NPASS Compound

Natural Product: NPC81455

Natural Product ID	NPC81455
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZTJFINKUHDHOSM-KEJCWXRGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	15608667
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

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 76 79 0 0 0 0 0 0 0 0999 V2000 -8.3455 -0.4961 0.2527 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0545 -0.6513 -0.5107 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9405 0.0605 0.1901 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6559 -0.1644 -0.5909 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6734 -0.8298 -0.0471 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3469 -1.1248 -0.7111 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3299 -0.6511 -2.1283 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2563 -0.5063 0.0885 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2623 -1.0829 1.5217 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1824 -1.2214 1.9350 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8825 -0.3201 0.9601 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3391 -0.4959 0.8658 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9862 -0.0332 2.1610 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4527 -0.1199 1.9824 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0709 0.0166 0.8408 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5444 -0.0904 0.7891 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1619 0.9773 -0.0728 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2229 1.9793 -0.6073 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8628 1.5708 -0.9761 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3645 0.2769 -0.4241 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6280 -0.7975 -1.4598 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8597 0.3529 -0.2722 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1542 -0.0928 -1.5335 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6737 0.2731 -1.3540 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1437 -0.7064 -0.3340 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3852 -2.1354 -0.6925 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9470 0.3916 -1.0836 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1266 1.5071 0.3190 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1498 2.1317 -0.2037 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1083 2.3040 1.0778 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5442 -1.4769 0.7656 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2026 -0.2742 -0.3863 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2030 0.2237 1.0779 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8268 -1.7410 -0.6409 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2377 -0.2469 -1.5325 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7951 -0.3317 1.2353 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5577 0.2304 -1.5856 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8173 -1.2045 0.9671 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2618 -2.2456 -0.7656 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5578 -1.2351 -2.7088 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2011 0.4380 -2.2288 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3326 -0.9545 -2.5701 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4383 0.5988 0.1988 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8611 -0.4634 2.1942 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6905 -2.1094 1.4628 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2893 -0.8180 2.9786 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5549 -2.2517 1.8746 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6473 0.7292 1.1336 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7218 -1.5120 0.6937 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6116 -0.7081 2.9584 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6414 0.9810 2.4006 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0482 -0.3118 2.8755 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9718 -0.1365 1.8133 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7845 -1.0971 0.3378 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9251 1.4924 0.5863 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1990 2.8545 0.1098 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7121 2.4254 -1.5272 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1363 2.3675 -0.6447 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7196 1.5327 -2.0916 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0699 -1.7477 -1.2213 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3278 -0.3826 -2.4426 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6782 -1.0863 -1.5386 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5262 1.3955 -0.0663 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4811 0.4777 -2.4275 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1661 -1.1881 -1.6783 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1500 0.2570 -2.2999 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5859 1.2843 -0.9157 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4123 -2.2184 -1.8182 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3384 -2.5622 -0.3012 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3931 -2.8313 -0.3165 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4299 1.1397 -1.5161 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9241 1.6647 -0.7592 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2323 3.2158 -0.0699 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3441 2.6191 0.3685 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5820 3.2137 1.5026 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7373 1.6717 1.8896 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 1 0 6 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 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 17 27 1 0 3 28 1 0 28 29 2 0 28 30 1 0 25 8 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 0 2 35 1 0 3 36 1 1 4 37 1 0 5 38 1 0 6 39 1 6 7 40 1 0 7 41 1 0 7 42 1 0 8 43 1 1 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 11 48 1 1 12 49 1 6 13 50 1 0 13 51 1 0 14 52 1 0 16 53 1 0 16 54 1 0 17 55 1 1 18 56 1 0 18 57 1 0 19 58 1 0 19 59 1 0 21 60 1 0 21 61 1 0 21 62 1 0 22 63 1 1 23 64 1 0 23 65 1 0 24 66 1 0 24 67 1 0 26 68 1 0 26 69 1 0 26 70 1 0 27 71 1 0 29 72 1 0 29 73 1 0 30 74 1 0 30 75 1 0 30 76 1 0 M END

