NPASS Compound

Natural Product: NPC298554

Natural Product ID	NPC298554
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3Beta,4Alpha)-3-Hydroxy-23-Oxoolean-12-En-28-Oic Acid
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-9-formyl-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2386825
PubChem CID	92825
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 80 84 0 0 0 0 0 0 0 0999 V2000 5.6283 -0.7521 -2.6499 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8786 -1.2501 -1.8551 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7252 -0.6769 -0.4886 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6827 0.5157 -0.5101 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2463 -1.6464 0.5036 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3242 -1.1603 1.2601 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2901 -2.3039 1.4250 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8614 -1.9154 1.3228 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6731 -0.4204 1.0093 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2999 -0.2506 -0.3567 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9994 1.0857 -0.9676 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8299 1.8072 -0.4384 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7554 1.0511 0.2384 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1890 -0.2814 0.7737 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3045 -0.6854 1.8791 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1017 -0.4579 1.4562 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4579 0.1841 0.3476 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4689 0.7664 -0.6265 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2015 -0.1752 -1.7530 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0152 2.0363 -1.2399 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4008 1.8802 -1.7489 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4038 1.3169 -0.7886 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9316 0.2798 0.1270 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3615 -1.1271 -0.3238 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8440 -1.3164 -0.2816 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4717 -0.0535 -0.8248 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5304 0.7586 -1.6379 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3573 -1.6674 1.0988 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1923 -2.4709 -1.1959 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9747 2.4841 -0.0621 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2053 2.7346 -0.1233 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1377 3.3047 0.6906 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1985 1.9467 1.3596 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2388 0.3905 2.0843 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3156 -2.1314 -2.1630 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6719 1.0164 -1.5188 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7100 0.0504 -0.4308 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5656 1.2150 0.2957 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7532 -2.4928 -0.0643 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2743 -0.2444 1.5300 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2994 -3.4362 1.3532 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5896 -2.1468 2.5070 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2929 -2.5279 0.6107 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3529 -2.0441 2.3240 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6923 -0.9810 -0.9843 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8945 1.7777 -0.9084 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8822 0.9742 -2.0888 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2100 2.5883 0.2912 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4217 2.4624 -1.2660 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0043 -1.0542 -0.0379 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5386 -0.2755 2.8726 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -1.8087 2.0160 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8432 -0.8734 2.1509 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7924 -0.1771 -2.1706 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8811 0.0142 -2.6359 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4709 -1.2021 -1.4273 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3783 2.2200 -2.1575 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8646 2.9233 -0.6054 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7358 2.9152 -2.0681 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4325 1.3091 -2.7017 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4045 0.4213 1.1188 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9995 -1.3521 -1.3407 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9089 -1.8944 0.3463 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3510 -0.3211 -1.4674 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8771 0.5411 -0.0030 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0976 1.6444 -2.0349 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1480 0.2393 -2.5388 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5286 -1.9193 1.8028 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8914 -0.8094 1.5659 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0085 -2.5855 1.0790 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5106 -2.5547 -2.0641 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0787 -3.4096 -0.5892 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2667 -2.4522 -1.4899 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5743 3.9603 1.3332 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8872 1.9740 1.4102 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5614 1.6934 2.3472 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5134 3.0188 1.1821 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6623 1.3525 1.7346 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5935 0.6197 2.9361 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1118 -0.1682 2.5377 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 6 3 5 1 0 5 6 1 0 5 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 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 25 29 1 0 22 30 1 1 30 31 2 0 30 32 1 0 13 33 1 1 9 34 1 1 10 3 1 0 18 13 1 0 27 22 1 0 14 9 1 0 23 17 1 0 2 35 1 0 4 36 1 0 4 37 1 0 4 38 1 0 5 39 1 6 6 40 1 0 7 41 1 0 7 42 1 0 8 43 1 0 8 44 1 0 10 45 1 6 11 46 1 0 11 47 1 0 12 48 1 0 12 49 1 0 14 50 1 6 15 51 1 0 15 52 1 0 16 53 1 0 19 54 1 0 19 55 1 0 19 56 1 0 20 57 1 0 20 58 1 0 21 59 1 0 21 60 1 0 23 61 1 1 24 62 1 0 24 63 1 0 26 64 1 0 26 65 1 0 27 66 1 0 27 67 1 0 28 68 1 0 28 69 1 0 28 70 1 0 29 71 1 0 29 72 1 0 29 73 1 0 32 74 1 0 33 75 1 0 33 76 1 0 33 77 1 0 34 78 1 0 34 79 1 0 34 80 1 0 M END

