NPASS Compound

Natural Product: NPC184848

Natural Product ID	NPC184848
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Pachymic Acid
IUPAC Name	(2R)-2-[(3S,5R,10S,13R,14R,16R,17R)-3-acetyloxy-16-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
Synonyms	Pachymic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL468034
PubChem CID	5484385
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 90 93 0 0 0 0 0 0 0 0999 V2000 7.6758 1.9093 1.1333 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0353 0.9894 0.0218 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0221 -0.0469 0.5378 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8635 0.1973 -0.5240 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6080 0.3945 -1.8080 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1379 -0.6976 0.3764 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8390 -1.2498 -0.0146 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6710 -0.3193 -0.0472 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4177 -1.0467 -0.5056 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2513 -2.1867 0.5329 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7765 -2.2854 0.8247 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1556 -1.4216 -0.2043 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0063 -2.1770 -1.5002 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1464 -0.8373 0.2101 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6005 0.1395 -0.5615 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8010 0.5484 -1.7256 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6939 0.5476 -1.4817 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1484 -0.2827 -0.3392 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1932 0.5030 0.9563 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9222 0.7479 -0.1753 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6627 1.7113 0.9260 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5380 1.4409 -1.3645 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8385 2.0250 -0.8958 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7900 0.9229 -0.5851 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2510 -0.1687 0.2780 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7657 0.0030 1.7024 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9604 -1.4768 -0.1429 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8004 -0.4136 0.1890 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2933 -1.1402 1.4310 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8103 -1.3699 1.4020 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0362 1.3883 -0.0938 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2325 1.2637 -0.7713 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1773 0.7007 -1.8837 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5450 1.7419 -0.2779 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7127 -3.3841 0.0452 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9391 0.9683 -0.6047 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 1.3136 -1.7451 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6418 1.9251 0.1229 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1306 1.4095 1.9274 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6580 2.3049 1.5394 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1663 2.7990 0.7041 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5611 1.4961 -0.8128 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1279 -0.8938 -0.1576 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0088 0.3793 0.7481 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5969 -0.4291 1.4932 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1977 1.0677 -2.3865 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8206 -0.1430 -2.2850 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0247 -0.1488 1.3640 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8665 -1.5452 0.6236 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8859 -1.6941 -1.0785 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5988 -2.1450 0.6429 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4523 -0.1888 1.1137 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5994 -1.4936 -1.4754 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7977 -1.9415 1.4747 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4168 -3.3440 0.7709 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5449 -1.8995 1.8601 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3294 -3.2396 -1.3161 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0942 -2.2891 -1.7305 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5888 -1.7979 -2.3271 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1017 1.5805 -2.0677 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0379 -0.0832 -2.6334 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1974 0.2446 -2.4175 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9799 1.6218 -1.2967 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4071 -0.0915 1.8441 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0107 1.2816 0.9071 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2658 1.0823 1.1252 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0263 1.2393 1.7311 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0503 2.5434 0.5214 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5229 2.1433 1.4336 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6671 0.7249 -2.2030 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9231 2.3309 -1.6950 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6500 2.7477 -0.1195 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2626 2.5741 -1.7792 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0323 0.4688 -1.5763 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4028 0.8839 2.2031 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5502 -0.8862 2.3302 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8924 0.0154 1.6070 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8134 -2.2487 0.6347 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0000 -1.3011 -0.4152 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3877 -1.8470 -1.0418 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6204 -1.1469 -0.6401 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8224 -2.1170 1.4849 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5295 -0.6026 2.3657 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3040 -0.9701 2.3087 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5992 -2.4803 1.4438 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3779 2.6376 0.3549 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1987 2.0445 -1.1001 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0039 0.9789 0.3914 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8058 -3.4145 -0.9473 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6573 2.9041 -0.1682 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 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 12 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 1 15 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 25 28 1 0 28 29 1 0 29 30 1 0 24 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 10 35 1 0 8 36 1 0 36 37 2 0 36 38 1 0 18 9 1 0 28 20 1 0 18 12 1 0 30 14 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 0 3 43 1 0 3 44 1 0 3 45 1 0 5 46 1 0 5 47 1 0 6 48 1 0 6 49 1 0 7 50 1 0 7 51 1 0 8 52 1 1 9 53 1 6 10 54 1 1 11 55 1 0 11 56 1 0 13 57 1 0 13 58 1 0 13 59 1 0 16 60 1 0 16 61 1 0 17 62 1 0 17 63 1 0 19 64 1 0 19 65 1 0 19 66 1 0 21 67 1 0 21 68 1 0 21 69 1 0 22 70 1 0 22 71 1 0 23 72 1 0 23 73 1 0 24 74 1 6 26 75 1 0 26 76 1 0 26 77 1 0 27 78 1 0 27 79 1 0 27 80 1 0 28 81 1 6 29 82 1 0 29 83 1 0 30 84 1 0 30 85 1 0 34 86 1 0 34 87 1 0 34 88 1 0 35 89 1 0 38 90 1 0 M END

