NPASS Compound

Natural Product: NPC149543

Natural Product ID	NPC149543
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZEGUWBQDYDXBNS-FVFJQADASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	9846221
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 82 86 0 0 0 0 0 0 0 0999 V2000 4.2986 0.8224 -2.0895 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7853 0.9701 -0.6599 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9179 1.9910 -0.6999 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7033 1.4364 0.2441 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9070 0.4135 0.9511 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4910 0.4320 0.4761 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9091 1.6494 0.5219 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4776 1.8869 0.1002 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2981 0.6331 -0.0351 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7700 0.8606 0.2291 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0956 1.3918 1.5727 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2019 1.9202 -0.7953 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1829 1.3781 -1.7961 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3958 0.7561 -1.1384 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9651 -0.3348 -0.2076 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6742 -0.2490 1.1067 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4366 -1.6538 -0.8454 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4921 -0.4015 -0.1429 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9645 -1.4938 0.7534 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5410 -1.7781 0.3014 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6942 -0.5704 0.5945 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4953 -0.5102 2.0755 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7121 -0.7107 -0.0141 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5849 -0.5291 -1.5345 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3576 -2.0187 0.2442 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4536 -1.9988 1.2867 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4878 -0.9527 1.0228 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4664 -1.0133 2.2090 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2926 -1.3666 -0.1834 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4056 -0.3448 -0.2736 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9145 -2.5860 0.1579 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1386 1.6728 -0.4260 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1946 0.7261 -2.0756 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7086 -0.0658 -2.5929 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5575 1.7074 -2.7057 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0292 2.4639 -1.6743 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8823 1.5677 -0.4031 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7012 2.8206 0.0351 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0191 2.0830 -0.3527 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1780 2.1544 0.9735 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8099 0.7430 2.0358 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4636 2.5332 0.8855 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3970 2.4560 -0.8757 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9266 2.6354 0.7937 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2890 0.4112 -1.1509 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8806 2.2058 1.5048 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2635 1.8817 2.1185 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5408 0.6588 2.2748 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3690 2.3520 -1.3483 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7185 2.7834 -0.2916 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7516 0.7054 -2.5434 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5663 2.2667 -2.3602 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0465 0.3955 -1.9751 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7273 -0.6201 0.9176 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2531 -0.9620 1.8358 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8047 0.7740 1.4923 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6803 -2.0889 -1.4961 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5970 -2.3946 -0.0102 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4201 -1.4890 -1.2989 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1310 -0.6682 -1.1721 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5532 -2.4095 0.5381 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0492 -1.2816 1.8145 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2581 -2.6839 0.8760 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5869 -2.0578 -0.7569 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3632 0.1030 2.3966 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2412 -1.5692 2.3890 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3706 -0.2619 2.6712 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5299 -0.9975 -1.9418 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2255 -1.1117 -1.9643 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6176 0.5112 -1.8443 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7115 -2.8600 0.4995 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8916 -2.3635 -0.6957 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9755 -2.9965 1.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1180 -1.9347 2.3166 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2464 -1.7665 2.0119 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8827 0.0153 2.3627 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8635 -1.2348 3.1139 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7309 -1.4362 -1.1107 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0726 -0.6772 -1.0930 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9775 -0.3252 0.6513 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2280 -3.0090 -0.6868 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9687 2.6088 -0.6870 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 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 15 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 6 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 27 29 1 0 29 30 1 0 29 31 1 0 14 32 1 0 30 2 1 0 27 5 1 0 23 6 1 0 21 9 1 0 18 10 1 0 1 33 1 0 1 34 1 0 1 35 1 0 3 36 1 0 3 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 5 41 1 1 7 42 1 0 8 43 1 0 8 44 1 0 9 45 1 6 11 46 1 0 11 47 1 0 11 48 1 0 12 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 14 53 1 6 16 54 1 0 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 17 59 1 0 18 60 1 6 19 61 1 0 19 62 1 0 20 63 1 0 20 64 1 0 22 65 1 0 22 66 1 0 22 67 1 0 24 68 1 0 24 69 1 0 24 70 1 0 25 71 1 0 25 72 1 0 26 73 1 0 26 74 1 0 28 75 1 0 28 76 1 0 28 77 1 0 29 78 1 6 30 79 1 0 30 80 1 0 31 81 1 0 32 82 1 0 M END

Standard InCHIKey	ZEGUWBQDYDXBNS-FVFJQADASA-N
Standard InCHI	InChI=1S/C30H50O2/c1-25(2)17-20-19-9-10-22-28(6)13-12-23(31)26(3,4)21(28)11-14-30(22,8)29(19,7)16-15-27(20,5)24(32)18-25/h9,20-24,31-32H,10-18H2,1-8H3/t20-,21-,22+,23-,24+,27+,28-,29+,30+/m0/s1
SMILES	CC1(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C)[C@@H](C1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	442.38	Volume:	499.598 ? Van der Waals volume.
Dense:	0.885	LogP:	5.227 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.448 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.974 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	26.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.391	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.724	Fsp³:	0.933
MCE-18:	104.897 ? 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:	0.824	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.02 ? 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:	0.565	Promiscuous compounds:	0.072

