NPASS Compound

Natural Product: NPC30583

Natural Product ID	NPC30583
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Platanic Acid
IUPAC Name	(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-acetyl-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Synonyms	Platanic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL80460
PubChem CID	64980
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

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 79 83 0 0 0 0 0 0 0 0999 V2000 -4.2235 -0.3995 -2.8996 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9219 -1.7232 -2.3191 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6498 -2.6511 -3.0515 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9376 -1.9725 -0.8510 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3520 -1.7572 -0.3431 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2967 -0.5873 0.6500 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8688 -0.7774 1.1582 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1908 -0.8623 -0.1910 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7387 -0.9877 -0.0410 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9798 -1.4235 -1.2718 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4596 -1.6468 -0.7751 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9687 -0.2963 -0.3981 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3232 0.1449 0.8673 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1707 0.2438 0.6183 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4642 1.5401 -0.0190 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8452 0.2658 2.0043 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3409 0.4514 1.8398 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5275 -0.7694 2.0347 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8355 1.5042 1.3158 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3692 1.4291 1.4051 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8367 1.1860 -0.0117 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4688 -0.1840 -0.4612 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1389 -1.3242 0.1918 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8691 -0.2177 -1.9469 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3429 -0.0837 -2.1334 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0622 0.7447 -1.1279 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2333 1.6157 -0.2714 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9399 1.7703 1.0835 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2769 3.0335 -0.8719 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9218 -0.0298 -0.3088 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8746 -1.9851 1.9586 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2030 -2.9847 1.6522 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6381 -2.0731 3.1099 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3762 0.3175 -2.8056 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4279 -0.4979 -3.9761 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0736 0.0385 -2.3398 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5545 -2.9665 -0.6625 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7935 -2.6514 0.0960 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9776 -1.3940 -1.1799 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0430 -0.7804 1.4419 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4245 0.3866 0.1521 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5286 0.0555 -0.7370 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5362 -1.8079 0.6929 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4085 -2.3959 -1.5841 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9953 -0.6401 -2.0233 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9870 -2.1408 -1.5910 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3544 -2.3545 0.0730 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6062 0.4090 -1.2058 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4670 1.7222 -0.3945 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3295 2.3303 0.7838 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7719 1.8527 -0.8285 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4151 1.0455 2.6522 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7142 -0.7671 2.3960 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6132 1.3231 1.2425 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7393 0.5437 2.8922 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0310 -1.7341 1.9857 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5963 -0.9693 2.2731 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1633 -0.2033 2.9455 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4341 1.8043 2.2788 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6793 2.2912 0.5244 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7253 0.7149 2.1375 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6909 2.4592 1.7025 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1836 1.8654 -0.6491 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6905 -1.1081 1.1126 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3620 -2.1376 0.3345 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8826 -1.8507 -0.4823 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3437 0.6503 -2.4314 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5273 -1.1191 -2.4486 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8607 -1.0882 -2.1578 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4961 0.3058 -3.1843 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8018 1.3807 -1.7055 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0479 1.7735 0.9321 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7161 0.9581 1.7696 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6988 2.7637 1.5144 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2793 3.2763 -1.2318 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8098 3.7688 -0.2182 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6297 2.9542 -1.7938 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1081 -0.9014 -0.7114 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3941 -2.7647 3.8129 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 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 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 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 0 27 29 1 0 26 30 1 0 7 31 1 1 31 32 2 0 31 33 1 0 8 4 1 0 14 9 1 0 27 21 1 0 17 7 1 0 22 12 1 0 1 34 1 0 1 35 1 0 1 36 1 0 4 37 1 6 5 38 1 0 5 39 1 0 6 40 1 0 6 41 1 0 8 42 1 6 9 43 1 1 10 44 1 0 10 45 1 0 11 46 1 0 11 47 1 0 12 48 1 6 15 49 1 0 15 50 1 0 15 51 1 0 16 52 1 0 16 53 1 0 17 54 1 0 17 55 1 0 18 56 1 0 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 20 61 1 0 20 62 1 0 21 63 1 6 23 64 1 0 23 65 1 0 23 66 1 0 24 67 1 0 24 68 1 0 25 69 1 0 25 70 1 0 26 71 1 6 28 72 1 0 28 73 1 0 28 74 1 0 29 75 1 0 29 76 1 0 29 77 1 0 30 78 1 0 33 79 1 0 M END

