NPASS Compound

Natural Product: NPC271494

Natural Product ID	NPC271494
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta,23,28-Trihydroxy-Delta12-Oleanene 23-Caffeate
IUPAC Name	[(3S,4R,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-3-hydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-4-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL501024
PubChem CID	10603919
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 101106 0 0 0 0 0 0 0 0999 V2000 -7.4563 1.3698 1.4957 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4720 2.0992 0.8314 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8235 1.1283 -0.1756 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9485 0.6995 -1.0743 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5194 -0.6332 -0.6536 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4155 -1.6345 -0.9101 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2940 -1.3500 0.0104 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1655 0.0298 0.5584 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7149 0.2489 0.8480 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2323 -0.3481 1.9584 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8404 -0.2564 2.4172 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9962 0.1289 1.2389 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5280 1.3816 0.6565 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8463 1.0723 -0.0213 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6394 2.3649 -0.2657 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9098 1.9999 -0.9996 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5710 0.5101 -1.3745 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8365 2.4561 1.6991 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6180 2.0518 -0.3415 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8388 2.0410 0.1611 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2013 0.6003 0.2848 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4855 0.0591 1.4969 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9330 0.6634 2.7875 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8114 -1.4308 1.5747 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5181 -1.9413 0.3616 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8378 -1.2119 0.2592 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6354 0.2694 0.1842 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5373 0.9693 1.1565 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1272 0.6794 -1.2130 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5191 0.3144 -1.2164 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3314 0.5195 -2.2922 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8612 1.0464 -3.3231 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7605 0.1465 -2.3061 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3342 -0.4147 -1.2619 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7340 -0.8075 -1.2060 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6185 -0.6312 -2.2464 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9570 -1.0204 -2.1633 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4323 -1.6030 -1.0109 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5663 -1.7884 0.0402 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2520 -1.3974 -0.0639 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0675 -2.3798 1.1973 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7678 -2.0034 -0.8978 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5985 -1.5768 1.3870 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0560 -3.0042 -0.5969 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0414 -1.7202 -2.3692 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2035 1.1152 2.4077 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7341 2.4852 1.5431 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9947 2.8959 0.2582 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7947 1.4185 -1.0772 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6370 0.6068 -2.1336 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7480 -0.6867 0.4287 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4096 -0.8226 -1.2852 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3487 -1.7200 -0.4938 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3812 -2.1113 0.8511 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6869 -0.0218 1.5715 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9176 -0.9529 2.5798 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5554 -1.2229 2.8664 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8334 0.4836 3.2404 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1959 -0.6846 0.4724 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0276 2.9641 -0.9696 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9209 2.8656 0.6545 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4256 2.9692 -1.1965 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7174 1.5810 -2.0098 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4336 0.0044 -1.8522 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3933 1.3833 -2.0757 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7337 -0.2116 -1.4245 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7703 2.2625 2.2297 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9732 2.6791 2.3400 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0084 3.4026 1.1054 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5270 1.4574 -1.2988 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9667 3.0718 -0.4919 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8626 2.6249 1.0946 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3900 2.6202 -0.5856 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7118 0.0692 -0.5927 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6141 -0.0335 3.3674 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1295 0.9007 3.5057 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5381 1.5868 2.6944 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0828 -2.0535 1.7330 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4852 -1.6581 2.4523 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9367 -1.9552 -0.5565 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7807 -3.0116 0.5847 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3689 -1.6469 -0.6132 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5788 0.8966 0.7174 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3286 2.0632 1.1734 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6042 0.5056 2.1402 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5733 0.1170 -1.9887 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0177 1.7525 -1.4005 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3680 0.3271 -3.1775 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7218 -0.5955 -0.3867 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3130 -0.1835 -3.1724 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6528 -0.8822 -2.9795 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6082 -1.5653 0.7937 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9667 -3.3690 1.3895 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3098 -1.8515 -0.0550 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3146 -2.2234 1.1652 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0145 -3.0089 -1.1342 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3011 -3.0550 0.4964 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3748 -3.8163 -0.8762 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4415 -0.9041 -2.7534 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4535 -2.6760 -2.4801 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9698 -1.8825 -2.9450 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 1 3 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 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 14 17 1 6 13 18 1 1 13 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 1 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 27 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 39 41 1 0 38 42 1 0 26 43 1 0 6 44 1 0 6 45 1 0 16 3 1 0 27 21 1 0 40 35 1 0 8 3 1 0 14 9 1 0 22 12 1 0 1 46 1 0 2 47 1 0 2 48 1 0 4 49 1 0 4 50 1 0 5 51 1 0 5 52 1 0 7 53 1 0 7 54 1 0 8 55 1 1 10 56 1 0 11 57 1 0 11 58 1 0 12 59 1 6 15 60 1 0 15 61 1 0 16 62 1 0 16 63 1 0 17 64 1 0 17 65 1 0 17 66 1 0 18 67 1 0 18 68 1 0 18 69 1 0 19 70 1 0 19 71 1 0 20 72 1 0 20 73 1 0 21 74 1 6 23 75 1 0 23 76 1 0 23 77 1 0 24 78 1 0 24 79 1 0 25 80 1 0 25 81 1 0 26 82 1 6 28 83 1 0 28 84 1 0 28 85 1 0 29 86 1 0 29 87 1 0 33 88 1 0 34 89 1 0 36 90 1 0 37 91 1 0 40 92 1 0 41 93 1 0 42 94 1 0 43 95 1 0 44 96 1 0 44 97 1 0 44 98 1 0 45 99 1 0 45100 1 0 45101 1 0 M END