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.389	MDCK Permeability:	-5.02
Pgp-inhibitor:	0.65	Pgp-substrate:	0.174
PAMPA:	0.973 ? 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%):	0.913	30% Bioavailability (F30%):	0.377
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.983	MRP1:	0.932
Plasma Protein Binding (PPB):	97.114%	Volume Distribution (VD):	-0.07
Fu:	3.113% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.95	BCRP inhibitor:	0.594
BSEP inhibitor:	0.989

ADMET: Metabolism

CYP1A2-inhibitor:	0.209	CYP1A2-substrate:	0.016
CYP2C19-inhibitor:	0.995	CYP2C19-substrate:	0.492
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.01	CYP2D6-substrate:	0.035
CYP3A4-inhibitor:	0.083	CYP3A4-substrate:	0.188
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.638
HLM stability:	0.806 ? 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):

12.589

Half-life (T1/2):

0.491

ADMET: Toxicity

hERG Blockers:	0.045	hERG Blockers (10um):	0.217
Human Hepatotoxicity (H-HT):	0.491	Drug-induced Liver Injury (DILI):	0.208
AMES Toxicity:	0.363	Rat Oral Acute Toxicity:	0.435
Maximum Recommended Daily Dose:	0.643	Skin Sensitization:	0.933
Carcinogencity:	0.926	Eye Corrosion:	0.048
Eye Irritation:	0.696	Respiratory Toxicity:	0.737
Drug-induced Neurotoxicity:	0.066	Ototoxicity:	0.53
Hematotoxicity:	0.367	Drug-induced Nephrotoxicity:	0.809
Genotoxicity:	0.492	RPMI-8226 Immunitoxicity:	0.068
A549 Cytotoxicity:	0.463	Hek293 Cytotoxicity:	0.478
BCF:	2.154 ? 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:	4.084 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.343 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.844 ? 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
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 17014425]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/bab.1236]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2010.09.006]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO2280	Streptomyces griseochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12964155]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO11789	Swertia decussata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16286309]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO733	Pseudoceratina arabica	Species	Pseudoceratinidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[18598078]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO2280	Streptomyces griseochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19191560]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO12644	Lunularia cruciata	Species	Lunulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO2280	Streptomyces griseochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23377931]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO3292	Desmodium styracifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25620156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO4734	Syzygium nervosum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27797185]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO12644	Lunularia cruciata	Species	Lunulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30848895]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO12644	Lunularia cruciata	Species	Lunulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26606	Macadamia ternifolia	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9640	Dinophysis fortii	Species	Dinophysiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8398	Cymodocea nodosa	Species	Cymodoceaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO733	Pseudoceratina arabica	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9452	Pulsatilla campanella	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11223	Pleurotus japonicus	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2280	Streptomyces griseochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11789	Swertia decussata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7319	Jamesoniella colorata	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8701	Bonamia spectabilis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3292	Desmodium styracifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11910	Peltogyne pubescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3292	Desmodium styracifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7001	Berberis floribunda	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24178	Citrus rugulosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26606	Macadamia ternifolia	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3292	Desmodium styracifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7319	Jamesoniella colorata	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9452	Pulsatilla campanella	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8701	Bonamia spectabilis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7001	Berberis floribunda	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24178	Citrus rugulosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26606	Macadamia ternifolia	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3292	Desmodium styracifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3292	Desmodium styracifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11534	Astragalus spinosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15439	Iyengaria stellata	Species	Scytosiphonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8701	Bonamia spectabilis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6572	Dunalia solanacea	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12169	Ranunculus peltatus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO733	Pseudoceratina arabica	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12864	Trogoderma