Standard InCHIKey	QMHCWDVPABYZMC-MYPRUECHSA-N
Standard InCHI	InChI=1S/C30H46O4/c1-25(2)13-15-30(24(33)34)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23(32)27(4,18-31)21(26)9-12-29(22,28)6/h7,18,20-23,32H,8-17H2,1-6H3,(H,33,34)/t20-,21+,22+,23-,26-,27-,28+,29+,30-/m0/s1
SMILES	O=C[C@]1(C)[C@@H](O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(CC1)(C)C)C(=O)O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	511.905 ? Van der Waals volume.
Dense:	0.919	LogP:	3.539 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.169 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.578 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
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:	0.361	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.854	Fsp³:	0.867
MCE-18:	105.857 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.82	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.442	Promiscuous compounds:	0.032

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.498	MDCK Permeability:	-5.106
Pgp-inhibitor:	0.004	Pgp-substrate:	0.001
PAMPA:	1.0 ? 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%):	0.316	30% Bioavailability (F30%):	0.006
50% Bioavailability (F50%):	0.922

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.67	MRP1:	0.896
Plasma Protein Binding (PPB):	94.836%	Volume Distribution (VD):	-0.409
Fu:	5.452% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.067	BCRP inhibitor:	0.031
BSEP inhibitor:	0.992

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.031	CYP2C19-substrate:	0.351
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.008
CYP3A4-inhibitor:	0.005	CYP3A4-substrate:	0.021
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.034
HLM stability:	0.795 ? 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):

4.703

Half-life (T1/2):

0.702

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.015
Human Hepatotoxicity (H-HT):	0.762	Drug-induced Liver Injury (DILI):	0.736
AMES Toxicity:	0.67	Rat Oral Acute Toxicity:	0.65
Maximum Recommended Daily Dose:	0.492	Skin Sensitization:	0.996
Carcinogencity:	0.967	Eye Corrosion:	0.008
Eye Irritation:	0.362	Respiratory Toxicity:	0.899
Drug-induced Neurotoxicity:	0.069	Ototoxicity:	0.593
Hematotoxicity:	0.735	Drug-induced Nephrotoxicity:	0.974
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.061
A549 Cytotoxicity:	0.271	Hek293 Cytotoxicity:	0.193
BCF:	1.366 ? 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:	4.143 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.469 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.999 ? 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
NPO25944	Streptomyces aureofaciens	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14289338]
NPO25944	Streptomyces aureofaciens	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[Ann. N.Y. Acad. Sci., 1948, v51, 177]
NPO25944	Streptomyces aureofaciens	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26555	Phytolacca icosandra	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26555	Phytolacca icosandra	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25944	Streptomyces aureofaciens	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26555	Phytolacca icosandra	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Activity	16
Inhibition	2
IZ	3
MIC	3
IC50	6
ED50	3

Activity Type	# Activity
Individual protein	4
Cell line	18
Organism	10
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1139	Individual protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	Activity	=	100.0	%	PMID[31774676]
NPT324	Individual protein	Cyclooxygenase-1	Ovis aries	Activity	=	100.0	%	PMID[31774676]
NPT31	Individual protein	Cyclooxygenase-2	Homo sapiens	Activity	=	100.0	%	PMID[31774676]
NPT570	Individual protein	Arachidonate 5-lipoxygenase	Homo sapiens	Activity	=	100.0	%	PMID[31774676]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	10400.0	nM	PMID[24941130]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	11900.0	nM	PMID[24941130]
NPT492	Cell line	Caco-2	Homo sapiens	IC50	=	16670.0	nM	PMID[24941130]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	9020.0	nM	PMID[24941130]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	22480.0	nM	PMID[24941130]
NPT116	Cell line	HL-60	Homo sapiens	Activity	=	33.0	%	PMID[24941130]
NPT139	Cell line	HT-29	Homo sapiens	Activity	=	21.0	%	PMID[24941130]
NPT492	Cell line	Caco-2	Homo sapiens	Activity	=	20.0	%	PMID[24941130]
NPT2405	Cell line	SAOS-2	Homo sapiens	Activity	=	36.0	%	PMID[24941130]
NPT83	Cell line	MCF7	Homo sapiens	Activity	=	30.0	%	PMID[24941130]
NPT165	Cell line	HeLa	Homo sapiens	Activity	=	29.0	%	PMID[24941130]
NPT116	Cell line	HL-60	Homo sapiens	Activity	=	4.0	%	PMID[24941130]
NPT139	Cell line	HT-29	Homo sapiens	Activity	=	2.0	%	PMID[24941130]
NPT492	Cell line	Caco-2	Homo sapiens	Activity	=	0.0	%	PMID[24941130]
NPT2405	Cell line	SAOS-2	Homo sapiens	Activity	=	2.0	%	PMID[24941130]
NPT83	Cell line	MCF7	Homo sapiens	Activity	=	4.0	%	PMID[24941130]
NPT165	Cell line	HeLa	Homo sapiens	Activity	=	0.0	%	PMID[24941130]
NPT113	Cell line	RAW264.7	Mus musculus	ED50	=	36.6	uM	PMID[33479679]
NPT1261	Organism	Bacillus thuringiensis	Bacillus thuringiensis	IZ	=	13.0	mm	PMID[24941130]
NPT1261	Organism	Bacillus thuringiensis	Bacillus thuringiensis	MIC	=	32.0	ug.mL-1	PMID[24941130]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	13.0	mm	PMID[24941130]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	32.0	ug.mL-1	PMID[24941130]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	7850.0	nM	PMID[24941130]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	0.0	%	PMID[23662817]
NPT314	Organism	Bacillus cereus	Bacillus cereus	IZ	=	13.0	mm	PMID[24941130]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	32.0	ug.mL-1	PMID[24941130]
NPT842	Organism	Leishmania mexicana	Leishmania mexicana	ED50	=	9.6	uM	PMID[33479679]
NPT842	Organism	Leishmania mexicana	Leishmania mexicana	Inhibition	>=	95.0	%	PMID[33479679]
NPT842	Organism	Leishmania mexicana	Leishmania mexicana	ED50	=	9.6	uM	PMID[37859723]