Standard InCHIKey	DYOQDMIWQJGRQY-YIEOTUJOSA-N
Standard InCHI	InChI=1S/C39H56O6/c1-34(2)17-19-39(23-40)20-18-37(5)26(27(39)22-34)9-11-31-35(3)15-14-32(43)36(4,30(35)13-16-38(31,37)6)24-45-33(44)12-8-25-7-10-28(41)29(42)21-25/h7-10,12,21,27,30-32,40-43H,11,13-20,22-24H2,1-6H3/b12-8+/t27-,30+,31+,32-,35-,36-,37+,38+,39+/m0/s1
SMILES	OC[C@@]12CCC(C[C@H]2C2=CC[C@H]3[C@@]([C@@]2(CC1)C)(C)CC[C@@H]1[C@]3(C)CC[C@@H]([C@@]1(C)COC(=O)/C=C/c1ccc(c(c1)O)O)O)(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	620.41	Volume:	668.684 ? Van der Waals volume.
Dense:	0.928	LogP:	4.317 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.852 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.884 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	34.0
TPSA:	107.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.116	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.062	Fsp³:	0.718
MCE-18:	161.866 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.969	Fluc inhibitor:	0.938 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.072 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.068 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.156	Promiscuous compounds:	0.102

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.693	MDCK Permeability:	-5.079
Pgp-inhibitor:	0.036	Pgp-substrate:	0.003
PAMPA:	0.99 ? 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%):	0.998	30% Bioavailability (F30%):	0.959
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994	MRP1:	0.392
Plasma Protein Binding (PPB):	97.361%	Volume Distribution (VD):	-0.282
Fu:	2.354% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.143	BCRP inhibitor:	0.683
BSEP inhibitor:	0.973

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.012	CYP2C19-substrate:	0.105
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.005	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.932 ? 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):

9.314

Half-life (T1/2):

1.082

ADMET: Toxicity

hERG Blockers:	0.065	hERG Blockers (10um):	0.293
Human Hepatotoxicity (H-HT):	0.634	Drug-induced Liver Injury (DILI):	0.785
AMES Toxicity:	0.666	Rat Oral Acute Toxicity:	0.309
Maximum Recommended Daily Dose:	0.63	Skin Sensitization:	0.999
Carcinogencity:	0.901	Eye Corrosion:	0.0
Eye Irritation:	0.238	Respiratory Toxicity:	0.558
Drug-induced Neurotoxicity:	0.03	Ototoxicity:	0.799
Hematotoxicity:	0.398	Drug-induced Nephrotoxicity:	0.751
Genotoxicity:	0.958	RPMI-8226 Immunitoxicity:	0.034
A549 Cytotoxicity:	0.949	Hek293 Cytotoxicity:	0.665
BCF:	1.253 ? 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:	4.414 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.129 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.477 ? 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
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	root bark	n.a.	n.a.	PMID[10346965]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	root	n.a.	PMID[10617409]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575966]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29062	Hibiscus syriacus	Species	Malvaceae	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	1
ED50	9

Activity Type	# Activity
Cell line	9
Subcellular	1

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
NPT398	Cell line	UACC-62	Homo sapiens	ED50	=	3.9	ug ml-1	PMID[11473410]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	2.2	ug ml-1	PMID[15104481]
NPT370	Cell line	NCI-H23	Homo sapiens	ED50	=	2.8	ug ml-1	PMID[9036182]
NPT369	Cell line	ACHN	Homo sapiens	ED50	=	1.2	ug ml-1	PMID[26867485]
NPT371	Cell line	UO-31	Homo sapiens	ED50	=	2.0	ug ml-1	PMID[15104481]
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	1.6	ug ml-1	PMID[26642768]
NPT323	Cell line	SW-620	Homo sapiens	ED50	=	1.1	ug ml-1	PMID[9358638]
NPT148	Cell line	HCT-15	Homo sapiens	ED50	=	0.8	ug ml-1	PMID[23571415]
NPT374	Cell line	SF-539	Homo sapiens	ED50	=	1.4	ug ml-1	PMID[26642768]
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	IC50	=	2.3	ug.mL-1	PMID[19344127]

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 NPC271494 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	8043
0.1-0.2	36573
0.2-0.3	4362
0.3-0.4	754
0.4-0.5	95
0.5-0.6	24
0.6-0.7	3
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
0.7191	Intermediate Similarity	NPC155192
0.6632	Remote Similarity	NPC198621
0.6632	Remote Similarity	NPC216940
0.6042	Remote Similarity	NPC235557
0.5679	Remote Similarity	NPC101475
0.5644	Remote Similarity	NPC262970
0.5612	Remote Similarity	NPC182249
0.5612	Remote Similarity	NPC473591
0.5567	Remote Similarity	NPC478270
0.5567	Remote Similarity	NPC478271
0.5385	Remote Similarity	NPC606782
0.5354	Remote Similarity	NPC139243
0.5354	Remote Similarity	NPC116742
0.5333	Remote Similarity	NPC475482
0.5333	Remote Similarity	NPC479747
0.5333	Remote Similarity	NPC479746
0.5333	Remote Similarity	NPC482049
0.5333	Remote Similarity	NPC482050
0.5288	Remote Similarity	NPC54627
0.5288	Remote Similarity	NPC249817
0.5278	Remote Similarity	NPC206232
0.5278	Remote Similarity	NPC14515
0.5238	Remote Similarity	NPC132126
0.5196	Remote Similarity	NPC26045
0.5185	Remote Similarity	NPC479740
0.5185	Remote Similarity	NPC479741
0.5143	Remote Similarity	NPC478272
0.5093	Remote Similarity	NPC479745

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC271494 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4055
0.1-0.2	5039
0.2-0.3	52
0.3-0.4	2
0.4-0.5	1
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
0.5385	Remote Similarity	NPD8166	Discontinued

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