Standard InCHIKey	RVMPLOSJMIQORE-FUAAEJBOSA-N
Standard InCHI	InChI=1S/C29H46O4/c1-17(30)18-9-14-29(24(32)33)16-15-27(5)19(23(18)29)7-8-21-26(4)12-11-22(31)25(2,3)20(26)10-13-28(21,27)6/h18-23,31H,7-16H2,1-6H3,(H,32,33)/t18-,19+,20-,21+,22-,23+,26-,27+,28+,29-/m0/s1
SMILES	CC(=O)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	458.34	Volume:	497.246 ? Van der Waals volume.
Dense:	0.922	LogP:	3.196 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.955 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.377 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	74.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.524	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.673	Fsp³:	0.931
MCE-18:	104.5 ? 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:	0.834	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.34	Promiscuous compounds:	0.142

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.478	MDCK Permeability:	-5.047
Pgp-inhibitor:	0.0	Pgp-substrate:	0.099
PAMPA:	0.997 ? 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):	0.001
20% Bioavailability (F20%):	0.177	30% Bioavailability (F30%):	0.024
50% Bioavailability (F50%):	0.838

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.305	MRP1:	0.994
Plasma Protein Binding (PPB):	97.03%	Volume Distribution (VD):	-0.406
Fu:	3.945% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.978
OATP1B3 inhibitor:	0.778	BCRP inhibitor:	0.014
BSEP inhibitor:	0.382

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.193	CYP2C19-substrate:	0.019
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.033
HLM stability:	0.001 ? 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):

5.84

Half-life (T1/2):

0.88

ADMET: Toxicity

hERG Blockers:	0.053	hERG Blockers (10um):	0.067
Human Hepatotoxicity (H-HT):	0.715	Drug-induced Liver Injury (DILI):	0.636
AMES Toxicity:	0.356	Rat Oral Acute Toxicity:	0.289
Maximum Recommended Daily Dose:	0.502	Skin Sensitization:	0.951
Carcinogencity:	0.925	Eye Corrosion:	0.148
Eye Irritation:	0.787	Respiratory Toxicity:	0.927
Drug-induced Neurotoxicity:	0.039	Ototoxicity:	0.522
Hematotoxicity:	0.478	Drug-induced Nephrotoxicity:	0.763
Genotoxicity:	0.745	RPMI-8226 Immunitoxicity:	0.025
A549 Cytotoxicity:	0.099	Hek293 Cytotoxicity:	0.135
BCF:	0.884 ? 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:	3.497 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.998 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.377 ? 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
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11524125]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11524125]
NPO24136	Melaleuca ericifolia	Species	Myrtaceae	Eukaryota	leaves	Mansoura, Egypt	2006-JAN	PMID[18826277]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	Eukaryota	roots	Xishuangbanna of Yunnan Province, China	n.a.	PMID[21428418]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	root	n.a.	PMID[21428418]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22080044]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25050371]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607351]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33170684]
NPO24416	Artemisia tournefortiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35508595]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39769283]
NPO28686	Syzygium claviflorum	Species	Myrtaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8176401]
NPO25535	Cosmos pringlei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24416	Artemisia tournefortiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5771	Sinularia molesta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24446	Diotis maritima	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21196	Dichotomaria marginata	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25372	Valeriana fedtschenkoi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25263	Aulacomnium androgynum	Species	Aulacomniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28686	Syzygium claviflorum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25705	Cordia curassavica	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24136	Melaleuca ericifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4074	Lonchocarpus orotinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23854	Scilla maritima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25263	Aulacomnium androgynum	Species	Aulacomniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5064	Derris uliginosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25535	Cosmos pringlei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23698	Gardneria insularis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25372	Valeriana fedtschenkoi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25647	Taraxacum bicorne	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24446	Diotis maritima	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO24416	Artemisia tournefortiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24230	Petriella sordida	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5771	Sinularia molesta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6157	Dahlstedtia araripensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25705	Cordia curassavica	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23975	Osteophloeum platyspermum	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21196	Dichotomaria marginata	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29226.1	Ficus cordata subsp. salicifolia	Subspecies	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4074	Lonchocarpus orotinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22144	Daphne lancifolia	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24136	Melaleuca ericifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21967	Astragalus asper	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25862	Lafoensia glyptocarpa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23854	Scilla maritima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28686	Syzygium claviflorum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14279.1	Ficus sarmentosa var. thunbergii	Varieties	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24605	Monochaetia compta	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	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	9
EC50	29
Efficacy	1
Ki	3
GI50	4
PC50	1
Activity	1

