NPASS Compound

Natural Product: NPC123854

Natural Product ID	NPC123854
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Poricoic Acid Am
IUPAC Name	(2R)-2-[(2R,3R,3aR,6S,7S,9bR)-2-hydroxy-6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,4,7,8-hexahydrocyclopenta[a]naphthalen-3-yl]-6-methyl-5-methylideneheptanoic acid
Synonyms	Poricoic Acid Am
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1078179
PubChem CID	46882717
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 85 87 0 0 0 0 0 0 0 0999 V2000 5.2164 4.7376 1.1284 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7369 3.5281 1.7139 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3073 2.3502 1.3254 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2398 2.4069 0.4552 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9417 1.0249 1.8216 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6882 0.4144 1.3879 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4005 0.1543 -0.0392 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3954 1.4450 -0.8079 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1708 -0.9673 -0.6467 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4439 -1.6400 -1.7880 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1892 -2.2592 -1.2990 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4753 -1.5489 -0.4445 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9219 -0.2380 -0.0245 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0041 0.6213 0.3775 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4491 0.3206 0.4230 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8405 -0.9303 -0.2573 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2083 -2.0075 0.1215 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3249 -2.1831 1.5944 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4203 -3.1795 -0.5916 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9378 -2.9888 -0.4057 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0382 -1.6437 0.2315 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3487 -0.9623 0.1882 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3415 -1.9568 0.7415 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2710 -2.3872 0.0488 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1884 -2.3752 2.0396 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7997 -0.4346 -1.1040 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1308 0.2607 -1.1183 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2486 1.4852 -0.3371 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 2.1320 0.1681 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6265 2.0352 -0.1216 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4781 1.0838 0.6843 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5554 3.3445 0.6842 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3696 -4.0170 0.4388 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7719 -0.7136 -1.7460 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5248 -0.7012 -1.1128 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5587 -1.2224 -0.4753 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8456 0.1198 -2.3130 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1647 5.0808 1.6224 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4368 5.5211 1.1094 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5228 4.5745 0.0525 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8224 0.3393 1.7816 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8291 1.1719 2.9561 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8449 1.0355 1.8444 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5725 -0.5543 1.9887 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1091 2.2462 -0.0604 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3278 1.7560 -1.2515 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5343 1.4908 -1.5325 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1950 -1.7676 0.1595 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1330 -2.3883 -2.2184 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1474 -0.9158 -2.5760 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8701 -3.2540 -1.6245 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2890 1.6185 0.6989 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9260 1.1694 -0.1539 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8667 0.4486 1.4529 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3793 -2.4487 1.8947 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 -1.3113 2.1876 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3029 -3.0287 1.9492 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1580 -3.2430 -1.6503 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0750 -4.1177 -0.1043 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3853 -3.0958 -1.3856 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8433 -1.8340 1.3368 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3248 -0.1686 0.9527 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8522 -3.0118 2.5032 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8538 -1.1760 -1.9283 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0633 0.3373 -1.4781 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9709 -0.4647 -0.9883 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2619 0.5676 -2.2196 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4169 3.0427 0.7438 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1903 1.8670 0.0521 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1490 2.2524 -1.0645 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3704 0.0729 0.2755 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5455 1.4343 0.5681 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1838 1.1628 1.7514 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0168 4.0751 0.0848 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6245 3.7004 0.7529 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1847 3.1756 1.7073 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1386 -4.5132 0.0236 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7368 0.3886 -1.9576 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2229 -1.0796 -2.0994 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5081 -1.2644 -2.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4080 -1.8456 0.3878 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5646 -1.0420 -0.7905 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9871 0.2870 -2.9786 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4156 1.0438 -2.0652 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5764 -0.4430 -2.9826 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 7 6 1 1 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 22 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 1 0 30 32 1 0 20 33 1 0 16 34 1 6 9 35 1 0 35 36 2 0 35 37 1 0 13 7 1 0 21 16 1 0 17 12 1 0 1 38 1 0 1 39 1 0 1 40 1 0 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 8 45 1 0 8 46 1 0 8 47 1 0 9 48 1 1 10 49 1 0 10 50 1 0 11 51 1 0 14 52 1 0 15 53 1 0 15 54 1 0 18 55 1 0 18 56 1 0 18 57 1 0 19 58 1 0 19 59 1 0 20 60 1 6 21 61 1 1 22 62 1 1 25 63 1 0 26 64 1 0 26 65 1 0 27 66 1 0 27 67 1 0 29 68 1 0 29 69 1 0 30 70 1 0 31 71 1 0 31 72 1 0 31 73 1 0 32 74 1 0 32 75 1 0 32 76 1 0 33 77 1 0 34 78 1 0 34 79 1 0 34 80 1 0 36 81 1 0 36 82 1 0 37 83 1 0 37 84 1 0 37 85 1 0 M END