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 NPC298554 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	22088
0.1-0.2	23562
0.2-0.3	3305
0.3-0.4	524
0.4-0.5	217
0.5-0.6	103
0.6-0.7	38
0.7-0.8	0
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8226	Intermediate Similarity	NPC480946
0.8226	Intermediate Similarity	NPC130577
0.8226	Intermediate Similarity	NPC142415
0.8226	Intermediate Similarity	NPC102683
0.8095	Intermediate Similarity	NPC270768
0.8095	Intermediate Similarity	NPC59263
0.8095	Intermediate Similarity	NPC210106
0.7761	Intermediate Similarity	NPC222047
0.7273	Intermediate Similarity	NPC182797
0.7273	Intermediate Similarity	NPC121798
0.7273	Intermediate Similarity	NPC234346
0.7273	Intermediate Similarity	NPC52169
0.7273	Intermediate Similarity	NPC488562
0.7246	Intermediate Similarity	NPC187933
0.7015	Intermediate Similarity	NPC282616
0.7015	Intermediate Similarity	NPC275809
0.6912	Remote Similarity	NPC158141
0.6866	Remote Similarity	NPC198664
0.6769	Remote Similarity	NPC604575
0.6765	Remote Similarity	NPC64872
0.6765	Remote Similarity	NPC84319
0.6765	Remote Similarity	NPC25906
0.6765	Remote Similarity	NPC52021
0.6765	Remote Similarity	NPC599947
0.6667	Remote Similarity	NPC231063
0.6667	Remote Similarity	NPC282395
0.6667	Remote Similarity	NPC130278
0.6667	Remote Similarity	NPC481360
0.6667	Remote Similarity	NPC110308
0.6575	Remote Similarity	NPC474727
0.6571	Remote Similarity	NPC120840
0.6429	Remote Similarity	NPC106112
0.6429	Remote Similarity	NPC261935
0.6389	Remote Similarity	NPC130520
0.6338	Remote Similarity	NPC200752
0.6338	Remote Similarity	NPC228784
0.6338	Remote Similarity	NPC324341
0.6338	Remote Similarity	NPC601810
0.6296	Remote Similarity	NPC100383
0.6286	Remote Similarity	NPC37038
0.6184	Remote Similarity	NPC188833
0.6145	Remote Similarity	NPC294112
0.6143	Remote Similarity	NPC187722
0.6087	Remote Similarity	NPC280654
0.6056	Remote Similarity	NPC229281
0.6056	Remote Similarity	NPC51700
0.6056	Remote Similarity	NPC88716
0.6056	Remote Similarity	NPC156981
0.6056	Remote Similarity	NPC68160
0.6056	Remote Similarity	NPC606443
0.6047	Remote Similarity	NPC198621
0.6047	Remote Similarity	NPC216940
0.6027	Remote Similarity	NPC474963
0.6	Remote Similarity	NPC204407
0.5972	Remote Similarity	NPC61543
0.5972	Remote Similarity	NPC293048
0.5972	Remote Similarity	NPC225585
0.5972	Remote Similarity	NPC472149
0.5972	Remote Similarity	NPC609452
0.5926	Remote Similarity	NPC283849
0.5926	Remote Similarity	NPC28198
0.5926	Remote Similarity	NPC476123
0.5926	Remote Similarity	NPC606107
0.589	Remote Similarity	NPC202728
0.589	Remote Similarity	NPC158059
0.589	Remote Similarity	NPC291028
0.589	Remote Similarity	NPC293564
0.589	Remote Similarity	NPC136697
0.5867	Remote Similarity	NPC296164
0.5833	Remote Similarity	NPC307282
0.5823	Remote Similarity	NPC603645
0.5811	Remote Similarity	NPC191412
0.5811	Remote Similarity	NPC91010
0.5811	Remote Similarity	NPC114159
0.5811	Remote Similarity	NPC6818
0.5789	Remote Similarity	NPC96580
0.5783	Remote Similarity	NPC286347
