cell line	NIH3T3	Mus musculus	EC50	>	30000.0	nM	PMID[31718946]
NPT856	Organism	Semliki forest virus	Semliki forest virus	Activity	=	3.0	%	PMID[19839605]
NPT856	Organism	Semliki forest virus	Semliki forest virus	IC50	=	24200.0	nM	PMID[19839605]
NPT856	Organism	Semliki forest virus	Semliki forest virus	IC50	=	23988.33	nM	PMID[19839605]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	15200.0	nM	PMID[26547057]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	>	30000.0	nM	PMID[27142753]

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 NPC5280 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	20446
0.1-0.2	23655
0.2-0.3	5255
0.3-0.4	375
0.4-0.5	76
0.5-0.6	26
0.6-0.7	14
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8929	High Similarity	NPC168231
0.7759	Intermediate Similarity	NPC61107
0.7544	Intermediate Similarity	NPC305835
0.7167	Intermediate Similarity	NPC98270
0.6935	Remote Similarity	NPC304194
0.6757	Remote Similarity	NPC148404
0.6757	Remote Similarity	NPC35212
0.6508	Remote Similarity	NPC611062
0.6471	Remote Similarity	NPC471902
0.6393	Remote Similarity	NPC201459
0.6333	Remote Similarity	NPC231256
0.6333	Remote Similarity	NPC178383
0.6324	Remote Similarity	NPC475416
0.629	Remote Similarity	NPC84868
0.6167	Remote Similarity	NPC78067
0.6167	Remote Similarity	NPC278091
0.6053	Remote Similarity	NPC478273
0.6	Remote Similarity	NPC481227
0.5938	Remote Similarity	NPC474233
0.5897	Remote Similarity	NPC310621
0.5735	Remote Similarity	NPC4309
0.5735	Remote Similarity	NPC180204
0.5692	Remote Similarity	NPC474484
0.5692	Remote Similarity	NPC93778
0.5672	Remote Similarity	NPC473742
0.5658	Remote Similarity	NPC474092
0.5658	Remote Similarity	NPC473844
0.5652	Remote Similarity	NPC473690
0.5625	Remote Similarity	NPC119355
0.5616	Remote Similarity	NPC239362
0.5606	Remote Similarity	NPC175410
0.5556	Remote Similarity	NPC472742
0.5522	Remote Similarity	NPC488508
0.5488	Remote Similarity	NPC252133
0.5476	Remote Similarity	NPC478274
0.5469	Remote Similarity	NPC475509
0.5469	Remote Similarity	NPC488509
0.5441	Remote Similarity	NPC261616
0.5385	Remote Similarity	NPC302280
0.5373	Remote Similarity	NPC190940
0.5147	Remote Similarity	NPC474482
0.5143	Remote Similarity	NPC212453
0.5139	Remote Similarity	NPC160506
0.507	Remote Similarity	NPC488503

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC5280 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6663
0.1-0.2	2408
0.2-0.3	74
0.3-0.4	2
0.4-0.5	2
0.5-0.6	1
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
0.5139	Remote Similarity	NPD8035	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