Standard InCHIKey	ZTJFINKUHDHOSM-KEJCWXRGSA-N
Standard InCHI	InChI=1S/C29H46O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,20-21,23-27,30H,2,7,11-18H2,1,3-6H3/b9-8+/t20-,21+,23+,24+,25-,26+,27+,28+,29-/m1/s1
SMILES	CC[C@@H](/C=C/[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)C(=C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	410.35	Volume:	476.795 ? Van der Waals volume.
Dense:	0.861	LogP:	6.176 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.651 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.576 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.46	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.746	Fsp³:	0.793
MCE-18:	69.577 ? 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:	0.978	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.667	Promiscuous compounds:	0.162

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.211	MDCK Permeability:	-4.912
Pgp-inhibitor:	0.08	Pgp-substrate:	0.029
PAMPA:	0.003 ? 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%):	0.026	30% Bioavailability (F30%):	0.648
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.009
Plasma Protein Binding (PPB):	98.239%	Volume Distribution (VD):	-0.005
Fu:	1.209% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.986
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.146
CYP2D6-inhibitor:	0.021	CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.565	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.159 ? 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):

12.965

Half-life (T1/2):

0.658

ADMET: Toxicity

hERG Blockers:	0.18	hERG Blockers (10um):	0.295
Human Hepatotoxicity (H-HT):	0.593	Drug-induced Liver Injury (DILI):	0.388
AMES Toxicity:	0.15	Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.766	Skin Sensitization:	0.939
Carcinogencity:	0.899	Eye Corrosion:	0.172
Eye Irritation:	0.971	Respiratory Toxicity:	0.888
Drug-induced Neurotoxicity:	0.097	Ototoxicity:	0.515
Hematotoxicity:	0.479	Drug-induced Nephrotoxicity:	0.404
Genotoxicity:	0.06	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.39	Hek293 Cytotoxicity:	0.708
BCF:	2.79 ? 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:	4.432 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.244 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.13 ? 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]
NPO7657	Plectranthus ornatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398532]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO737	Aspergillus japonicus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO448	Millettia usaramensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26651537]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
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]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO7657	Plectranthus ornatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37226591]
NPO7657	Plectranthus ornatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37764258]
NPO19162	Tsuga heterophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38794396]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO448	Millettia usaramensis	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]
NPO395	Teucrium pilosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11673	Koelreuteria paniculata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9295	Clerodendron fragrans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30239	Clerodendron inerme	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17106	Phyllanthus discoides	Species	Leiothrichidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8403	Annona coriacea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19162	Tsuga heterophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7322	Plagiochila acanthophylla	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10101	Rothmannia macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO737	Aspergillus japonicus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19430	Chondrococcus hornemanni	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12045	Schottera nicaeensis	Species	Phyllophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8424	Juniperus foetidissima	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24555	Coleogyne ramosissima	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3670	Crotalaria podocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17205	Laurencia thyrsifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9461	Gmelina leichhardtii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1786	Pyrus pyrifolia	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30239	Clerodendron inerme	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO17464	Uncaria sessilifructus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19162	Tsuga heterophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9295	Clerodendron fragrans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO1786	Pyrus pyrifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11673	Koelreuteria paniculata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12761	Rheum hotaoense	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7527	Isodon leucophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17106	Phyllanthus discoides	Species	Leiothrichidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18920	Hexalobus crispiflorus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7322	Plagiochila acanthophylla	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11673	Koelreuteria paniculata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7527	Isodon leucophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9295	Clerodendron fragrans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO395	Teucrium pilosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12761	Rheum hotaoense	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3313	Crotalaria trichotoma	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19162	Tsuga heterophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17464	Uncaria sessilifructus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18920	Hexalobus crispiflorus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO448	Millettia usaramensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9015	Solanum arundo	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1786	Pyrus pyrifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17106	Phyllanthus discoides	Species	Leiothrichidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9295	Clerodendron fragrans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11673	Koelreuteria paniculata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30239	Clerodendron inerme	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17106	Phyllanthus discoides	Species	Leiothrichidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9015	Solanum arundo	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14756	Ilex goshiensis	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19005	Engleromyces goetzei	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1786	Pyrus pyrifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17205	Laurencia thyrsifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22170	Actinoplanes awajinensis	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17106	Phyllanthus discoides	Species	Leiothrichidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5310	Eucalyptus bakeri	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11673	Koelreuteria paniculata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16763	Marrubium globosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7566	Ptelea viscosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7322	Plagiochila acanthophylla	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4919	Kalanchoe daigremontiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4982	Notholirion bulbuliferum	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11540	Acacia leptostachya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18920	Hexalobus crispiflorus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3313	Crotalaria trichotoma	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO290	Gibberella lateritium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13095	Pachycereus tehuantepecanus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7527	Isodon leucophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10101	Rothmannia macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19509	Euodia lunu-ankenda	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12761	Rheum hotaoense	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12045	Schottera nicaeensis	Species	Phyllophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8424	Juniperus foetidissima	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24555	Coleogyne ramosissima	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2590	Cordia elaeagnoides	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23815	Isolona campanulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18835	Aloe nobilis	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9887	Protohermes grandis	Species	Corydalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9461	Gmelina leichhardtii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4454	Maytenus salicifolia	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3670	Crotalaria podocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO737	Aspergillus japonicus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8403	Annona coriacea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17464	Uncaria sessilifructus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13706	Barleria acanthoides	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7657	Plectranthus ornatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19162	Tsuga heterophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO395	Teucrium pilosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17461	Hedera canariensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19430	Chondrococcus hornemanni	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO448	Millettia usaramensis	Species	Fabaceae	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 NPC81455 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	22750
0.1-0.2	23772
0.2-0.3	2967
0.3-0.4	236
0.4-0.5	71
0.5-0.6	15
0.6-0.7	32
0.7-0.8	1
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.84	Intermediate Similarity	NPC113733
0.82	Intermediate Similarity	NPC154330
0.7358	Intermediate Similarity	NPC285893
0.7273	Intermediate Similarity	NPC33913
0.7115	Intermediate Similarity	NPC162742
0.7115	Intermediate Similarity	NPC304309
0.7115	Intermediate Similarity	NPC470228
0.7037	Intermediate Similarity	NPC230301
0.6981	Remote Similarity	NPC22105
0.6981	Remote Similarity	NPC34019
0.6981	Remote Similarity	NPC107059
0.6981	Remote Similarity	NPC600590
0.6852	Remote Similarity	NPC136188
0.6852	Remote Similarity	NPC28657
0.6852	Remote Similarity	NPC474216
0.6727	Remote Similarity	NPC198968
0.6727	Remote Similarity	NPC134847
0.6667	Remote Similarity	NPC221758
0.6607	Remote Similarity	NPC241290
0.6607	Remote Similarity	NPC164840
0.6607	Remote Similarity	NPC484739
0.6607	Remote Similarity	NPC209944
0.6607	Remote Similarity	NPC264245
0.6607	Remote Similarity	NPC155986
0.6491	Remote Similarity	NPC328714
0.6491	Remote Similarity	NPC321381
0.6379	Remote Similarity	NPC472265
0.6379	Remote Similarity	NPC318495
0.6379	Remote Similarity	NPC59453
0.6316	Remote Similarity	NPC51014
0.6271	Remote Similarity	NPC603646
0.6167	Remote Similarity	NPC243985
0.6167	Remote Similarity	NPC473943
0.6167	Remote Similarity	NPC280710
0.6167	Remote Similarity	NPC240650
0.6167	Remote Similarity	NPC155011
0.6066	Remote Similarity	NPC474164
0.6066	Remote Similarity	NPC47761
0.6066	Remote Similarity	NPC488870
0.6038	Remote Similarity	NPC96319
0.5965	Remote Similarity	NPC328313
0.5833	Remote Similarity	NPC1272
0.5833	Remote Similarity	NPC470614
0.5781	Remote Similarity	NPC601043
0.5781	Remote Similarity	NPC605412
0.5763	Remote Similarity	NPC234193
0.5738	Remote Similarity	NPC58063
0.5738	Remote Similarity	NPC477522
0.5593	Remote Similarity	NPC76879
0.5517	Remote Similarity	NPC151519
0.5424	Remote Similarity	NPC20688
0.5385	Remote Similarity	NPC474349
0.5385	Remote Similarity	NPC474189
0.5161	Remote Similarity	NPC87604
0.5075	Remote Similarity	NPC176012

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC81455 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7601
0.1-0.2	1391
0.2-0.3	130
0.3-0.4	21
0.4-0.5	2
0.5-0.6	1
0.6-0.7	3
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
0.7037	Intermediate Similarity	NPD7339	Approved
0.6852	Remote Similarity	NPD6942	Phase 4
0.6667	Remote Similarity	NPD4786	Phase 1
0.6038	Remote Similarity	NPD3701	Pre-clinical
0.5517	Remote Similarity	NPD3667	Phase 4

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