0.5765	Remote Similarity	NPC284807
0.5733	Remote Similarity	NPC127689
0.5676	Remote Similarity	NPC29765
0.5658	Remote Similarity	NPC116457
0.5632	Remote Similarity	NPC475472
0.5581	Remote Similarity	NPC473538
0.5541	Remote Similarity	NPC88116
0.5517	Remote Similarity	NPC191410
0.5479	Remote Similarity	NPC474806
0.5479	Remote Similarity	NPC133579
0.5467	Remote Similarity	NPC139570
0.5467	Remote Similarity	NPC209868
0.5455	Remote Similarity	NPC324063
0.5429	Remote Similarity	NPC235341
0.5405	Remote Similarity	NPC171203
0.5405	Remote Similarity	NPC307426
0.5405	Remote Similarity	NPC32118
0.5405	Remote Similarity	NPC98442
0.5405	Remote Similarity	NPC242468
0.5405	Remote Similarity	NPC112866
0.5402	Remote Similarity	NPC18982
0.5395	Remote Similarity	NPC263393
0.5395	Remote Similarity	NPC201657
0.5393	Remote Similarity	NPC270667
0.5393	Remote Similarity	NPC164194
0.5375	Remote Similarity	NPC481362
0.5342	Remote Similarity	NPC477872
0.5341	Remote Similarity	NPC475627
0.5333	Remote Similarity	NPC38754
0.5333	Remote Similarity	NPC271614
0.5325	Remote Similarity	NPC21728
0.5325	Remote Similarity	NPC481316
0.5287	Remote Similarity	NPC43353
0.5281	Remote Similarity	NPC171007
0.5281	Remote Similarity	NPC190849
0.5281	Remote Similarity	NPC475611
0.5275	Remote Similarity	NPC136877
0.5275	Remote Similarity	NPC12288
0.527	Remote Similarity	NPC274330
0.5263	Remote Similarity	NPC145667
0.525	Remote Similarity	NPC601365
0.5222	Remote Similarity	NPC22676
0.5222	Remote Similarity	NPC488215
0.5217	Remote Similarity	NPC174679
0.5217	Remote Similarity	NPC25605
0.5217	Remote Similarity	NPC279554
0.5217	Remote Similarity	NPC56713
0.5217	Remote Similarity	NPC59804
0.5205	Remote Similarity	NPC161751
0.5205	Remote Similarity	NPC474972
0.5205	Remote Similarity	NPC600543
0.52	Remote Similarity	NPC7260
0.52	Remote Similarity	NPC210037
0.52	Remote Similarity	NPC120968
0.52	Remote Similarity	NPC290972
0.52	Remote Similarity	NPC306541
0.52	Remote Similarity	NPC227467
0.52	Remote Similarity	NPC273621
0.5165	Remote Similarity	NPC262970
0.5161	Remote Similarity	NPC114441
0.5161	Remote Similarity	NPC127056
0.5161	Remote Similarity	NPC109079
0.5158	Remote Similarity	NPC469945
0.5135	Remote Similarity	NPC267691
0.5132	Remote Similarity	NPC481314
0.5128	Remote Similarity	NPC471588
0.5109	Remote Similarity	NPC605663
0.5106	Remote Similarity	NPC472949
0.5106	Remote Similarity	NPC6377
0.5106	Remote Similarity	NPC488561
0.5106	Remote Similarity	NPC208381
0.51	Remote Similarity	NPC323359
0.5065	Remote Similarity	NPC173089
0.5063	Remote Similarity	NPC488521
0.5063	Remote Similarity	NPC157113
0.5054	Remote Similarity	NPC132126
0.5053	Remote Similarity	NPC22956
0.5052	Remote Similarity	NPC180550
0.5052	Remote Similarity	NPC35405
0.5049	Remote Similarity	NPC476992

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC298554 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6316
0.1-0.2	2777
0.2-0.3	49
0.3-0.4	4
0.4-0.5	4
0.5-0.6	0
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
		NPD

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