Activity Type	# Activity
Individual protein	8
Cell line	36
Organism	1
Non-molecular	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT745	Individual protein	G-protein coupled bile acid receptor 1	Homo sapiens	EC50	=	3110.0	nM	PMID[19911773]
NPT745	Individual protein	G-protein coupled bile acid receptor 1	Homo sapiens	Efficacy	=	156.0	%	PMID[19911773]
NPT540	Individual protein	Bile acid receptor FXR	Homo sapiens	EC50	=	0.0	nM	PMID[19911773]
NPT67	Individual protein	Cholinesterase	Equus caballus	Ki	>	50000.0	nM	PMID[27936444]
NPT761	Individual protein	Protein kinase C epsilon	Homo sapiens	IC50	>	150000.0	nM	PMID[8176401]
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	Ki	=	36860.0	nM	PMID[27936444]
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	Ki	=	31640.0	nM	PMID[27936444]
NPT760	Individual protein	Protein kinase C beta	Homo sapiens	IC50	>	150000.0	nM	PMID[8176401]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell line	HCT-116	Homo sapiens	GI50	>	50000.0	nM	PMID[11527742]
NPT387	Cell line	M14	Homo sapiens	GI50	>	50000.0	nM	PMID[11527742]
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	>	50000.0	nM	PMID[11527742]
NPT403	Cell line	UACC-257	Homo sapiens	GI50	>	50000.0	nM	PMID[11527742]
NPT306	Cell line	PC-3	Homo sapiens	EC50	>	50000000.0	nM	PMID[11527742]
NPT147	Cell line	SK-MEL-2	Homo sapiens	EC50	>	50000000.0	nM	PMID[11527742]
NPT759	Cell line	H9	Homo sapiens	IC50	=	90000.0	nM	PMID[8176401]
NPT179	Cell line	A2780	Homo sapiens	IC50	=	68050.0	nM	PMID[23973824]
NPT1215	Cell line	8505C	Homo sapiens	IC50	=	93600.0	nM	PMID[23973824]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	63230.0	nM	PMID[23973824]
NPT81	Cell line	A549	Homo sapiens	IC50	=	75370.0	nM	PMID[23973824]
NPT1215	Cell line	8505C	Homo sapiens	EC50	=	1570.0	nM	PMID[26177446]
NPT81	Cell line	A549	Homo sapiens	EC50	=	1540.0	nM	PMID[26177446]
NPT139	Cell line	HT-29	Homo sapiens	EC50	=	1690.0	nM	PMID[26177446]
NPT83	Cell line	MCF7	Homo sapiens	EC50	=	1550.0	nM	PMID[26177446]
NPT179	Cell line	A2780	Homo sapiens	EC50	>	30000.0	nM	PMID[28033541]
NPT139	Cell line	HT-29	Homo sapiens	EC50	>	30000.0	nM	PMID[28033541]
NPT83	Cell line	MCF7	Homo sapiens	EC50	>	30000.0	nM	PMID[32956968]
NPT81	Cell line	A549	Homo sapiens	EC50	>	30000.0	nM	PMID[28033541]
NPT1215	Cell line	8505C	Homo sapiens	EC50	>	30000.0	nM	PMID[28033541]
NPT179	Cell line	A2780	Homo sapiens	EC50	=	37000.0	nM	PMID[29197730]
NPT139	Cell line	HT-29	Homo sapiens	EC50	=	36200.0	nM	PMID[29197730]
NPT83	Cell line	MCF7	Homo sapiens	EC50	=	34200.0	nM	PMID[29197730]
NPT81	Cell line	A549	Homo sapiens	EC50	=	47300.0	nM	PMID[29197730]
NPT886	Cell line	NIH3T3	Mus musculus	EC50	=	35400.0	nM	PMID[29197730]
NPT461	Cell line	PANC-1	Homo sapiens	PC50	=	14.2	uM	PMID[32631550]
NPT681	Cell line	PC-12	Rattus norvegicus	EC50	=	170.0	nM	PMID[32738992]
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	96.82	%	PMID[32738992]
NPT1083	Cell line	A-375	Homo sapiens	EC50	>	30000.0	nM	PMID[32956968]
NPT1216	Cell line	FaDu	Homo sapiens	EC50	>	30000.0	nM	PMID[32956968]
NPT886	Cell line	NIH3T3	Mus musculus	EC50	>	30000.0	nM	PMID[32956968]
NPT24664	Cell line	518A2	Homo sapiens	EC50	>	30000.0	nM	PMID[28033541]
NPT24664	Cell line	518A2	Homo sapiens	EC50	=	44800.0	nM	PMID[29197730]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	20000.0	nM	PMID[18826277]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	97470.0	nM	PMID[23973824]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	1500.0	nM	PMID[26177446]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	6500.0	nM	PMID[8176401]

