NPASS Compound

Natural Product: NPC141401

Natural Product ID	NPC141401
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ganoderic Acid S
IUPAC Name	(E,5S,6S)-5-acetyloxy-6-[(3R,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylhept-2-enoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3785282
PubChem CID	21637705
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 88 0 0 0 0 0 0 0 0999 V2000 6.5926 0.1611 -2.2920 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8889 1.4117 -1.9788 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7157 1.3658 -1.3953 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0237 0.1043 -1.0157 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7704 0.0413 0.4711 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0750 -1.2035 0.9030 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8887 -1.2083 2.4221 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8006 -1.5403 0.1987 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3408 -2.8704 0.8310 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1107 -2.6627 1.2021 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5175 -1.6495 0.2156 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6201 -2.2484 -1.1543 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7202 -0.8728 0.5484 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4966 -1.1091 1.5902 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6734 -0.2075 1.7570 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2769 -0.0765 0.3520 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7055 0.3641 0.4037 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9470 1.5257 1.3239 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5055 -0.8187 0.9661 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1898 0.5947 -0.9905 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2704 -0.0473 -2.0229 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8845 0.5674 -1.9655 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4043 0.7395 -0.5353 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3754 2.1954 -0.2168 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0115 0.2151 -0.3785 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9918 0.7055 -1.0610 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4085 0.2344 -0.9526 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6576 -0.6401 0.2615 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4218 0.1751 1.4729 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4541 0.0031 -1.1871 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0760 -0.0127 1.0775 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5632 1.0028 1.8536 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8769 2.0154 2.0573 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9339 0.8948 2.4630 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4881 2.6780 -2.3125 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6219 2.7393 -2.8769 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8674 3.8895 -2.0393 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1128 -0.4182 -3.0955 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6997 -0.4769 -1.3832 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6370 0.3680 -2.6331 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1915 2.2857 -1.1617 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1303 0.0090 -1.6480 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6522 -0.7887 -1.2711 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2799 0.9924 0.7374 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7703 -2.0420 0.6866 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2768 -0.2461 2.8150 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5691 -1.9730 2.9097 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8910 -1.4890 2.7448 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0568 -1.7714 -0.8547 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9718 -3.1974 1.6495 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3474 -3.6878 0.0769 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2686 -2.4070 2.2533 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7037 -3.6028 1.0064 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4388 -1.7757 -1.7600 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9055 -3.3380 -1.1158 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2853 -2.1860 -1.7616 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2563 -1.9142 2.2520 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4292 -0.6177 2.4443 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3203 0.8055 2.0391 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2797 -1.1195 -0.0503 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6654 1.2861 2.1494 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4589 2.3457 0.7438 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0333 1.8951 1.8254 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5413 -0.8074 0.6303 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4684 -0.7563 2.0905 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0162 -1.7803 0.7159 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2815 1.6552 -1.2748 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2455 -1.1507 -1.9219 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7205 0.1738 -3.0125 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9031 1.5350 -2.5138 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2137 -0.1335 -2.5208 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3402 2.7104 -0.3230 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6769 2.6844 -0.9331 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9104 2.3692 0.7948 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1799 1.5085 -1.7511 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0235 1.1649 -0.7968 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7558 -0.2076 -1.8903 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2623 0.6698 1.9388 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2903 1.0144 1.1943 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1481 -0.3611 2.2739 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3595 -0.9711 -1.3971 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5515 1.6748 1.9784 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8927 1.0071 3.5614 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3770 -0.0806 2.2426 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4642 4.6891 -1.8862 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 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 6 11 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 17 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 1 23 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 1 20 30 1 0 5 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 2 35 1 0 35 36 2 0 35 37 1 0 28 8 1 0 28 11 1 0 25 13 1 0 23 16 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 5 44 1 1 6 45 1 1 7 46 1 0 7 47 1 0 7 48 1 0 8 49 1 6 9 50 1 0 9 51 1 0 10 52 1 0 10 53 1 0 12 54 1 0 12 55 1 0 12 56 1 0 14 57 1 0 15 58 1 0 15 59 1 0 16 60 1 6 18 61 1 0 18 62 1 0 18 63 1 0 19 64 1 0 19 65 1 0 19 66 1 0 20 67 1 6 21 68 1 0 21 69 1 0 22 70 1 0 22 71 1 0 24 72 1 0 24 73 1 0 24 74 1 0 26 75 1 0 27 76 1 0 27 77 1 0 29 78 1 0 29 79 1 0 29 80 1 0 30 81 1 0 34 82 1 0 34 83 1 0 34 84 1 0 37 85 1 0 M END