Standard InCHIKey	VDYCLYGKCGVBHN-DRCQUEPLSA-N
Standard InCHI	InChI=1S/C33H52O5/c1-19(2)20(3)10-11-22(29(36)37)28-25(35)18-33(9)24-12-13-26-30(5,6)27(38-21(4)34)15-16-31(26,7)23(24)14-17-32(28,33)8/h19,22,25-28,35H,3,10-18H2,1-2,4-9H3,(H,36,37)/t22-,25-,26+,27+,28+,31-,32-,33+/m1/s1
SMILES	CC(C)C(=C)CC[C@H]([C@H]1[C@@H](C[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](C(C)(C)[C@@H]1CC3)OC(=O)C)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	528.38	Volume:	578.503 ? Van der Waals volume.
Dense:	0.913	LogP:	3.718 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.981 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.131 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	23.0
TPSA:	83.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.267	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.005	Fsp³:	0.818
MCE-18:	87.5 ? 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:	0.978	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? 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:	0.292	Promiscuous compounds:	0.177

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.296	MDCK Permeability:	-4.928
Pgp-inhibitor:	0.365	Pgp-substrate:	0.001
PAMPA:	0.94 ? 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%):	0.071	30% Bioavailability (F30%):	0.089
50% Bioavailability (F50%):	0.95

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	97.022%	Volume Distribution (VD):	-0.477
Fu:	3.258% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.013
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.529 ? 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):

3.423

Half-life (T1/2):

0.793

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.035
Human Hepatotoxicity (H-HT):	0.477	Drug-induced Liver Injury (DILI):	0.277
AMES Toxicity:	0.304	Rat Oral Acute Toxicity:	0.179
Maximum Recommended Daily Dose:	0.147	Skin Sensitization:	0.994
Carcinogencity:	0.717	Eye Corrosion:	0.372
Eye Irritation:	0.779	Respiratory Toxicity:	0.512
Drug-induced Neurotoxicity:	0.026	Ototoxicity:	0.544
Hematotoxicity:	0.593	Drug-induced Nephrotoxicity:	0.94
Genotoxicity:	0.35	RPMI-8226 Immunitoxicity:	0.037
A549 Cytotoxicity:	0.059	Hek293 Cytotoxicity:	0.044
BCF:	0.943 ? 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:	3.99 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.729 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.876 ? 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]
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[COCONUT]
NPO7611	Sclerotium poriae cocos	Species	Typhulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
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[HerDing]
NPO7611	Sclerotium poriae cocos	Species	Typhulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6117	Poria	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7611	Sclerotium poriae cocos	Species	Typhulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10608	Exodermis poria	n.a.	n.a.	n.a.	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
IC50	1
Inhibition	5
Activity	1

Activity Type	# Activity
Individual protein	2
Cell line	1
Organism	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2586	Individual protein	Phospholipase A2, acidic	Naja naja	IC50	=	2897000.0	nM	PMID[8984162]
NPT2586	Individual protein	Phospholipase A2, acidic	Naja naja	Inhibition	=	66.0	%	PMID[8984162]

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]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0.0	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	24.7	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	71.6	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	96.5	%	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 NPC184848 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	16728
0.1-0.2	27849
0.2-0.3	4933
0.3-0.4	255
0.4-0.5	60
0.5-0.6	19
0.6-0.7	7
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
0.8889	High Similarity	NPC484973
0.8462	Intermediate Similarity	NPC69548
0.7313	Intermediate Similarity	NPC474889
0.7273	Intermediate Similarity	NPC23434
0.6944	Remote Similarity	NPC288464
0.6944	Remote Similarity	NPC477813
0.6944	Remote Similarity	NPC607198
0.6812	Remote Similarity	NPC54689
0.6522	Remote Similarity	NPC484974
0.6479	Remote Similarity	NPC183546
0.6027	Remote Similarity	NPC484976
0.5811	Remote Similarity	NPC148414
0.5811	Remote Similarity	NPC243866
0.5811	Remote Similarity	NPC111585
0.5811	Remote Similarity	NPC175628
0.5753	Remote Similarity	NPC76895
0.5641	Remote Similarity	NPC484969
0.5479	Remote Similarity	NPC55309
0.5479	Remote Similarity	NPC28252
0.5405	Remote Similarity	NPC473269
0.5256	Remote Similarity	NPC294480
0.5238	Remote Similarity	NPC195708
0.5195	Remote Similarity	NPC45324
0.5195	Remote Similarity	NPC484971
0.5195	Remote Similarity	NPC162001
0.5195	Remote Similarity	NPC484970
0.519	Remote Similarity	NPC42042
0.5132	Remote Similarity	NPC155479
0.5065	Remote Similarity	NPC46281
0.506	Remote Similarity	NPC473514

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC184848 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5222
0.1-0.2	3798
0.2-0.3	127
0.3-0.4	3
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