granarium	Species	Dermestidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11789	Swertia decussata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9009	Atuna racemosa	Species	Chrysobalanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4734	Syzygium nervosum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8006	Berlinia tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9640	Dinophysis fortii	Species	Dinophysiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7001	Berberis floribunda	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7319	Jamesoniella colorata	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3292	Desmodium styracifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23899	Rosulabryum capillare	Species	Bryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2280	Streptomyces griseochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12644	Lunularia cruciata	Species	Lunulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11223	Pleurotus japonicus	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10546	Allagopappus viscosissimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9226	Astragalus pycnanthus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7627	Fumaria micrantha	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24178	Citrus rugulosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8398	Cymodocea nodosa	Species	Cymodoceaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2565	Aglaia australiensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4910	Lepidosperma ustulatum	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18447	Papaver tatricum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11910	Peltogyne pubescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3658	Achillea pseudopectinata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3311	Diplacus longiflorus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9452	Pulsatilla campanella	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26606	Macadamia ternifolia	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7949	Pterodon emarginatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12284	Hydrangea serrata	Species	Hydrangeaceae	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 NPC149543 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	25486
0.1-0.2	20567
0.2-0.3	2758
0.3-0.4	801
0.4-0.5	159
0.5-0.6	58
0.6-0.7	20
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8491	Intermediate Similarity	NPC34177
0.8182	Intermediate Similarity	NPC230295
0.8182	Intermediate Similarity	NPC98386
0.7593	Intermediate Similarity	NPC290598
0.7593	Intermediate Similarity	NPC30590
0.75	Intermediate Similarity	NPC311078
0.7193	Intermediate Similarity	NPC101475
0.7069	Intermediate Similarity	NPC235341
0.678	Remote Similarity	NPC253807
0.678	Remote Similarity	NPC158662
0.6721	Remote Similarity	NPC246708
0.6667	Remote Similarity	NPC7260
0.6667	Remote Similarity	NPC210037
0.6667	Remote Similarity	NPC120968
0.6667	Remote Similarity	NPC227467
0.6667	Remote Similarity	NPC273621
0.6393	Remote Similarity	NPC238992
0.6379	Remote Similarity	NPC27765
0.6379	Remote Similarity	NPC122418
0.6379	Remote Similarity	NPC491014
0.6333	Remote Similarity	NPC196753
0.6269	Remote Similarity	NPC294360
0.6167	Remote Similarity	NPC474989
0.6154	Remote Similarity	NPC488519
0.6129	Remote Similarity	NPC159168
0.6066	Remote Similarity	NPC132478
0.6061	Remote Similarity	NPC18872
0.6061	Remote Similarity	NPC290614
0.5909	Remote Similarity	NPC171203
0.5909	Remote Similarity	NPC307426
0.5909	Remote Similarity	NPC98442
0.5909	Remote Similarity	NPC242468
0.5873	Remote Similarity	NPC470588
0.5833	Remote Similarity	NPC120098
0.5781	Remote Similarity	NPC480950
0.5735	Remote Similarity	NPC49776
0.5735	Remote Similarity	NPC63118
0.5735	Remote Similarity	NPC474436
0.5714	Remote Similarity	NPC40394
0.5714	Remote Similarity	NPC480924
0.5652	Remote Similarity	NPC480919
0.5641	Remote Similarity	NPC224121
0.5625	Remote Similarity	NPC95594
0.5522	Remote Similarity	NPC480946
0.5522	Remote Similarity	NPC213412
0.5522	Remote Similarity	NPC130577
0.5522	Remote Similarity	NPC142415
0.5522	Remote Similarity	NPC102683
0.5522	Remote Similarity	NPC136313
0.5522	Remote Similarity	NPC610937
0.5507	Remote Similarity	NPC164349
0.5469	Remote Similarity	NPC291379
0.5469	Remote Similarity	NPC478657
0.5455	Remote Similarity	NPC40552
0.5441	Remote Similarity	NPC112866
0.5417	Remote Similarity	NPC175006
0.5395	Remote Similarity	NPC167383
0.5373	Remote Similarity	NPC477872
0.5373	Remote Similarity	NPC477579
0.5323	Remote Similarity	NPC601696
0.5312	Remote Similarity	NPC237344
0.5294	Remote Similarity	NPC187722
0.5294	Remote Similarity	NPC2539
0.5286	Remote Similarity	NPC202728
0.5286	Remote Similarity	NPC158059
0.5286	Remote Similarity	NPC228784
0.5286	Remote Similarity	NPC324341
0.5286	Remote Similarity	NPC601810
0.5231	Remote Similarity	NPC475862
0.5217	Remote Similarity	NPC182797
0.5217	Remote Similarity	NPC51700
0.5217	Remote Similarity	NPC88716
0.5217	Remote Similarity	NPC68160
0.5217	Remote Similarity	NPC52169
0.5217	Remote Similarity	NPC488562
0.5217	Remote Similarity	NPC606443
0.5167	Remote Similarity	NPC472805
0.5167	Remote Similarity	NPC90979
0.5152	Remote Similarity	NPC253402
0.5152	Remote Similarity	NPC53744
0.5135	Remote Similarity	NPC471433
0.5135	Remote Similarity	NPC283343
0.5135	Remote Similarity	NPC471432
0.5075	Remote Similarity	NPC133954
0.507	Remote Similarity	NPC293564
0.5067	Remote Similarity	NPC473160

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC149543 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7961
0.1-0.2	1134
0.2-0.3	50
0.3-0.4	3
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
0.5672	Remote Similarity	NPD7645	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