Standard InCHIKey	WMPHZBWMRPCPKN-XNVOKYKKSA-N
Standard InCHI	InChI=1S/C32H48O5/c1-19(2)21(5)10-11-22(29(35)36)28-26(33)18-32(8)25-13-12-23(20(3)4)30(6,16-15-27(34)37-9)24(25)14-17-31(28,32)7/h13-14,19,22-23,26,28,33H,3,5,10-12,15-18H2,1-2,4,6-9H3,(H,35,36)/t22-,23+,26-,28+,30+,31-,32+/m1/s1
SMILES	COC(=O)CC[C@@]1(C)[C@@H](CC=C2C1=CC[C@]1([C@@]2(C)C[C@H]([C@@H]1[C@H](C(=O)O)CCC(=C)C(C)C)O)C)C(=C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	512.35	Volume:	564.491 ? Van der Waals volume.
Dense:	0.908	LogP:	4.123 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.294 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.504 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	19.0
TPSA:	83.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.246	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.212	Fsp³:	0.688
MCE-18:	67.667 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.935	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.173 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.008 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.413	Promiscuous compounds:	0.221

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.274	MDCK Permeability:	-4.905
Pgp-inhibitor:	0.001	Pgp-substrate:	0.001
PAMPA:	0.708 ? 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%):	0.007	30% Bioavailability (F30%):	0.02
50% Bioavailability (F50%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028	MRP1:	1.0
Plasma Protein Binding (PPB):	91.649%	Volume Distribution (VD):	-0.318
Fu:	8.518% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.183
BSEP inhibitor:	0.993

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.088
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.464
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.713 ? 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):

4.821

Half-life (T1/2):

0.717

ADMET: Toxicity

hERG Blockers:	0.036	hERG Blockers (10um):	0.11
Human Hepatotoxicity (H-HT):	0.476	Drug-induced Liver Injury (DILI):	0.099
AMES Toxicity:	0.141	Rat Oral Acute Toxicity:	0.164
Maximum Recommended Daily Dose:	0.226	Skin Sensitization:	0.762
Carcinogencity:	0.663	Eye Corrosion:	0.011
Eye Irritation:	0.344	Respiratory Toxicity:	0.521
Drug-induced Neurotoxicity:	0.085	Ototoxicity:	0.76
Hematotoxicity:	0.551	Drug-induced Nephrotoxicity:	0.882
Genotoxicity:	0.221	RPMI-8226 Immunitoxicity:	0.091
A549 Cytotoxicity:	0.005	Hek293 Cytotoxicity:	0.028
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:	3.885 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.871 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.906 ? 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
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO33546	Poria coco	Species	n.a.	Eukaryota	n.a.	Yunnan, Kunming, China	n.a.	PMID[17488130]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO6117	Poria	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10608	Exodermis poria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10608	Exodermis poria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO10608	Exodermis poria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO6117	Poria	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	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
Inhibition	4
Activity	1
IC50	2

Activity Type	# Activity
Cell line	2
Organism	4
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[17488130]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	15900.0	nM	PMID[19746919]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	88900.0	nM	PMID[19746919]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0.0	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	9.6	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	57.8	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	81.8	%	PMID[17488130]

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 NPC123854 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	14713
0.1-0.2	31122
0.2-0.3	3859
0.3-0.4	113
0.4-0.5	21
0.5-0.6	14
0.6-0.7	11
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8594	High Similarity	NPC7165
0.8209	Intermediate Similarity	NPC469432
0.7424	Intermediate Similarity	NPC48866
0.7313	Intermediate Similarity	NPC296367
0.6812	Remote Similarity	NPC45324
0.6812	Remote Similarity	NPC162001
0.6667	Remote Similarity	NPC263347
0.662	Remote Similarity	NPC152897
0.6575	Remote Similarity	NPC288464
0.6575	Remote Similarity	NPC477813
0.6575	Remote Similarity	NPC607198
0.6571	Remote Similarity	NPC183546
0.6389	Remote Similarity	NPC484967
0.6338	Remote Similarity	NPC45269
0.6056	Remote Similarity	NPC247406
0.5811	Remote Similarity	NPC186810
0.5811	Remote Similarity	NPC484966
0.5733	Remote Similarity	NPC294480
0.5658	Remote Similarity	NPC155676
0.5526	Remote Similarity	NPC484968
0.5405	Remote Similarity	NPC222845
0.5405	Remote Similarity	NPC296577
0.5395	Remote Similarity	NPC484975
0.5395	Remote Similarity	NPC321301
0.5316	Remote Similarity	NPC484969
0.5263	Remote Similarity	NPC66429
0.5195	Remote Similarity	NPC48647
0.5065	Remote Similarity	NPC77168
0.5065	Remote Similarity	NPC20546

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC123854 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5241
0.1-0.2	3820
0.2-0.3	89
0.3-0.4	0
0.4-0.5	0
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