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 NPC30583 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	19877
0.1-0.2	25118
0.2-0.3	3938
0.3-0.4	680
0.4-0.5	191
0.5-0.6	30
0.6-0.7	8
0.7-0.8	1
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
0.7627	Intermediate Similarity	NPC264317
0.7627	Intermediate Similarity	NPC294438
0.7258	Intermediate Similarity	NPC16377
0.7213	Intermediate Similarity	NPC476071
0.7	Intermediate Similarity	NPC472608
0.6719	Remote Similarity	NPC18064
0.6462	Remote Similarity	NPC151191
0.6406	Remote Similarity	NPC488164
0.6406	Remote Similarity	NPC264005
0.6364	Remote Similarity	NPC232112
0.6269	Remote Similarity	NPC488165
0.6	Remote Similarity	NPC97534
0.6	Remote Similarity	NPC195155
0.597	Remote Similarity	NPC2783
0.597	Remote Similarity	NPC606726
0.5909	Remote Similarity	NPC488506
0.5909	Remote Similarity	NPC220498
0.5821	Remote Similarity	NPC201655
0.5775	Remote Similarity	NPC481311
0.5714	Remote Similarity	NPC5767
0.5714	Remote Similarity	NPC475742
0.5538	Remote Similarity	NPC298168
0.5538	Remote Similarity	NPC143133
0.5441	Remote Similarity	NPC474686
0.5441	Remote Similarity	NPC181225
0.5441	Remote Similarity	NPC213832
0.5429	Remote Similarity	NPC601275
0.5373	Remote Similarity	NPC192744
0.5362	Remote Similarity	NPC474512
0.5352	Remote Similarity	NPC252714
0.5323	Remote Similarity	NPC212733
0.5217	Remote Similarity	NPC24772
0.5217	Remote Similarity	NPC30322
0.5211	Remote Similarity	NPC475061
0.519	Remote Similarity	NPC486709
0.5152	Remote Similarity	NPC68828
0.5139	Remote Similarity	NPC486704
0.5072	Remote Similarity	NPC289486
0.5072	Remote Similarity	NPC80590
0.507	Remote Similarity	NPC4309
0.507	Remote Similarity	NPC274330
0.5068	Remote Similarity	NPC169933
0.5068	Remote Similarity	NPC608379

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC30583 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5220
0.1-0.2	3777
0.2-0.3	140
0.3-0.4	9
0.4-0.5	3
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
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
0.7627	Intermediate Similarity	NPD7520	Phase 1

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