Standard InCHIKey	FRRMMEJOPQSLSE-HRGDRPPLSA-N
Standard InCHI	InChI=1S/C32H48O5/c1-19(28(35)36)9-11-25(37-21(3)33)20(2)22-13-17-32(8)24-10-12-26-29(4,5)27(34)15-16-30(26,6)23(24)14-18-31(22,32)7/h9-10,14,20,22,25-27,34H,11-13,15-18H2,1-8H3,(H,35,36)/b19-9+/t20-,22+,25-,26-,27+,30+,31+,32-/m0/s1
SMILES	C/C(=CC[C@@H]([C@@H](C)[C@H]1CC[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@@H](CC[C@]4(C)C3=CC[C@]12C)O)OC(=O)C)/C(=O)O

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO40141	Ganoderma sp. BCC 16642	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26716912]
NPO40141	Ganoderma sp. BCC 16642	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
MIC	1
IC50	1

Activity Type	# Activity
Cell line	1
Organism	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
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	>	98000.0	nM	PMID[26716912]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	50.0	ug.mL-1	PMID[26716912]

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 NPC141401 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	17131
0.1-0.2	25669
0.2-0.3	6345
0.3-0.4	580
0.4-0.5	71
0.5-0.6	36
0.6-0.7	15
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	Natural Product ID
0.7794	Intermediate Similarity	NPC489791
0.7681	Intermediate Similarity	NPC58410
0.7647	Intermediate Similarity	NPC276127
0.7647	Intermediate Similarity	NPC478307
0.7536	Intermediate Similarity	NPC478312
0.7313	Intermediate Similarity	NPC212948
0.7101	Intermediate Similarity	NPC214697
0.6712	Remote Similarity	NPC489808
0.6712	Remote Similarity	NPC489800
0.6447	Remote Similarity	NPC482571
0.6364	Remote Similarity	NPC166120
0.6329	Remote Similarity	NPC482569
0.6329	Remote Similarity	NPC146822
0.6316	Remote Similarity	NPC482568
0.6267	Remote Similarity	NPC39082
0.6267	Remote Similarity	NPC610107
0.6154	Remote Similarity	NPC482567
0.6133	Remote Similarity	NPC85742
0.6133	Remote Similarity	NPC22421
0.6053	Remote Similarity	NPC478301
0.6	Remote Similarity	NPC478313
0.6	Remote Similarity	NPC489790
0.5915	Remote Similarity	NPC475772
0.5897	Remote Similarity	NPC92022
0.5882	Remote Similarity	NPC205455
0.5857	Remote Similarity	NPC231310
0.5857	Remote Similarity	NPC202389
0.5811	Remote Similarity	NPC138536
0.5797	Remote Similarity	NPC6707
0.5753	Remote Similarity	NPC84271
0.5753	Remote Similarity	NPC222845
0.5753	Remote Similarity	NPC102414
0.5753	Remote Similarity	NPC296577
0.5733	Remote Similarity	NPC469406
0.5733	Remote Similarity	NPC484975
0.5733	Remote Similarity	NPC48647
0.5733	Remote Similarity	NPC321301
0.5714	Remote Similarity	NPC484797
0.5625	Remote Similarity	NPC489795
0.56	Remote Similarity	NPC45324
0.56	Remote Similarity	NPC162001
0.56	Remote Similarity	NPC77168
0.5556	Remote Similarity	NPC478309
0.5526	Remote Similarity	NPC186810
0.5385	Remote Similarity	NPC69982
0.5263	Remote Similarity	NPC87552
0.525	Remote Similarity	NPC489807
0.525	Remote Similarity	NPC478297
0.525	Remote Similarity	NPC478298
0.5244	Remote Similarity	NPC94393
0.52	Remote Similarity	NPC486193
0.5122	Remote Similarity	NPC489788
0.5122	Remote Similarity	NPC299325
0.507	Remote Similarity	NPC20853
0.507	Remote Similarity	NPC72507
0.506	Remote Similarity	NPC478311
0.5059	Remote Similarity	NPC241221
0.5059	Remote Similarity	NPC482570

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC141401 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5749
0.1-0.2	3266
0.2-0.3	130
0.3-0.4	5
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